CN104263796A - Preparation method of R-1-aminotetralin - Google Patents
Preparation method of R-1-aminotetralin Download PDFInfo
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- CN104263796A CN104263796A CN201410463547.5A CN201410463547A CN104263796A CN 104263796 A CN104263796 A CN 104263796A CN 201410463547 A CN201410463547 A CN 201410463547A CN 104263796 A CN104263796 A CN 104263796A
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- tetrahydro naphthylamine
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- optical purity
- naphthylamine
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- JRZGPXSSNPTNMA-SNVBAGLBSA-N (1r)-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2[C@H](N)CCCC2=C1 JRZGPXSSNPTNMA-SNVBAGLBSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 claims abstract description 18
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims abstract description 16
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims abstract description 14
- 230000003287 optical effect Effects 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 108010084311 Novozyme 435 Proteins 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 229960002510 mandelic acid Drugs 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 238000005576 amination reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000006340 racemization Effects 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 102000018120 Recombinases Human genes 0.000 abstract 1
- 108010091086 Recombinases Proteins 0.000 abstract 1
- DQVWXLRNCXQVKH-SECBINFHSA-N acetyl (2r)-2-hydroxy-2-phenylacetate Chemical compound CC(=O)OC(=O)[C@H](O)C1=CC=CC=C1 DQVWXLRNCXQVKH-SECBINFHSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 238000006268 reductive amination reaction Methods 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention relates to a preparation method of R-1-aminotetralin. The preparation method comprises the following steps: taking 1-tetralone (I) as a raw material and KT-02 (nickel type) as a catalyst to carry out reductive amination under the condition of high pressure to obtain 1-aminotetralin (II); after obtaining II, introducing hydrogen to an autoclave to resolve II by using Novozym435 as resolvase, D-(-)-O-acetylmandelic acid as an acyl donor and KT-02 as a racemisation catalyst and completely transforming II to obtain a compound III (with ee value of 99%); after purifying III, carrying out acidolysis on III to obtain a compound IV and alkalifying, extracting, drying and concentrating IV to obtain R-1-aminotetralin (V), wherein the product yield is over 90% and the ee value is more than 99% in each step. The preparation method has the characteristics of cheap and accessible catalyst, full utilization of the raw material, good product yield, high optical purity, and the like and has great guidance and application values in production and preparation of R-1-aminotetralin.
Description
Technical field
The present invention relates to a kind of preparation method of optical homochiral amine, particularly relate to the preparation method of optical purity R-1-tetrahydro naphthylamine.
Background technology
R-1-tetrahydro naphthylamine, as important medicinal intermediates, has a wide range of applications in new drug synthesis field.In recent years, the great interest of medicament research and development personnel is caused.It is the important intermediate that protein inhibitor of dying is adjusted in synthesis.Adjusting dies is one of mechanism of necrocytosis, utilizes this effect can Therapeutic cancer, senile dementia and autoimmune conditions etc. effectively.
At present, prepare R-1-tetrahydro naphthylamine and generally adopt first preparation 1-tetrahydro naphthylamine racemic modification (USP2001003136.2001-07-07; Bio.Med.Chem.2004.12 (15):
Method 4189-4196) split again, also has (the J.Org.Chem.2006.71.6859-6862 adopting asymmetric catalysis to obtain optical purity 1-tetrahydro naphthylamine; Tetrahedron Asym.1998.9,4369-4379).But all there is the problems such as the low and the finished product optical purity of product yield is bad in these methods reported.
Summary of the invention
The technical problem to be solved in the present invention is that R-1-tetrahydro naphthylamine was preparing the high yield in planting and high-optical-purity.
In order to solve the problem, the invention provides a kind of preparation method of optical purity R-1-tetrahydro naphthylamine: 1) in autoclave, add ALPHA-tetralone (I) and anhydrous methanol in the ratio of mass volume ratio 1:5-10, then add KT-02(ni-type catalyzer in the ratio of ALPHA-tetralone massfraction 1%-10%); Air passes into liquefied ammonia in the ratio of 50%-80%, passes into hydrogen to pressure 2-5MPa in last autoclave after getting rid of, and heats up and reacts; After TLC detection ALPHA-tetralone transforms completely, terminate reaction, concentrated, obtain 1-tetrahydro naphthylamine (II); 2) in autoclave, take toluene as solvent, the ratio of 1:1.0-2.0 adds raw material 1-tetrahydro naphthylamine and acry radical donor D-(-)-O-ethanoyl amygdalic acid in molar ratio, then lipase Novozym 435 and KT-02 is added in the ratio of raw material 1-tetrahydro naphthylamine massfraction 1%-10%, after nitrogen replacement is carried out in autoclave sealing, pass into hydrogen to pressure 0.1-1.0MPa and be warming up to 40-70 DEG C reaction 24 hours, 1-tetrahydro naphthylamine can be converted into compound completely, and product ee value reaches 99%; After reaction terminates, solution is concentrated, column chromatography, obtain compound III sterling; 3) be dissolved in the alcohol of 10 times of volume ratios and the mixing solutions of acid solution (v/v=1:1) by compound III sterling obtained in step 2, then heating reflux reaction 15 hours, compound III complete hydrolysis obtains compounds Ⅳ; 4) step 3 gained compounds Ⅳ is carried out alkalinisation treatment, then by organic solvent extraction, drying, concentrated can obtain optically pure R-1-tetrahydro naphthylamine, final whole step product yield can reach more than 90%, and optical purity of products is 99%.
