CN103980218B - A kind of chiral oxazoline crystalline compounds and purposes - Google Patents
A kind of chiral oxazoline crystalline compounds and purposes Download PDFInfo
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- CN103980218B CN103980218B CN201410224498.XA CN201410224498A CN103980218B CN 103980218 B CN103980218 B CN 103980218B CN 201410224498 A CN201410224498 A CN 201410224498A CN 103980218 B CN103980218 B CN 103980218B
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- chiral oxazoline
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000013078 crystal Substances 0.000 claims abstract description 11
- -1 phenyl aldehyde Chemical class 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 2
- 238000002447 crystallographic data Methods 0.000 claims description 2
- 238000002050 diffraction method Methods 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 125000006850 spacer group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 15
- 238000003786 synthesis reaction Methods 0.000 abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 229960001701 chloroform Drugs 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 4
- 239000012046 mixed solvent Substances 0.000 abstract description 4
- 238000001953 recrystallisation Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 229910021529 ammonia Inorganic materials 0.000 abstract description 3
- 238000004440 column chromatography Methods 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract description 2
- 239000012074 organic phase Substances 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 7
- 239000003814 drug Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000006842 Henry reaction Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- MHQIZLXEJZNBQI-UHFFFAOYSA-N 1h-inden-1-amine Chemical class C1=CC=C2C(N)C=CC2=C1 MHQIZLXEJZNBQI-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 0 CC*(C)N=C(C*)C* Chemical compound CC*(C)N=C(C*)C* 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 238000006987 Nef reaction Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical group CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- QDYBCIWLGJMJGO-UHFFFAOYSA-N dinitromethanone Chemical compound [O-][N+](=O)C(=O)[N+]([O-])=O QDYBCIWLGJMJGO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005648 named reaction Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2217—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
A kind of chiral oxazoline crystalline compounds, its chemical formula is as follows:
, the synthesis of this chiral oxazoline crystalline compounds is in 100mL two-mouth bottle, under anhydrous and oxygen-free condition, adds anhydrous ZnCl
2?5.0g, 40ml chlorobenzene, adjacent diethyl itrile group benzene 5.0g (32.0mmol), chirality L-valerian ammonia alcohol 15.6g, at high temperature reflux mixture 72h, stopped reaction, reduces pressure with except desolventizing, by residuum water dissolution, and use CHCl
3(20mLx2) extract, organic phase anhydrous sodium sulfate drying, rotate except desolventizing, by thick product sherwood oil/methylene dichloride (1:1) column chromatography, obtain blue oily liquids (II), with sherwood oil, trichloromethane and alcohol mixed solvent recrystallization, obtain blue colored crystal (I); It shows good catalytic activity as catalyzer in the Henle reaction of phenyl aldehyde.
Description
One, technical field
The present invention relates to a kind of compound and preparation method thereof, particularly a kind of chipal compounds and preparation method thereof, is exactly a kind of chiral oxazoline crystalline compounds and synthetic method thereof.
Two, background technology
Optically pure compound has special property and outstanding function because of it, as D-amygdalic acid, L-amygdalic acid etc., by asymmetry catalysis, the composition of indusrial toxic side effect is rejected, produce the homochiral medicine with single oriented structure, thus make pharmaceutical cpd purer, when disease therapy, curative effect is faster, the course for the treatment of is shorter.Research one of new direction having become international new drug research at present of chiral drug, national governments and Ge great pharmaceuticals drop into huge fund one after another, and the research and development of chiral catalyst are one of gordian techniquies of chiral drug exploitation, therefore extremely pay attention to.21 century is century of chiral synthesize chemistry great development, calendar year 2001 Nobel chemistry Prize authorized three and made the scientist of significant contribution in asymmetry catalysis synthesis field, demonstrate the importance of this research field.Although there are many asymmetric catalysis to be applied to industrial production, find cheap and easy to get, efficient, that selectivity is good catalyzer and be conducive to producing and the process for catalytic synthesis of environment protection, remaining the major issue needing our research and solve.
