CN111777500A - Synthesis process of cis-jasmonone - Google Patents
Synthesis process of cis-jasmonone Download PDFInfo
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Abstract
本发明涉及一种顺式茉莉酮合成工艺，具体通过包括环戊二烯和乙烯酮反应生成7,7‑二氯二环(3.2.0)庚‑2‑烯‑6‑酮，再通过一类型反应最终生成3‑甲基‑2‑(顺‑2‑戊烯基)‑2‑环戊烯酮。本发明方法合成路线清晰，不涉及到常规方法中的溴元素，且工艺难度小，有利于大规模生产应用。
The invention relates to a process for synthesizing cis-jasmone, which specifically comprises the steps of reacting cyclopentadiene and ketene to generate 7,7-dichlorobicyclo(3.2.0)hept-2-ene-6-ketone, and then passing a This type of reaction eventually yields 3-methyl-2-(cis-2-pentenyl)-2-cyclopentenone. The method of the invention has a clear synthetic route, does not involve the bromine element in the conventional method, and has low technological difficulty, which is favorable for large-scale production and application.
Description
技术领域technical field
本发明涉及一种顺式茉莉酮合成工艺。The invention relates to a synthesis process of cis-jasmone.
背景技术Background technique
顺式茉莉酮是一种应用广泛的重要香料，其香气似茉莉花香，是茉莉油的重要香成份之一，主要用于高级茉莉系列化妆品香精中，其对应的分子式为C11H16O。Cis-jasmone is an important spice widely used. Its aroma is like jasmine flower, and it is one of the important aroma components of jasmine oil. It is mainly used in high-grade jasmine series cosmetic essences.
目前，关于顺式茉莉酮的合成已有较多的报导，但多数都仅停留在实验室合成阶段，能真正能用于工业化生产的极少。一般的，工业生产上，目前国内外较为常用的方法包括如下几个步骤：(1)2-甲基呋喃和丙烯醛反应得到3-(5-甲基-2-呋喃基)丙醛；(2)1-溴丙烷和三苯基膦反应得到正丙基三苯基溴化鏻盐；(3)正丙基三苯基溴化鏻盐和氢化钠或叔丁醇钾或氨基钠反应得到正丙基三苯基膦叶立德；(4)正丙基三苯基膦叶立德和3-(5-甲基-2-呋喃基)丙醛反应，得到顺式为主的5-甲基-2-(3-己烯基)呋喃；(5)顺式-5-甲基-2-(3-己烯基)呋喃在酸性条件下开环得到顺式十一碳-8-烯-2，5-二酮；(6)顺式十一碳-8-烯-2，5-二酮在碱性条件下缩合关环得到顺式茉莉酮–顺式3-甲基-2-(2-戊烯基)环戊-2-烯酮。但是该反应用到大量的卤素，同时反应时间过长，不宜采用。At present, there have been many reports on the synthesis of cis-jasmonone, but most of them are only in the laboratory synthesis stage, and very few can really be used for industrial production. Generally, in industrial production, the more commonly used methods at home and abroad include the following steps: (1) 2-methylfuran and acrolein are reacted to obtain 3-(5-methyl-2-furanyl)propanal; ( 2) 1-bromopropane and triphenylphosphine react to obtain n-propyl triphenyl phosphonium bromide salt; (3) n-propyl triphenyl phosphonium bromide salt and sodium hydride or potassium tert-butoxide or sodium amide react to obtain n-propyl triphenyl phosphine ylide; (4) n-propyl triphenyl phosphine ylide reacts with 3-(5-methyl-2-furyl) propanal to obtain cis-based 5-methyl-2 -(3-hexenyl)furan; (5)cis-5-methyl-2-(3-hexenyl)furan was ring-opened under acidic conditions to obtain cis-undec-8-ene-2, 5-dione; (6) cis-undec-8-ene-2,5-dione was condensed and closed under alkaline conditions to obtain cis-jasmonone-cis-3-methyl-2-(2- pentenyl) cyclopent-2-enone. However, this reaction uses a large amount of halogen, and the reaction time is too long, so it is not suitable for use.
