(R)-2-butanoyl-1-phenylmethyl-3-chloro-1,2-propanediol | 151715-97-8

• 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)-2-butanoyl-1-phenylmethyl-3-chloro-1,2-propanediol
• 英文别名: [(2R)-1-chloro-3-phenylmethoxypropan-2-yl] butanoate
• CAS: 151715-97-8
• 化学式: C₁₄H₁₉ClO₃
• 分子量: 270.756
• InChiKey: IWRYYDAUGRXIGU-ZDUSSCGKSA-N

物化性质

• 沸点：
  372.3±27.0 °C(predicted)
• 密度：
  1.114±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-butanoyl-1-phenylmethyl-3-chloro-1,2-propanediol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (S)-苄氧甲基环氧乙烷
  参考文献：
  名称：

  Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol

  摘要：

  The enzymatic hydrolysis of butanoic esters of 1-phenylmethyl- and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol has been studied by using lipases. Highest enantiomeric ratio was obtained with PPL for the phenylmethyl ether and with Amano SAM II for the phenylethyl ether. The absolute configurations of the products were verified in two ways. Both the produced alcohols and the remaining esters were converted into the corresponding glycidyl ethers which also were synthesised in homochiral forms starting from (S)- epichlorohydrin. The produced alcohols and the remaining esters were prepared independently from (S)-epichlorohydrin.

  DOI：

  10.1016/s0957-4166(00)80140-8
• 作为产物：
  描述：

  苄基缩水甘油醚 在 dilithium tetrachlorocuprate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 60.0h， 生成 (R)-2-butanoyl-1-phenylmethyl-3-chloro-1,2-propanediol
  参考文献：
  名称：

  Organic co-solvents restore the inherently high enantiomeric ratio of lipase B from Candida antarctica in hydrolytic resolution by relieving the enantiospecific inhibition of product alcohol

  摘要：

  The enantiomeric ratio in the hydrolysis of racemic 3-chloro-1-phenylmethoxy-2-propyl butanoate with lipase B from Candida antarctica, CALB, is raised from E=50 to E=180 upon addition of acetone to the aqueous medium. This co-solvent effect is now explained as an enantiospecific inhibition of the lipase by the liberated alcohol. In the range from 0 to 30% acetone, the effect correlates with the increased solubility of the alcohol in the reaction medium. Free and immobilized CALB show similar behaviour. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00273-0

文献信息

• Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol
  作者：Vassilia Partali、Viggo Waagen、Thor Alvik、Thorleif Anthonsen

  DOI：10.1016/s0957-4166(00)80140-8

  日期：1993.5

  The enzymatic hydrolysis of butanoic esters of 1-phenylmethyl- and 1-[2-phenylethyl] ethers of 3-chloro-1,2-propanediol has been studied by using lipases. Highest enantiomeric ratio was obtained with PPL for the phenylmethyl ether and with Amano SAM II for the phenylethyl ether. The absolute configurations of the products were verified in two ways. Both the produced alcohols and the remaining esters were converted into the corresponding glycidyl ethers which also were synthesised in homochiral forms starting from (S)- epichlorohydrin. The produced alcohols and the remaining esters were prepared independently from (S)-epichlorohydrin.
• Co-solvent enhancement of enantioselectivity in lipase-catalysed hydrolysis of racemic esters. A process for production of homochiral C-3 building blocks using lipase B from Candida antarctica
  作者：Trond Vidar Hansen、Viggo Waagen、Vassilia Partali、Henrik W Anthonsen、Thorleif Anthonsen

  DOI：10.1016/0957-4166(95)00033-l

  日期：1995.2

  Lipase-catalysed hydrolysis of butanoates of 3-methoxy-1-(phenylmethoxy)-2-propanol and 3-chloro-1-(phenylmethoxy)-2-propanol with various lipases gave low enantioselectivity, E. By additon of water miscible organic cosolvents, in particular tert-butanol and acetone, the E-value was raised from 7 to 220 for the useful chloro derivative. This finding has led to proposal of a process for production of homochiral C-3 synthons such as both enantiomers of phenylmethyl glycidyl ether starting from racemic epichlorohydrin. NMR studies of lipase B from Candida antarctica show that the conformation most likely is not changed upon addition of up to 50% acetone. Nuclear Overhauser effects were observed upon irradiation of the phenyl protons of the substrate only in the presence of enzyme thus indicating an interaction between the two.
• Organic co-solvents restore the inherently high enantiomeric ratio of lipase B from Candida antarctica in hydrolytic resolution by relieving the enantiospecific inhibition of product alcohol
  作者：Kamilla Lundhaug、P.L.Antoine Overbeeke、Jaap A. Jongejan、Thorleif Anthonsen

  DOI：10.1016/s0957-4166(98)00273-0

  日期：1998.8

  The enantiomeric ratio in the hydrolysis of racemic 3-chloro-1-phenylmethoxy-2-propyl butanoate with lipase B from Candida antarctica, CALB, is raised from E=50 to E=180 upon addition of acetone to the aqueous medium. This co-solvent effect is now explained as an enantiospecific inhibition of the lipase by the liberated alcohol. In the range from 0 to 30% acetone, the effect correlates with the increased solubility of the alcohol in the reaction medium. Free and immobilized CALB show similar behaviour. (C) 1998 Elsevier Science Ltd. All rights reserved.