(S)-isopropyl 4-chloro-3-hydroxybutanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-isopropyl 4-chloro-3-hydroxybutanoate
• 英文别名: (S)-4-chloro-3-hydroxybutanoic acid isopropyl ester；isopropyl-(S)-4-chloro-3-hydroxybutyric acid；propan-2-yl (3S)-4-chloro-3-hydroxybutanoate
• 化学式: C₇H₁₃ClO₃
• 分子量: 180.631
• InChiKey: BZXNYWHUGJDAFS-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-isopropyl 4-chloro-3-hydroxybutanoate 在 吡啶 、 sodium azide 、 铑 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  一种(S)-奥拉西坦的制备方法

  摘要：

  一种(S)-奥拉西坦的制备方法，包括如下步骤：(1)以S-4-氯-3-羟基丁酸酯为起始原料，与叠氮化试剂进行叠氮化反应，得到中间体I；(2)将中间体I进行还原反应，获得中间体II；(2)将中间体II与卤代乙酸酯进行缩合反应，获得中间体Ⅲ；(3)将中间体Ⅲ进行关环反应得到中间体IV；(4)将中间体IV进行氨解反应，得到目标产物(S)-奥拉西坦。本发明至少可获得38%以上较理想收率的(S)-奥拉西坦产物，开辟了一条新的(S)-奥拉西坦合成路线。

  公开号：

  CN105330581A
• 作为产物：
  描述：

  i-propyl 4-chloro-3-hydroxybutyrate 生成 (S)-isopropyl 4-chloro-3-hydroxybutanoate
  参考文献：
  名称：

  A novel generation of optically active ethyl 4-chloro-3-hydroxybutyrate as a C4 chiral building unit using microbial dechlorination

  摘要：

  A novel procedure for the generation of optically active ethyl 4-chloro-3-hydroxybutyrate using bacterial cells was developed. Ethyl (S)-4-chloro-3-hydroxybutyrate was prepared by Pseudomonas sp. OS-K-29, which stereoselectively assimilates 2,3-dichloro-1-propanol. The reaction was based on its kinetic dehalogenation for both enantiomers using the resting cells. The obtained 4-chloro-3-hydroxybutyrate rate had high enantiomeric excess of >98%, with a yield of 33% at the microbial resolution step. Moreover, several C4 compounds having the 4-chloro-3-hydroxyl function were also resolved and gave good enantiomeric purities (>95 %ee). Ethyl (R)-4-chloro-3-hydroxybutyrate was also obtained with high enantiomeric purity (>98 %ee) using the cells of Pseudomonas sp DS-K-NR818. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00410-7

文献信息

• [EN] PROCESS FOR THE PREPARATION OF OPTICALLY PURE 4-HYDROXY-2-OXO-1-PYRROLIDINE ACETAMIDE<br/>[FR] PROCEDE DE PREPARATION D'ACETAMIDE DE 4-HYDROXY-2-OXO-1-PYRROLIDINE OPTIQUEMENT PUR
  申请人：AHN GOOK PHARMACEUTICAL CO LTD

  公开号：WO2005115978A1

  公开（公告）日：2005-12-08

  The present invention relates to a process for the preparation of chiral 4-hydroxy-2-oxo-1-pyrrolidine acetamide. The process comprises adding sodium cyanide together with citric acid to a solution of chiral epichlorohydrin to obtain chiral 3-chloro-2-hydroxypropionitrile by ring opening reaction of the chiral epichlorohydrin, reacting the obtained product with an alcohol containing hydrochloride gas to obtain chiral 4-chloro-3-hydroxybutyric acid ester, and reacting the obtained product in a presence of a base with glycinamide or with glycine ester accompanied by ammonolysis with ammonia to produce the targeted chiral 4-hydroxy-2-oxo-1-pyrrolidine acetamide. The process according to the present invention provides optically pure 4-hydroxy-2-oxo-1-pyrrolidine acetamide in high yield and in high purity, which is suitable for industrial mass-production.