发明内容SUMMARY OF THE INVENTION
为解决上述技术问题，本发明的目的是提供一种顺式茉莉酮合成工艺。In order to solve the above-mentioned technical problems, the object of the present invention is to provide a kind of cis-jasmonone synthesis process.
本发明的技术方案如下：The technical scheme of the present invention is as follows:
顺式茉莉酮合成工艺，其特征在于，包括如下步骤：Synthesis process of cis-jasmone, is characterized in that, comprises the steps:
S1、通过环戊二烯和乙烯酮反应生成7,7-二氯二环(3.2.0 )庚-2-烯-6-酮；S1, through the reaction of cyclopentadiene and ketene to generate 7,7-dichlorobicyclo(3.2.0)hept-2-en-6-one;
S2、通过7,7-二氯二环(3.2.0 )庚-2-烯-6-酮在和Zn、醋酸发生取代反应生成双环[3,2,0]庚-2-烯-6-酮；S2, by 7,7-dichlorobicyclo(3.2.0)hept-2-en-6-one, it undergoes substitution reaction with Zn and acetic acid to generate bicyclo[3,2,0]hept-2-ene-6- ketone;
S3、双环[3,2,0]庚-2-烯-6-酮通过和醋酸双氧水反应生成3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮；S3. Bicyclo[3,2,0]hept-2-en-6-one is reacted with acetic acid hydrogen peroxide to generate 3,3a,4,6a tetrahydro-2H-cyclopentadieno[b]furan-2-one ;
S4、3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮通过和氢化锂加成反应生成3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇；S4, 3,3a,4,6a tetrahydro-2H-cyclopentadieno[b]furan-2-one was added to 3,3a,6,6a-tetrahydro-2H-cyclopentanone with lithium hydride [b] furan-2-ol;
S5、3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇通过和三苯基-亚乙基膦反应生成(Z) -2-(2-戊烯基) -3-环戊烯-1-醇；S5, 3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-ol was reacted with triphenyl-ethylidene phosphine to form (Z)-2-(2-pentenyl) -3-cyclopenten-1-ol;
S6、(Z) -2-(2-戊烯基) -3-环戊烯-1-醇通过和双氧水反应生成（Z） -2-（2-戊烯基）-2-环戊烯-1-酮；S6, (Z)-2-(2-pentenyl)-3-cyclopenten-1-ol reacts with hydrogen peroxide to generate (Z)-2-(2-pentenyl)-2-cyclopentene- 1-keto;
S7、（Z）-2-（2-戊烯基）-2-环戊烯-1-酮通过和甲基锂反应生成（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇；S7, (Z)-2-(2-pentenyl)-2-cyclopenten-1-one reacts with methyl lithium to generate (Z)-1-methyl-2-(2-pentenyl) -2-cyclopenten-1-ol;
S8、（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇通过和氧化铬盐酸反应生成(Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮。S8, (Z)-1-methyl-2-(2-pentenyl)-2-cyclopenten-1-ol reacts with chromium oxide hydrochloric acid to generate (Z)-3-methyl-2-(2 -pentenyl)-2-cyclopenten-1-one.
进一步的，所述步骤S1中反应温度为40-60℃，压力为常压，反应时间为30-60分钟。Further, in the step S1, the reaction temperature is 40-60° C., the pressure is normal pressure, and the reaction time is 30-60 minutes.
进一步的，所述步骤S2中醋酸为过量。Further, in the step S2, the acetic acid is excessive.
进一步的，所述步骤S3中，还持续通入氧气直至反应结束。Further, in the step S3, oxygen is also continuously introduced until the reaction ends.
进一步的，所述步骤S4为在氮气保护下进行。Further, the step S4 is performed under nitrogen protection.
