i-propyl 4-chloro-3-hydroxybutyrate | 89693-37-8

• 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: i-propyl 4-chloro-3-hydroxybutyrate
• 英文别名: (+/-)-isopropyl 4-chloro-3-hydroxybutanoate；propan-2-yl 4-chloro-3-hydroxybutyrate；γ-Chlor-β-hydroxy-buttersaeure-isopropylester；Propan-2-yl 4-chloro-3-hydroxybutanoate
• CAS: 89693-37-8
• 化学式: C₇H₁₃ClO₃
• 分子量: 180.631
• InChiKey: BZXNYWHUGJDAFS-UHFFFAOYSA-N

物化性质

• 沸点：
  108-110 °C(Press: 12 Torr)
• 密度：
  1.148±0.06 g/cm3(Predicted)

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：

  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
• 作为产物：
  描述：

  4-氯-3-氧代丁酸异丙酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 i-propyl 4-chloro-3-hydroxybutyrate
  参考文献：
  名称：

  One-Way Biohydrogen Transfer for Oxidation of sec-Alcohols

  摘要：

  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.

  DOI：

  10.1021/ol800549f

文献信息

• An Algorithm for the Deconvolution of Mass Spectrosopic Patterns in Isotope Labeling Studies. Evaluation for the Hydrogen−Deuterium Exchange Reaction in Ketones
  作者：Christian C. Gruber、Gustav Oberdorfer、Constance V. Voss、Jennifer M. Kremsner、C. Oliver Kappe、Wolfgang Kroutil

  DOI：10.1021/jo070831o

  日期：2007.7.1

  180 °C within 40−200 min. Compared to reflux conditions, the microwave-assisted protocol led to a reduction of the required reaction time from 75−94 h to 40−200 min. The α-labeled deuterium ketones were reduced by biocatalytic hydrogen transfer to the corresponding enantiopure chiral alcohols and the deconvolution algorithm validated by regression analysis of a mixture of labeled and unlabeled ketones/alcohols

  描述和评估了一种易于使用的计算机化算法，用于根据质谱数据确定每种标记物质的数量，这些物质的掺入同位素标记物的数量不同。使用该算法，在时间、温度和标记程度方面优化了通过氢-氘交换与氧化氘交换各种 α 标记的氘酮的微波辅助合成。对于热稳定的酮，α-质子的交换是在 180 °C 下在 40-200 分钟内实现的。与回流条件相比，微波辅助方案将所需的反应时间从 75-94 小时减少到 40-200 分钟。
• [DE] VERFAHREN ZUR HERSTELLUNG VON 4-CYANO-3-HYDROXYBUTTERSÄUREESTERN<br/>[EN] METHOD FOR PRODUCING 4-CYANO-3-HYDROXYBUTYRIC ACID ESTERS<br/>[FR] PROCEDE POUR PRODUIRE DES ESTERS DE L'ACIDE 4-CYANO-3-HYDROXYBUTYRIQUE
  申请人：BAYER CHEMICALS AG

  公开号：WO2005005375A1

  公开（公告）日：2005-01-20

  Bereitgestellt wird ein Verfahren zur Herstellung von 4-Cyano- 3-hydroxybuttersäureestem durch Umsetzung eines 4-­substituierten 3-Hydroxybuttersäureesters mit einern Cyanidsalz in einern organischen Lösungsmittel in Gegenwart eines oder mehrerer weiterer Salze.

  提供一种通过在有机溶剂中将4-取代的3-羟基丁酸酯与氰化盐反应，在一个或多个其他盐的存在下制备4-氰基-3-羟基丁酸酯的方法。
• 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。
• 一种奥拉西坦的制备方法
  申请人：重庆东泽医药科技发展有限公司

  公开号：CN105439936A

  公开（公告）日：2016-03-30

  一种奥拉西坦的制备方法，包括如下步骤：(1)以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，得到目标产物奥拉西坦。本发明至少可获得38%以上较理想收率的奥拉西坦产物，开辟了一条新的奥拉西坦合成路线。
• 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。