  本发明涉及一种制备手性4-羟基-2-氧代-1-吡咯烷乙酰胺的工艺。该工艺包括将氰化钠与柠檬酸一起加入手性环氧氯丙烷的溶液中，通过环氧氯丙烷的开环反应得到手性3-氯-2-羟基丙腈，将所得产物与含有盐酸气体的醇反应得到手性4-氯-3-羟基丁酸酯，然后在碱存在下将所得产物与甘氨酰胺或甘氨酯伴随氨气的氨解反应得到目标手性4-羟基-2-氧代-1-吡咯烷乙酰胺。本发明的工艺能够高产高纯度地提供光学纯的4-羟基-2-氧代-1-吡咯烷乙酰胺，适用于工业大规模生产。
• Chemoenzymatic Dynamic Kinetic Resolution of β-Halo Alcohols. An Efficient Route to Chiral Epoxides
  作者：Oscar Pàmies、Jan-E. Bäckvall

  DOI：10.1021/jo026157m

  日期：2002.12.1

  Enzymatic resolution of beta-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when beta-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation

  β-氯醇的酶促拆分与钌催化的醇异构化相结合，成功实现了动态动力学拆分（转化率高达99％，ee高达97％）。当使用β-溴醇时，DKR的效率会大大降低。溴取代基的存在会导致钌催化剂分解，从而触发酶的逐步失活。该方法的合成效用已通过不同手性环氧化物的实际合成得到说明。
• Process for producing ß-hydroxyester
  申请人：Igi Kimitaka

  公开号：US20060122419A1

  公开（公告）日：2006-06-08

  A process for producing a β-hydroxyester by reacting an epoxide, an alcohol and carbon monoxide in the presence of a cobalt carbonyl compound as catalyst, which is characterized in using as co-catalyst, a pyridine derivative having an amino substituent of formula (1), wherein R 1 and R 2 are independently hydrogen, formyl, acyl, alkoxycarbonyl, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or R 1 and R 2 may be taken together with the adjacent nitrogen atom to form a ring, and n is an integer of 1 or 2.

  一种生产β-羟基酯的方法，包括在钴羰基化合物的催化下，通过反应环氧化物、醇和一氧化碳来实现，其特征在于使用一种具有式（1）中氨基取代基的吡啶衍生物作为共催化剂，其中R1和R2独立地是氢、甲酰、酰基、烷氧基羰基、取代或未取代的烷基、取代或未取代的芳基烷基、取代或未取代的芳基，或R1和R2可以与相邻的氮原子一起形成环，n是1或2的整数。
• Process for producing β-hydroxyester
  申请人：Daiso Co., Ltd.

  公开号：US07256305B2

  公开（公告）日：2007-08-14

  A process for producing a β-hydroxyester by reacting an epoxide, an alcohol and carbon monoxide in the presence of a cobalt carbonyl compound as catalyst, which is characterized in using as co-catalyst, a pyridine derivative having an amino substituent of formula (1), wherein R1 and R2 are independently hydrogen, formyl, acyl, alkoxycarbonyl, substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, or R1 and R2 may be taken together with the adjacent nitrogen atom to form a ring, and n is an integer of 1 or 2.

  一种生产β-羟酸酯的方法，通过在钴羰基化合物的催化下，反应环氧化物、醇和一氧化碳，并以具有式（1）中的含氨基取代基的吡啶衍生物作为辅助催化剂，其中R1和R2独立地为氢、甲酰基、酰基、烷氧基羰基、取代或未取代的烷基、取代或未取代的芳基烷基、取代或未取代的芳基，或R1和R2可以与相邻的氮原子结合形成环，n为1或2的整数。
• One-Way Biohydrogen Transfer for Oxidation of <i>sec</i>-Alcohols
  作者：Iván Lavandera、Alexander Kern、Verena Resch、Bianca Ferreira-Silva、Anton Glieder、Walter M. F. Fabian、Stefaan de Wildeman、Wolfgang Kroutil

  DOI：10.1021/ol800549f

  日期：2008.6.5

  Quasi-irreversible oxidation of sec4cohols was achieved via biocatalytic hydrogen transfer reactions using alcohol dehydrogenases employing selected ketones as hydrogen acceptors, which can only be reduced but not oxidized. Thus, only 1 equiv of oxidant was required instead of a large excess. For the oxidation of both isomers of methylcarbinols a single nonstereoselective short-chain dehydrogenase/reductase from Sphingobium yanoikuyae was identified and overexpressed in E. coli.