进一步的，所述步骤S5中反应温度为50-60℃，压力为常压，反应时间为3-5分钟。Further, in the step S5, the reaction temperature is 50-60° C., the pressure is normal pressure, and the reaction time is 3-5 minutes.
进一步的，所述步骤S6中反应温度为50-60℃，压力为3个标准大气压，反应时间为15-20分钟。Further, in the step S6, the reaction temperature is 50-60° C., the pressure is 3 standard atmospheric pressures, and the reaction time is 15-20 minutes.
进一步的，还包括持续通入氧气。Further, it also includes continuous infusion of oxygen.
进一步的，所述步骤S7为在氮气保护下进行。Further, the step S7 is performed under nitrogen protection.
进一步的，所述步骤S8为在负压下反应生成，负压为0.3个标准大气压。Further, the step S8 is to react and generate under negative pressure, and the negative pressure is 0.3 standard atmospheric pressure.
借由上述方案，本发明至少具有以下优点：By means of the above scheme, the present invention has at least the following advantages:
本发明方法合成路线清晰，不涉及到常规方法中的溴元素，且工艺难度及制备均低，有利于大规模生产应用。The method of the invention has a clear synthetic route, does not involve the bromine element in the conventional method, and has low technological difficulty and preparation, which is favorable for large-scale production and application.
上述说明仅是本发明技术方案的概述，为了能够更清楚了解本发明的技术手段，并可依照说明书的内容予以实施，以下以本发明的较佳实施例并详细说明如后。The above description is only an overview of the technical solution of the present invention. In order to understand the technical means of the present invention more clearly and implement it according to the content of the description, the preferred embodiments of the present invention are described below in detail.
附图说明Description of drawings
为了更清楚地说明本发明实施例的技术方案，下面将对实施例中所需要使用的附图作简单地介绍，应当理解，以下附图仅示出了本发明的某个实施例，因此不应被看作是对范围的限定，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他相关的附图。In order to illustrate the technical solutions of the embodiments of the present invention more clearly, the following briefly introduces the accompanying drawings that need to be used in the embodiments. It should be regarded as a limitation of the scope, and for those of ordinary skill in the art, other related drawings can also be obtained according to these drawings without any creative effort.
图1是本发明反应方程式。Fig. 1 is the reaction equation of the present invention.
具体实施方式Detailed ways
下面结合附图和实施例，对本发明的具体实施方式作进一步详细描述。以下实施例用于说明本发明，但不用来限制本发明的范围。The specific embodiments of the present invention will be described in further detail below with reference to the accompanying drawings and embodiments. The following examples are intended to illustrate the present invention, but not to limit the scope of the present invention.
实施例1Example 1
取1mol环戊二烯和1mol乙烯酮在反应温度为40℃，压力为常压，反应时间为30-60分钟，生成7,7-二氯二环(3.2.0 )庚-2-烯-6-酮；通过7,7-二氯二环(3.2.0 )庚-2-烯-6-酮在和2molZn、过量醋酸发生取代反应生成双环[3,2,0]庚-2-烯-6-酮；在双环[3,2,0]庚-2-烯-6-酮通过和过量醋酸1mol双氧水反应生成3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮，反应过程中持续通入氧气；3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮通过和2mol氢化锂加成反应生成3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇，反应过程在氮气保护下进行；3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇通过和1mol三苯基-亚乙基膦反应生成(Z) -2-(2-戊烯基) -3-环戊烯-1-醇，反应温度为500℃，压力为常压，反应时间为3分钟。 (Z) -2-(2-戊烯基) -3-环戊烯-1-醇通过和1mol双氧水反应生成（Z） -2-（2-戊烯基）-2-环戊烯-1-酮，反应温度为50℃，压力为3个标准大气压，反应时间为15分钟；（Z）-2-（2-戊烯基）-2-环戊烯-1-酮通过和1mol甲基锂反应生成（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇，在氮气保护下进行；（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇通过和1mol氧化铬1mol盐酸反应生成(Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮，在负压下反应生成，负压为0.3个标准大气压。