The present invention is in preparation R-1-tetrahydro naphthylamine process, and use KT-02 as reduction amination catalyzer and racemization catalyst, have catalyzer cheap and easy to get, use safety, catalytic efficiency is good, transformation efficiency advantages of higher.1-tetrahydro naphthylamine is that acry radical donor can ensure under the condition of high transformation efficiency with D-(-)-O-ethanoyl amygdalic acid in split process, and optical purity of products might as well.
Specific implementation method:
1) preparation of 1-tetrahydro naphthylamine
In the autoclave of 2000ML, add 146G Tetralone an intermediate of Sertraline (I), 1000ML anhydrous methanol, 15GKT-02; After nitrogen replacement excluding air, pass into 102G liquefied ammonia, pass into hydrogen in last autoclave to pressure 5MPa, be warmed up to 80 DEG C and react; After TLC detection ALPHA-tetralone transforms completely, terminate reaction, filter, concentrate, obtain 1-tetrahydro naphthylamine (II) 145G;
2) preparation of compound III
1000mL toluene is added as solvent in the autoclave of 2000mL, add 117.6g1-tetrahydro naphthylamine, 172g D-(-)-O-ethanoyl amygdalic acid successively, 10g lipase Novozym 435 and 12gKT-02, after adding, with nitrogen, air in still is replaced after sealing autoclave, then in autoclave, pass into hydrogen to pressure 1.0MP, open and stir, and be warming up to 70 DEG C and react; After 24 hours, sampling detects, and 1-tetrahydro naphthylamine disappears and is converted into compound III completely, and product ee value reaches 99%; After reaction terminates, concentrated by solution, be then that the normal hexane of 10:1 and alcohol mixed solvent carry out column chromatography by volume ratio, obtain pure compound III 144.2G, yield is 95.4%.
3) compound III acidolysis obtains compounds Ⅳ
Joined by compound III 94.6g obtained in upper step in the solution that the ethanol of 1000ml and concentrated hydrochloric acid mix with volume ratio 1:1, then reflux, reacted after 12 hours, put plate detection compound III complete hydrolysis and obtained compounds Ⅳ.
4) alkalization obtains R-1-tetrahydro naphthylamine (V)
The solution that past step 3 gained reacts completely adds the methylene dichloride of 500mL, then slowly sodium hydroxide solution is dripped, and stir, detect solution pH value to 13, stop adding sodium hydroxide solution, separatory, upper water liquid uses the dichloromethane extraction 3 times of 200mL again, carry out drying by extracting the dichloromethane solution anhydrous sodium sulphate obtained several times, concentrated to obtain R-1-tetrahydro naphthylamine (V) 67.7g, yield is the ee value that 92.1%, HPLC detects the finished product is 99.5%.
Claims (5)
1. the preparation method of optical purity R-1-tetrahydro naphthylamine is characterized in that: 1) in autoclave, add ALPHA-tetralone (I) and anhydrous methanol in the ratio of mass volume ratio 1:5-10, then add KT-02 in the ratio of ALPHA-tetralone massfraction 5%-20%; Air passes into liquefied ammonia in the ratio of I quality 50%-80%, passes into hydrogen to pressure 2-5MPa in last autoclave after getting rid of, and heats up and reacts; After TLC detection ALPHA-tetralone transforms completely, terminate reaction, concentrated, obtain 1-tetrahydro naphthylamine (II); 2) in autoclave, take toluene as solvent, the ratio of 1:1.0-2.0 adds raw material 1-tetrahydro naphthylamine and acry radical donor D-(-)-O-ethanoyl amygdalic acid in molar ratio, then lipase Novozym 435 and Raney's nickel is added in the ratio of raw material 1-tetrahydro naphthylamine massfraction 1%-10%, after nitrogen replacement is carried out in autoclave sealing, pass into hydrogen to pressure 0.1-1.0MPa and be warming up to 40-70 DEG C reaction 24 hours, 1-tetrahydro naphthylamine is converted into compound III completely, and product ee value reaches 99%; After reaction terminates, solution is concentrated, column chromatography, obtain compound III sterling; 3) be dissolved in the alcohol of 10 times of volume ratios and the mixing solutions of acid solution (v/v=1:1) by compound III sterling obtained in step 2, then heating reflux reaction 12 hours, compound III complete hydrolysis obtains compounds Ⅳ; 4) step 3 gained compounds Ⅳ is carried out alkalinisation treatment, then by organic solvent extraction, drying, concentrated can obtain optically pure R-1-tetrahydro naphthylamine, final each step product yield all can reach more than 90%, and optical purity of products is 99%; According to described, its reaction equation is as follows:
。
2. according to claim 1, the preparation method of optical purity R-1-tetrahydro naphthylamine is characterized in that step 1) in reduction amination catalyzer used be KT-02.