In recent years, the miscellaneous bidentate of domestic and international latest report, three teeth and Si Chi oxazoline ligand etc. and metal complex catalysts
[2]to hydrogenation
[3-5], Heck reaction
[6-8], allyl group alkylated reaction
[9-11], Diels-Alder reaction
[12-13], zinc ethyl is to aldehyde
[14-15]addition reaction etc. there is extraordinary catalytic activity, thus paid close attention to widely.[1-15]
1. a life is brave, Guo Jianquan, asymmetric catalysis, Science Press .2002,1.
2.Cozzi,P.G.；Menges,F.；Kaiser,S.Synlett.2003,833.
3.Tang,W.；Wang,W.；Zhang,X.Angew.Chem.,Int.Ed.Engl.2003,42,943.
4.Xu,G.；Gilbertson,S.R.TetrahedronLett.2002,44,953.
5.Hilgraf,R.；Pfaltz,A.Synlett.1999,1814.
6.(a)Powell,M.T.；Hou,D.-R.；Perry,M.C.；Cui,X.；Burgess,K.J.Am.Chem.Soc.2001,123,8878.(b)Perry,M.C.；Cui,X.；Powell,M.T.；Hou,D.-R.；Reibenspies,J.H.；Burgess,K.J.Am.Chem.Soc.2003,125,113.
7.Gilbertson,S.R.；Xie,D.；Fu,Z.TetrahedronLett.2001,42,368.
8.Hashimoto,Y.；Horie,Y.；Hayashi,M.；Saigo,K.Tetrahedron:Asymmetry2000,11,2205.
9.Tu,T.；Deng,W.-P.；Hou,X.-L.；Dai,L.-X.；Dong,X.-C.Chem.Eur.J.2003,9,3073.
10.Gilbertson,S.R.；Xie,D.Angew.Chem.,Int.Ed.Engl.1999,38,2750.
11.Burgess,K.；Porte,A.M.Tetrahedron:Asymmetry1998,9,2465.
12.Bolm,C.；Xiao,L.；Kesselgruber,M.Org.Biomol.Chem.2003,1,145.
13.Watanabe,K.；Hirasawa,T.；Hiroi,K.Chem.Pharm.Bull.2002,50,372.
14.Wipf,P.；Wang,X.Org.Lett.2002,4,1197.
15.Schinneri,M.；Seitz,M.；Kaiser,A.；Reiser,O.Org.Lett.2001,3,4259.
Three, summary of the invention
The present invention is intended to particularly to prepare chiral drug for asymmetric synthesis field provides chipal compounds part needed for a kind of efficient chiral catalyst, and technical problem to be solved is selected corresponding raw material and sets up corresponding method synthesis of chiral catalyst ligand.
Alleged by the present invention chipal compounds be the compound shown in following chemical formula (I):
(I)。
Its chemical name: the amino indenes of N-2-hydroxyethyl-β (S)-R base-3-[(4 (S)-R base-4,5-dihydro)]-oxazolinyl-2-.
The synthetic method of chipal compounds (I) is synthesized in organic solvent with adjacent diethyl itrile group benzene and chirality L-amino alcohol under catalyzer existence condition, and chemical equation is as follows:
The synthetic method of this chipal compounds (I) comprises synthesis, abstraction and purification, and described synthesis is exactly that adjacent diethyl itrile group benzene and chirality L-valerian ammonia alcohol have ZnCl in chlorobenzene
2when existing under anhydrous and oxygen-free condition back flow reaction 72 hours, ZnCl
2consumption is the 115mol% (weight percent, lower same) of material quantity adjacent diethyl itrile group benzene; Column chromatography for separation, with sherwood oil/methylene dichloride (1/1) wash-out, the first component point collected is volatilized naturally, obtains blue oily liquids (II), with sherwood oil, trichloromethane and alcohol mixed solvent recrystallization, obtain blue colored crystal (I).
The preparation of this chipal compounds, adopts simple and easy, efficient methodology of organic synthesis, the blue oily liquids (II) of one-step synthesis chipal compounds, with sherwood oil, trichloromethane and alcohol mixed solvent recrystallization, obtain blue colored crystal (I) crystal, and characterize its structure with X-diffraction.