生成0.75mol(Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮。Take 1mol of cyclopentadiene and 1mol of ketene at the reaction temperature of 40 ° C, the pressure is normal pressure, and the reaction time is 30-60 minutes to generate 7,7-dichlorobicyclo(3.2.0) hept-2-ene- 6-keto; Bicyclo[3,2,0]hept-2-ene is generated by 7,7-dichlorobicyclo(3.2.0)hept-2-en-6-one substitution reaction with 2mol Zn and excess acetic acid -6-keto; in bicyclo[3,2,0]hept-2-en-6-one, 3,3a,4,6a tetrahydro-2H-cyclopentadieno[b was generated by reacting with excess acetic acid 1mol hydrogen peroxide ]furan-2-one, oxygen was continuously introduced during the reaction; 3,3a,4,6atetrahydro-2H-cyclopentadieno[b]furan-2-one was added to 2mol lithium hydride to generate 3 ,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-ol, the reaction process was carried out under nitrogen protection; 3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan -2-ol is reacted with 1 mol of triphenyl-ethylidene phosphine to generate (Z)-2-(2-pentenyl)-3-cyclopenten-1-ol. The reaction temperature is 500 °C and the pressure is normal pressure, and the reaction time was 3 minutes. (Z)-2-(2-pentenyl)-3-cyclopenten-1-ol was reacted with 1mol hydrogen peroxide to generate (Z)-2-(2-pentenyl)-2-cyclopenten-1 -ketone, the reaction temperature was 50 °C, the pressure was 3 standard atmospheres, and the reaction time was 15 minutes; (Z)-2-(2-pentenyl)-2-cyclopenten-1-one was passed through and 1 mol methyl Lithium reacts to generate (Z)-1-methyl-2-(2-pentenyl)-2-cyclopenten-1-ol, which is carried out under nitrogen protection; (Z)-1-methyl-2-( 2-pentenyl)-2-cyclopenten-1-ol was reacted with 1 mol of chromium oxide and 1 mol of hydrochloric acid to generate (Z)-3-methyl-2-(2-pentenyl)-2-cyclopentene- The 1-ketone is formed by the reaction under negative pressure, and the negative pressure is 0.3 standard atmosphere. 0.75 mol of (Z)-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one was produced.
实施例2Example 2
取1mol环戊二烯和1mol乙烯酮在反应温度为40-60℃，压力为常压，反应时间为40分钟，生成7,7-二氯二环(3.2.0 )庚-2-烯-6-酮；通过7,7-二氯二环(3.2.0 )庚-2-烯-6-酮在和2molZn、过量醋酸发生取代反应生成双环[3,2,0]庚-2-烯-6-酮；在双环[3,2,0]庚-2-烯-6-酮通过和过量醋酸1mol双氧水反应生成3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮，反应过程中持续通入氧气；3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮通过和2mol氢化锂加成反应生成3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇，反应过程在氮气保护下进行；3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇通过和1mol三苯基-亚乙基膦反应生成(Z) -2-(2-戊烯基) -3-环戊烯-1-醇，反应温度为55℃，压力为常压，反应时间为4分钟。 (Z) -2-(2-戊烯基) -3-环戊烯-1-醇通过和1mol双氧水反应生成（Z） -2-（2-戊烯基）-2-环戊烯-1-酮，反应温度为55℃，压力为3个标准大气压，反应时间为18分钟；（Z）-2-（2-戊烯基）-2-环戊烯-1-酮通过和1mol甲基锂反应生成（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇，在氮气保护下进行；（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇通过和1mol氧化铬1mol盐酸反应生成(Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮，在负压下反应生成，负压为0.3个标准大气压。生成0.77mol(Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮。