1-phenylethyl caproate

• 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: 1-phenylethyl caproate
• 英文别名: [(1S)-1-phenylethyl] hexanoate
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XDNXTDFSRYCZFT-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苏合香醇 、 p-chlorophenyl hexanoate 在 Novozyme 435 lipase 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以99%的产率得到1-phenylethyl caproate
  参考文献：
  名称：

  Dynamic kinetic resolution of secondary aromatic alcohols with new efficient acyl donors

  摘要：

  A new and efficient dynamic kinetic resolution (DKR) process of secondary aromatic alcohols by using long carbon-chain esters as acyl donors has been developed. During the process, the transesterification catalyzed by CD8604 was found to be the main reason for the decrease in enantiomeric excess (ee). Using complex acyl donors, such as 4-chlorophenyl valerate, we could effectively inhibit the resin-catalyzed transesterification, and an excellent ee value (>99%) at high yield (>99%) was achieved. The mechanism for the inhibition of resin-catalyzed transesterification is believed to be the formation of micro-micelles in the pores of CD8604. It is noteworthy that the system can be reused more than 20 times without a loss of yield or ee value. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.034

文献信息

• Low-temperature enzymatic hydrolysis resolution in mini-emulsion media
  作者：Nuno M. T. Lourenço、Sara C. Matias、Margarida C. Altas、Luis P. Fonseca

  DOI：10.1515/chempap-2015-0032

  日期：2015.1.1

  mini-emulsion size was observed. For the longer 1-phenylethyl ester, 1-phenylethyl dodecanoate, the enzymatic resolution was promoted exclusively at low temperatures. The preparative mini-emulsion enzymatic reaction of 1-phenylethyl dodecanoate at 4 °C afforded the isolation of (R)-phenylethanol with a yield of 36 % with an ee of 99 %. (S)-Phenylethanol was isolated with a 51 % yield with an ee of 79 %.

  首次描述了一种用于酶解1-苯基乙醇的低温微乳液介质。在小乳液介质中，在南极假丝酵母脂肪酶B存在下，具有不同链长的1-苯基乙基酯的酶促水解拆分显示受温度显着控制。在该系统中，观察到温度对微乳液尺寸的直接影响。对于更长的1-苯基乙基酯，即十二烷基1-苯基乙基酯，仅在低温下才提高了酶促分离度。1-苯基乙基十二烷酸酯在4°C的制备型微乳液酶促反应可分离出（R）-苯基乙醇，收率为36％，ee为99％。（S分离出苯基乙醇，产率为51％，ee为79％。