(S)-1-benzoyloxy-4-phenyl-E-3-butene-2-ol | 206257-91-2

• 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: (S)-1-benzoyloxy-4-phenyl-E-3-butene-2-ol
• 英文别名: [(E,2S)-2-hydroxy-4-phenylbut-3-enyl] benzoate
• CAS: 206257-91-2
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: UVRCSXLYRGDBTC-PCUGXKRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 、 (S)-1-benzoyloxy-4-phenyl-E-3-butene-2-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以73%的产率得到(S)-1-benzoyloxy-4-phenyl-E-3-butene-2-yl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2
• 作为产物：
  描述：

  Benzoic acid (E)-(S)-2-acetoxy-4-phenyl-but-3-enyl ester 在 吡啶 、 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 26.5h， 生成 (S)-1-benzoyloxy-4-phenyl-E-3-butene-2-ol
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2

文献信息

• Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof
  作者：Thomas Ziegler、Frank Bien、Claus Jurisch

  DOI：10.1016/s0957-4166(98)00051-2

  日期：1998.3

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.