Take 1mol of cyclopentadiene and 1mol of ketene at a reaction temperature of 40-60 ° C, the pressure is normal pressure, and the reaction time is 40 minutes to generate 7,7-dichlorobicyclo(3.2.0) hept-2-ene- 6-keto; Bicyclo[3,2,0]hept-2-ene is generated by 7,7-dichlorobicyclo(3.2.0)hept-2-en-6-one substitution reaction with 2mol Zn and excess acetic acid -6-keto; in bicyclo[3,2,0]hept-2-en-6-one, 3,3a,4,6a tetrahydro-2H-cyclopentadieno[b was generated by reacting with excess acetic acid 1mol hydrogen peroxide ]furan-2-one, oxygen was continuously introduced during the reaction; 3,3a,4,6atetrahydro-2H-cyclopentadieno[b]furan-2-one was added to 2mol lithium hydride to generate 3 ,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-ol, the reaction process was carried out under nitrogen protection; 3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan -2-ol was reacted with 1 mol of triphenyl-ethylidene phosphine to generate (Z)-2-(2-pentenyl)-3-cyclopenten-1-ol. The reaction temperature was 55 °C and the pressure was normal pressure, and the reaction time was 4 minutes. (Z)-2-(2-pentenyl)-3-cyclopenten-1-ol was reacted with 1mol hydrogen peroxide to generate (Z)-2-(2-pentenyl)-2-cyclopenten-1 -ketone, the reaction temperature was 55°C, the pressure was 3 standard atmospheres, and the reaction time was 18 minutes; (Z)-2-(2-pentenyl)-2-cyclopenten-1-one was passed through and 1 mol methyl Lithium reacts to generate (Z)-1-methyl-2-(2-pentenyl)-2-cyclopenten-1-ol, which is carried out under nitrogen protection; (Z)-1-methyl-2-( 2-pentenyl)-2-cyclopenten-1-ol was reacted with 1 mol of chromium oxide and 1 mol of hydrochloric acid to generate (Z)-3-methyl-2-(2-pentenyl)-2-cyclopentene- The 1-ketone is formed by the reaction under negative pressure, and the negative pressure is 0.3 standard atmosphere. 0.77 mol of (Z)-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one was produced.
实施例3Example 3
取1mol环戊二烯和1mol乙烯酮在反应温度为60℃，压力为常压，反应时间为60分钟，生成7,7-二氯二环(3.2.0 )庚-2-烯-6-酮；通过7,7-二氯二环(3.2.0 )庚-2-烯-6-酮在和2molZn、过量醋酸发生取代反应生成双环[3,2,0]庚-2-烯-6-酮；在双环[3,2,0]庚-2-烯-6-酮通过和过量醋酸1mol双氧水反应生成3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮，反应过程中持续通入氧气；3,3a,4,6a四氢-2H-环戊二烯并[b]呋喃-2-酮通过和2mol氢化锂加成反应生成3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇，反应过程在氮气保护下进行；3,3a，6,6a-四氢-2H-环戊[b]呋喃-2-醇通过和1mol三苯基-亚乙基膦反应生成(Z) -2-(2-戊烯基) -3-环戊烯-1-醇，反应温度为60℃，压力为常压，反应时间为5分钟。 (Z) -2-(2-戊烯基) -3-环戊烯-1-醇通过和1mol双氧水反应生成（Z） -2-（2-戊烯基）-2-环戊烯-1-酮，反应温度为60℃，压力为3个标准大气压，反应时间为20分钟；（Z）-2-（2-戊烯基）-2-环戊烯-1-酮通过和1mol甲基锂反应生成（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇，在氮气保护下进行；（Z）-1-甲基-2-（2-戊烯基）-2-环戊烯-1-醇通过和1mol氧化铬1mol盐酸反应生成(Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮，在负压下反应生成，负压为0.3个标准大气压。生成0.81mol(Z)-3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮。Take 1 mol of cyclopentadiene and 1 mol of ketene at a reaction temperature of 60° C., a pressure of normal pressure, and a reaction time of 60 minutes to generate 7,7-dichlorobicyclo(3.2.0)hept-2-ene-6- Ketone; Bicyclo[3,2,0]hept-2-ene-6 is formed by substitution reaction of 7,7-dichlorobicyclo(3.2.0)hept-2-en-6-one with 2mol Zn and excess acetic acid -ketone; in bicyclo[3,2,0]hept-2-en-6-one, 3,3a,4,6a tetrahydro-2H-cyclopentadieno[b]furan was generated by reacting with excess acetic acid 1mol hydrogen peroxide -2-one, oxygen was