(RS)-3-chloro-1-phenyl-1-propyl acetate | 22912-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-3-chloro-1-phenyl-1-propyl acetate
• 英文别名: 3-chloro-1-phenylpropyl acetate；acetic acid-(3-chloro-1-phenyl-propyl ester)；Essigsaeure-(3-chlor-1-phenyl-propylester)；(3-Chloro-1-phenylpropyl) acetate
• CAS: 22912-90-9
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: SHDPVMVSKQDBGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (RS)-3-chloro-1-phenyl-1-propyl acetate 在 Bacillus subtilis esterase 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (S)-(-)-3-氯-1-苯基-1-丙醇 、 (R)-(+)-3-氯-1-苯基-1-丙醇 、 (S)-3-chloro-1-phenyl-1-propyl acetate 、 (R)-3-chloro-1-phenylpropyl acetate
  参考文献：
  名称：

  从新分离的枯草芽孢杆菌ECU0554通过高底物浓度可耐受的酯酶酶促生产1-薄荷醇

  摘要：

  Abstractmagnified imageEnzymatic preparation of l‐menthol has been attracting much attention in the flavor and fragrance industry. A new ideal strain, Bacillus subtilis ECU0554, which exhibited high hydrolytic activity and excellent enantioselectivity towards l‐menthyl ester, has been successfully isolated from soil samples through enrichment culture and identified as Bacillus subtilis by 16S rDNA gene sequencing. The esterase extracted from B. subtilis ECU0554 (BSE) showed the best catalytic properties (E>200) for dl‐menthyl acetate among the five menthyl esters examined. Enantioselective hydrolysis of 100 mM dl‐menthyl acetate at 30°C and pH 7.0, using crude BSE as biocatalyst and 10% ethanol (v/v) as cosolvent, resulted in 49.0% conversion (3 h) and 98.0% ee for the l‐menthol produced, which were much better than those using commercial enzymes tested. Moreover, BSE exhibited strong tolerance against high substrate concentration (up to 500 mM), and the concentration of l‐menthol produced could reach as high as 182 mM, and more importantly, the optical purity of l‐menthol produced was kept above 97% ee, which were not found in previous reports. These results imply that BSE is a potentially promising biocatalyst for the large‐scale enzymatic preparation of l‐menthol. Using this excellent biocatalyst, the enzymatic production of l‐menthol will become a mild, efficient, inexpensive and easy‐to‐use “green chemistry” methodology.

  DOI：

  10.1002/adsc.200800412
• 作为产物：
  描述：

  3-氯-1-苯基丙醇 、 乙酸酐 在 五氯化钽 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到(RS)-3-chloro-1-phenyl-1-propyl acetate
  参考文献：
  名称：

  TaCl 5催化的乙酸酐对醇的酰化反应：动力学拆分的一些意义

  摘要：

  TaCl 5和TaCl 5-硅胶已经有效地用作路易斯酸催化剂用于醇的乙酰化。TaCl 5-手性配体也已经用于2°醇的动力学拆分，即使在低ee中也是如此。

  DOI：

  10.1016/s0040-4039(98)00465-1

文献信息

• Lipase-Catalyzed Synthesis of Both Enantiomers of 3-Chloro-1-arylpropan-1-ols
  作者：Florin-Dan Irimie、Laura Pop、Andrea Czompa、Csaba Paizs、Monica Toşa、Elemér Vass、Péter Mátyus

  DOI：10.1055/s-0030-1260149

  日期：2011.9

  3-chloro-1-(4-iodophenyl)propan-1-ol, and 3-chloro-1-phenylpropan-1-ol is described. The procedure is based on the enantiomer-selective acylation of the racemic alcohols in presence of lipase from Pseudomonas fluorescens (LAK) followed by the lipase from Candida rugosa (CRL) mediated hydrolysis of previously obtained enantiomerically enriched 1-aryl-3-chloropropyl esters. For the production of enantiopure (S)-1-ar