3. according to claim 1, the preparation method of optical purity R-1-tetrahydro naphthylamine is characterized in that step 2) in acry radical donor be D-(-)-O-ethanoyl amygdalic acid, racemization catalyst is KT-02.
4. according to claim 1, the preparation method of optical purity R-1-tetrahydro naphthylamine is characterized in that step 3) in alcohol be methyl alcohol or ethanol; Acid is hydrochloric acid or sulfuric acid.
5. according to claim 1, the preparation method of optical purity R-1-tetrahydro naphthylamine is characterized in that step 4) in alkalinisation treatment alkali used be sodium hydroxide, potassium hydroxide or ammoniacal liquor; Extracting organic solvent used is toluene, methylene dichloride, 1,2-ethylene dichloride, ether etc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410463547.5A CN104263796B (en) | 2014-09-12 | 2014-09-12 | A kind of preparation method of the tetrahydro naphthylamines of R 1 |
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| CN201410463547.5A CN104263796B (en) | 2014-09-12 | 2014-09-12 | A kind of preparation method of the tetrahydro naphthylamines of R 1 |
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| CN104263796A true CN104263796A (en) | 2015-01-07 |
| CN104263796B CN104263796B (en) | 2018-01-26 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105063161A (en) * | 2015-08-18 | 2015-11-18 | 陈永军 | Method for preparing R-1-aminoindan |
| CN105087742A (en) * | 2015-08-18 | 2015-11-25 | 陈永军 | Method for preparing R-6-hydroxy-1-aminoindane through dynamic kinetic resolution |
| CN106380408A (en) * | 2016-09-04 | 2017-02-08 | 王际菊 | Preparation of optical homochiral amine |
| CN106381324A (en) * | 2016-09-04 | 2017-02-08 | 王际菊 | Preparation method of R-7-chloro-1-tetralinylamine |
| CN106397217A (en) * | 2016-09-04 | 2017-02-15 | 王际菊 | Method for synthesizing dextral alpha-cyclohexylbenzylamine |
| CN106480117A (en) * | 2016-09-04 | 2017-03-08 | 王际宽 | The synthesis of 6 methoxyl group 1 tetralin amine and fractionation |
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| JP2001149089A (en) * | 1999-11-26 | 2001-06-05 | Sumitomo Chem Co Ltd | Method for producing optically active amino compound |
| CN102766672A (en) * | 2011-05-06 | 2012-11-07 | 王际宽 | Kinetic resolution method of chiral amine |
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2014
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Patent Citations (2)
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| JP2001149089A (en) * | 1999-11-26 | 2001-06-05 | Sumitomo Chem Co Ltd | Method for producing optically active amino compound |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105063161A (en) * | 2015-08-18 | 2015-11-18 | 陈永军 | Method for preparing R-1-aminoindan |
| CN105087742A (en) * | 2015-08-18 | 2015-11-25 | 陈永军 | Method for preparing R-6-hydroxy-1-aminoindane through dynamic kinetic resolution |
| CN105087742B (en) * | 2015-08-18 | 2018-09-14 | 陈永军 | Dynamic Kinetic Resolution prepares R-6- hydroxyl -1- aminoidans |
| CN105063161B (en) * | 2015-08-18 | 2018-11-09 | 陈永军 | A kind of preparation method of R-1- aminoidans |
| CN106380408A (en) * | 2016-09-04 | 2017-02-08 | 王际菊 | Preparation of optical homochiral amine |
| CN106381324A (en) * | 2016-09-04 | 2017-02-08 | 王际菊 | Preparation method of R-7-chloro-1-tetralinylamine |
| CN106397217A (en) * | 2016-09-04 | 2017-02-15 | 王际菊 | Method for synthesizing dextral alpha-cyclohexylbenzylamine |
| CN106480117A (en) * | 2016-09-04 | 2017-03-08 | 王际宽 | The synthesis of 6 methoxyl group 1 tetralin amine and fractionation |
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