Henry reaction is one of organic name reaction of classics.This reaction refers to the condensation reaction of carbonyl compound normally between aromatic aldehyde and the nitro-compound having α-hydrogen, and the result of reaction is that the alpha-carbon atom of nitro adds on carbonyl, forms the compound of bifunctional with hydroxyl, nitro.The product of Henry reaction can be converted into the compound having important use of all kinds, easily as beta-alkamine, nitroolefin, nitroketone, nitro ketenes or carry out Nef reaction.Therefore Henry reaction is one of very practical reaction in organic synthesis.Expand the range of application of this reaction, synthesis has compound more complicated in more polyfunctional group, structure, is a significant job.
To be a kind of chiral oxazoline crystalline compounds show good catalytic activity to purposes alleged by the present invention in it is as the Henle reaction of catalyzer at phenyl aldehyde.
Four, accompanying drawing explanation
Fig. 1 is the X-diffraction analysis figure of crystalline compounds I.
Five, embodiment
The preparation of the amino indenes of 1-2-hydroxyethyl-β (S)-sec.-propyl-3-[4 (S)-(sec.-propyl)-4,5-dihydro]-oxazolinyl-2-
(Compound I)
In 100mL two-mouth bottle, under anhydrous and oxygen-free condition, add anhydrous ZnCl
25.0g, 40ml chlorobenzene, adjacent diethyl itrile group benzene 5.0g (32.0mmol), chirality L-valerian ammonia alcohol 15.6g, at high temperature reflux mixture 72h, stopped reaction, reduces pressure with except desolventizing, by residuum water dissolution, and use CHCl
3(20mLx2) extract, organic phase anhydrous sodium sulfate drying, rotate except desolventizing, by thick product sherwood oil/methylene dichloride (1:1) column chromatography, obtain blue oily liquids, with sherwood oil, trichloromethane and alcohol mixed solvent recrystallization, obtain blue colored crystal, productive rate 82%, [a]
5 d=-114.59 ° of (c=0.06, CHCl
3);
1hNMR (500MHz, CDCl
3, 27 DEG C), δ (ppm)=7.52 (d, J=8Hz, 1H), 7.18 (t, J=0.5Hz, 2H), 6.90 (t, J=4.32Hz, 1H), 4.30 (t, J=0Hz, 1H), 3.95 ~ 4.04 (m, 3H), 3.33 ~ 3.74 (m, 5H), 3.31 (d, J=3.5Hz, 1H), 1.89 ~ 1.90 (m, 1H), 1.69 ~ 1.71 (m, 1H) .0.89 ~ 0.97 (m, 12H).
13cNMR17.86,18.61,18.73,19.92,30.32,33.55,36.77 (x2), 63.25,64.34,69.25,70.89,118.23,120.77,122.99,127.07,133.66,144.01,164.44 (x2) .IR:3062,2956,2921,2870,2850,2249,1720,1659,1655,1617,1604,1492,1463,1378,1290,1205,1073,1027,909,759,735,700,648; Elementalanalysis:found:N:8.54%, C:73.40%, H:8.48%; Calculate:N:8.53%, C:73.14%, H:8.59%.IR:3062,3030,2956,2921,2850,2870,1720,1659,1617,1604,1492,1463,1378,1290,1205,1073,1027,909,759,700,505.These compound crystal data are as follows:
Empirical formula C20H28N2O2
Molecular weight 328.44
Temperature 133 (2) K
Wavelength 0.71073A
Crystallographic system, Space group Monoclinic system, P2 (1) 2 (1) 2 (1)
Unit cell parameters a=16.527 (2) Aalpha=90deg.
b＝19.751(3)Abeta＝90deg.
c＝27.075(4)Agamma＝90deg.