  脂肪酶催化3-氯-1-（4-氟苯基）丙-1-醇，3-氯-1-（4-碘苯基）丙-1-醇和3-氯-1-醇的两种对映体的合成描述了苯基丙-1-醇。该方法是基于在荧光假单胞菌（LAK）的脂肪酶存在下外消旋醇的对映异构体选择性酰化，然后是来自假丝酵母（CRL）的脂肪酶介导的先前获得的对映异构体富集的1-芳基-3-氯丙基酯的水解。对于生产对映纯（S）-1-芳基-3-氯丙烷-1-醇（99％ee，收率34-42％），以高于理论最佳50％的转化率停止反应，而对映纯（[R）-1-芳基-3-氯丙基乙酸酯（99％ee）以较低的转化率停止反应。将后面的化合物酶水解为相应的（R）-1-芳基-3-氯丙烷-1-醇（97-99％ee，18-24％收率）。分辨率产品的绝对配置是通过VCD测量结合量子化学计算来确定的。 酶-动力学拆分-对映选择性-手性拆分-醇类-卤化物
• PROCESS FOR PRODUCING OPTICALLY ACTIVE 3-CHLORO-1-PHENYL-1-PROPANOL AND DERIVATIVE THEREOF
  申请人：DAICEL CHEMICAL INDUSTRIES, LTD.

  公开号：EP0529085A1

  公开（公告）日：1993-03-03

  An industrially highly advantageous process for producing optically active substances with a high optical purity conveniently, which comprises treating an enantiomeric mixture of 3-chloro-1-(substituted)-phenyl-1-propyl esters of a saturated or unsaturated fatty acid with an enzyme which can asymmetrically hydrolyze the mixture, such as a lipase originating in the microorganism belonging to the genus Pseudomonas, Aspergillus, Candida or Chromobacterium to give a mixture containing optically 3-chloro-1-(substituted)-phenyl-1-propanol and optically active 3-chloro-1-(substituted)-phenyl-1-propyl ester of a saturated or unsaturated fatty acid, and separately recovering the optically active propanol or its derivative and the optically active propyl ester or its derivative from the mixture.

  一种方便地生产光学纯度高的光学活性物质的极具工业优势的工艺，包括用一种能不对称地水解该混合物的酶，如源自假单胞菌属微生物的脂肪酶，来处理饱和或不饱和脂肪酸的3-氯-1-（取代）-苯基-1-丙酯的对映体混合物，从而得到含有光学活性的3-氯-1-（取代）-苯基-1-丙醇和光学活性的3-氯-1-（取代）-苯基-1-丙醇的混合物、曲霉属、念珠菌属或色杆菌属的微生物的脂肪酶，以得到含有光学活性 3-氯-1-(取代)-苯基-1-丙醇和光学活性 3-氯-1-(取代)-苯基-1-丙基饱和或不饱和脂肪酸酯的混合物，并从混合物中分别回收光学活性丙醇或其衍生物和光学活性丙酯或其衍生物。
• Oxetanes. VI.¹ Reductive Cleavage and Substituent Effects²
  作者：Scott Searles、Kenneth A. Pollart、Eugene F. Lutz

  DOI：10.1021/ja01561a046

  日期：1957.2
• US5457052A
  申请人：——

  公开号：US5457052A

  公开（公告）日：1995-10-10
• Acylation of alcohols with acetic anhydride catalyzed by TaCl5: Some implications in kinetic resolution
  作者：S. Chandrasekhar、T. Ramachander、Mohamed Takhi

  DOI：10.1016/s0040-4039(98)00465-1

  日期：1998.5

  TaCl5 and TaCl5-Silica gel have been effectively used as Lewis acid catalysts for acetylation of alcohols. Also TaCl5-Chiral ligands have been used for kinetic resolution of 2° alcohols albeit in low ees.

  TaCl 5和TaCl 5-硅胶已经有效地用作路易斯酸催化剂用于醇的乙酰化。TaCl 5-手性配体也已经用于2°醇的动力学拆分，即使在低ee中也是如此。