(2S)-2-[4-[[(1R)-2-oxocyclohexyl]methyl]phenyl]propanoic acid | 1333080-47-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-2-[4-[[(1R)-2-oxocyclohexyl]methyl]phenyl]propanoic acid
• CAS: 1333080-47-9
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: JLGLDJKSKWKYNN-SMDDNHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[4-[[(1R)-2-oxocyclohexyl]methyl]phenyl]propanoic acid 在 Torulaspora delbrueckii NBRC 10921 作用下， 以 乙醇 为溶剂， 以72%的产率得到(S)-2-[4-((1R)-2-hydroxycyclohexylmethyl)phenyl]propionic acid
  参考文献：
  名称：

  Asymmetric synthesis of the active form of loxoprofen and its analogue

  摘要：

  The asymmetric synthesis of the active form of the antiinflammatory drug loxoprofen has been reported in this article. Enzymatic kinetic resolution/racemization of a substituted homo-benzylic primary alcohol with lipase-PS, asymmetric alkylation of cyclic ketones using either Enders' or Meyers' strategy followed by a stereoselective biocatalytic reduction of carbonyl group are the key reactions employed successfully to achieve the target molecule and one of its analogue. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.019
• 作为产物：
  描述：

  对苯二甲醇 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 重铬酸吡啶 、 草酰氯 、 dimethyl sulfide borane 、 Burkholderia cepacia lipase-PS 、 potassium tert-butylate 、 四丁基氟化铵 、 水 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 异丙醚 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 49.75h， 生成 (2S)-2-[4-[[(1R)-2-oxocyclohexyl]methyl]phenyl]propanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of the active form of loxoprofen and its analogue

  摘要：

  The asymmetric synthesis of the active form of the antiinflammatory drug loxoprofen has been reported in this article. Enzymatic kinetic resolution/racemization of a substituted homo-benzylic primary alcohol with lipase-PS, asymmetric alkylation of cyclic ketones using either Enders' or Meyers' strategy followed by a stereoselective biocatalytic reduction of carbonyl group are the key reactions employed successfully to achieve the target molecule and one of its analogue. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.019

文献信息

• Asymmetric synthesis of the active form of loxoprofen and its analogue
  作者：Rajib Bhuniya、Samik Nanda

  DOI：10.1016/j.tetasy.2011.06.019

  日期：2011.5

  The asymmetric synthesis of the active form of the antiinflammatory drug loxoprofen has been reported in this article. Enzymatic kinetic resolution/racemization of a substituted homo-benzylic primary alcohol with lipase-PS, asymmetric alkylation of cyclic ketones using either Enders' or Meyers' strategy followed by a stereoselective biocatalytic reduction of carbonyl group are the key reactions employed successfully to achieve the target molecule and one of its analogue. (C) 2011 Elsevier Ltd. All rights reserved.