(R)-(+)-1-(4'-chlorophenyl)propyl acetate | 444729-09-3

• 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: (R)-(+)-1-(4'-chlorophenyl)propyl acetate
• 英文别名: [(1R)-1-(4-chlorophenyl)propyl] acetate
• CAS: 444729-09-3
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: XDWKHOYVNAYRQX-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 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：

  (R)-(+)-1-(4'-chlorophenyl)propyl acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以91%的产率得到(alphaR)-4-氯-alpha-乙基苯甲醇
  参考文献：
  名称：

  Biocatalytically assisted preparation of antifungal chlorophenylpropanols

  摘要：

  Fermenting baker's yeast converts 4'-chloropropiophenone 1 and 3'-chloropropiophenone 2 into enantiopure (S)-(-)-1(4'-chlorophenyl)propan-1-ol (S)-3 and (S)-(+)-1-(3'-chlorophenyl)propan-1-ol (S)-4, respectively. Application of inhibitors and organic solvents as additives enhanced the enantiomeric excesses. Enantiopure compounds (R)-(+)-1-(4'-chlorophenyl)propan-1-of ((R)-3) and (R)-(+)-1-(3'-chlorophenyl)propan-1-ol (R)-4 were prepared by lipase-mediated esterifications of the racemic alcohols. Maximum inhibition of the growth of the phytopathougenic fungus Botrytis cinerea was shown for the (R)-enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00415-9
• 作为产物：
  描述：

  4-氯苯丙酮 在 sodium tetrahydroborate 、 lipase from Pseudomonas Cepacia 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 168.0h， 生成 (R)-(+)-1-(4'-chlorophenyl)propyl acetate
  参考文献：
  名称：

  Biocatalytically assisted preparation of antifungal chlorophenylpropanols

  摘要：

  Fermenting baker's yeast converts 4'-chloropropiophenone 1 and 3'-chloropropiophenone 2 into enantiopure (S)-(-)-1(4'-chlorophenyl)propan-1-ol (S)-3 and (S)-(+)-1-(3'-chlorophenyl)propan-1-ol (S)-4, respectively. Application of inhibitors and organic solvents as additives enhanced the enantiomeric excesses. Enantiopure compounds (R)-(+)-1-(4'-chlorophenyl)propan-1-of ((R)-3) and (R)-(+)-1-(3'-chlorophenyl)propan-1-ol (R)-4 were prepared by lipase-mediated esterifications of the racemic alcohols. Maximum inhibition of the growth of the phytopathougenic fungus Botrytis cinerea was shown for the (R)-enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00415-9

文献信息

• An Amino Alcohol Ligand for Highly Enantioselective Addition of Organozinc Reagents to Aldehydes:  Serendipity Rules
  作者：William A. Nugent

  DOI：10.1021/ol0259488

  日期：2002.6.1

  bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.

  [反应：见正文]氨基醇4（或其对映体）可通过两个简单步骤制备。用双（2-溴乙基）醚将商业（1R，2S）-2-氨基-1，2-二苯基乙醇二烷基化。随后在吗啉存在下于氧化铝上在Rh上进行超过5％Rh的氢化反应意外地在六氢衍生物4处停止。氨基醇4促进了室温下二乙基锌对醛的对映选择性加成，其对映体过量高达99％。
• Screening of liver acetone powders in the resolution of 1-phenylethanols and 1-phenylpropanols derivatives
  作者：Aida Solís、Susana García、Herminia I. Pérez、Norberto Manjarrez、Héctor Luna

  DOI：10.1016/j.tetasy.2008.01.041

  日期：2008.3

  Hydrolases from the liver acetone powders (LAPs) of bovine, cat, chicken, turkey, lamb, pig, rabbit, and rat were assessed for the enantioselective hydrolysis of acetates of 1-(4-chlorophenyl)ethanot, 1-(3-bromophenyl)ethanol, 1-(4-chlorophenyl)propanol, 1-(4-bromophenyl)propanol, and 1-(3-bromophenyl)propanol. The enantioselectivity of the hydrolytic reaction was dependent upon the liver hydrolase, substrate, pH of the reaction media, and the cosolvent. The most ester selective LAP was from chicken, and the resulting alcohols had the highest ee (80% to >99%). All of the LAPs tested catalyzed the hydrolysis of 1-(4-chlorophenyl)ethanol, except for lamb LAP. (C) 2008 Elsevier Ltd. All rights reserved.