Volume 8838 (2) A^3
Electric density 16,0.987Mg/m^3
Absorption correction parameter 0.064mm^-1
Number of electrons 2848 in unit cell
Crystallographic dimension 0.20x0.15x0.10mm
The scope 1.28to25.05 at Theta angle
Index capture range-the 19<=h<=19 of HKL ,-23<=k<20 ,-32<=l<=32
Collection/independent diffraction data 56068/15660 [R (int)=0.1095]
The data integrity degree 99.9% of theta=30.5
The method Multi Slice Mode of absorption correction
The transmitance 0.9937and0.9874 of minimax
The Matrix least square method of the method F^2 that refine uses
Number/the number of parameters 15660/5/865 of data number/use restriction
The method 0.952 that refine uses
The consistence factor R 1=0.0670 of point diffraction, wR2=0.1239
Identical factor R 1=0.1324, the wR2=0.1440 of observable diffraction
Absolute configuration parameter 1.4 (12)
Maximum summit on difference Fourier figure and peak valley 0.174and-0.171e.A^-3
The typical bond distance's data of crystal:
The typical bond angle data of crystal:
2, Henle reaction application
Get the crystalline compounds (I) (catalytic amount is 20%) of 0.20mmol and fluid cpds (II) respectively in the little flask of 25mL, add the absolute methanol solution of 2 milliliters, then, the phenyl aldehyde of 0.1mL and the Nitromethane 99Min. of 0.5mL is added in above-mentioned solution, stirring at room temperature, reacts after 6 hours, carries out nmr analysis, transformation efficiency: 56.8%, 40.6%;
1hNMR (300MHz, CDCl
3) 7.28 ~ 7.32 (m, 5H, Ar-H), 5.32 ~ 5.35 (d, J=9.18Hz, 1H ,-CH), 4.38 ~ 4.56 (m, 2H ,-CH
2), 3.89 (br, 1H ,-OH).
Claims (1)
1. the purposes of a chiral oxazoline crystalline compounds in the Henle reaction of phenyl aldehyde, it is characterized in that, the chiral oxazoline crystalline compounds getting 0.20mmol, in the flask of 25mL, adds the absolute methanol solution of 2mL, then, the phenyl aldehyde of 0.1mL and the Nitromethane 99Min. of 0.5mL is added in above-mentioned solution, stirring at room temperature, reacts after 6 hours, carries out nmr analysis, transformation efficiency: 56.8%, described chiral oxazoline crystalline compounds structure is:
This chiral oxazoline crystalline compounds at 273 (2) k temperature, on the X-ray single crystal diffraction instrument of Oxford, with the MoKa ray through graphite monochromator monochromatization
collect diffraction data with ω-θ scan mode, have the crystal X-diffraction analysis figure shown in Fig. 1, this crystal belongs to rhombic system, spacer P2 (1) 2 (1) 2 (1), unit cell parameters:
α=90 °;
β=90 °;
γ=90 °.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2272853A1 (en) * | 2008-04-25 | 2011-01-12 | Zhejiang Jiuzhou Pharmaceutical Co., Ltd. | Spiro phosphorus-oxazoline, synthesis and use thereof |
| CN102010443A (en) * | 2010-10-25 | 2011-04-13 | 罗梅 | Chiral phosphonous bis-amino-oxazoline copper complex and synthesis method thereof |
| CN103319428A (en) * | 2013-07-07 | 2013-09-25 | 罗梅 | Chiral oxazoline and synthesis method thereof |
| CN103351400A (en) * | 2013-07-21 | 2013-10-16 | 罗梅 | Chiral double oxazoline copper complex and synthetic method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2272853A1 (en) * | 2008-04-25 | 2011-01-12 | Zhejiang Jiuzhou Pharmaceutical Co., Ltd. | Spiro phosphorus-oxazoline, synthesis and use thereof |
| CN102010443A (en) * | 2010-10-25 | 2011-04-13 | 罗梅 | Chiral phosphonous bis-amino-oxazoline copper complex and synthesis method thereof |
| CN103319428A (en) * | 2013-07-07 | 2013-09-25 | 罗梅 | Chiral oxazoline and synthesis method thereof |
| CN103351400A (en) * | 2013-07-21 | 2013-10-16 | 罗梅 | Chiral double oxazoline copper complex and synthetic method thereof |
Non-Patent Citations (1)
| Title |
|---|
| Modular Synthesis of Oxazolines and Their Derivatives;Luo Mei等;《J.Comb.Chem.》;20091201;第11卷(第2期);第222页图1、第223页左栏倒数第2段、第226页左栏最后1段至右栏第1段 * |
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