continuously introduced during the reaction; 3,3a,4,6a tetrahydro-2H-cyclopentadieno[b]furan-2-one was added to 2mol lithium hydride to generate 3,3a , 6,6a-tetrahydro-2H-cyclopenta[b]furan-2-ol, the reaction process was carried out under nitrogen protection; 3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2 -The alcohol is reacted with 1mol triphenyl-ethylidene phosphine to generate (Z)-2-(2-pentenyl)-3-cyclopenten-1-ol, the reaction temperature is 60 ℃, the pressure is normal pressure, The reaction time was 5 minutes. (Z)-2-(2-pentenyl)-3-cyclopenten-1-ol was reacted with 1mol hydrogen peroxide to generate (Z)-2-(2-pentenyl)-2-cyclopenten-1 -ketone, the reaction temperature was 60 °C, the pressure was 3 standard atmospheres, and the reaction time was 20 minutes; (Z)-2-(2-pentenyl)-2-cyclopenten-1-one was passed through and 1 mol methyl Lithium reacts to generate (Z)-1-methyl-2-(2-pentenyl)-2-cyclopenten-1-ol, which is carried out under nitrogen protection; (Z)-1-methyl-2-( 2-pentenyl)-2-cyclopenten-1-ol was reacted with 1 mol of chromium oxide and 1 mol of hydrochloric acid to generate (Z)-3-methyl-2-(2-pentenyl)-2-cyclopentene- The 1-ketone is formed by the reaction under negative pressure, and the negative pressure is 0.3 standard atmosphere. 0.81 mol of (Z)-3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one was produced.
本发明至少具有以下优点：The present invention has at least the following advantages:
本发明方法合成路线清晰，不涉及到常规方法中的溴元素，且工艺难度及制备均低，有利于大规模生产应用。The method of the invention has a clear synthetic route, does not involve the bromine element in the conventional method, and has low technological difficulty and preparation, which is favorable for large-scale production and application.
以上所述仅是本发明的优选实施方式，并不用于限制本发明，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明技术原理的前提下，还可以做出若干改进和变型，这些改进和变型也应视为本发明的保护范围。The above are only the preferred embodiments of the present invention and are not intended to limit the present invention. It should be pointed out that for those skilled in the art, some improvements can be made without departing from the technical principles of the present invention. These improvements and modifications should also be regarded as the protection scope of the present invention.
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| US4045489A (en) * | 1976-01-15 | 1977-08-30 | International Flavors & Fragrances Inc. | Process for producing cis-jasmone |
| CN107573309A (en) * | 2016-07-04 | 2018-01-12 | 沈阳欧利康化学科技有限公司 | The preparation method of esterdiol in a kind of corey |
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| CN108546258A (en) * | 2018-04-10 | 2018-09-18 | 厦门欧瑞捷生物科技有限公司 | A kind of method that simple and effective synthesizes esterdiol in Corey |
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| US4045489A (en) * | 1976-01-15 | 1977-08-30 | International Flavors & Fragrances Inc. | Process for producing cis-jasmone |
| CN107573309A (en) * | 2016-07-04 | 2018-01-12 | 沈阳欧利康化学科技有限公司 | The preparation method of esterdiol in a kind of corey |
| CN107935823A (en) * | 2017-10-30 | 2018-04-20 | 江西盛伟科技股份有限公司 | The preparation method of cis-jasmone |
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