3-(5-phenyl-thiophen-2-yl)-acrylic acid ethyl ester | 923261-74-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(5-phenyl-thiophen-2-yl)-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-(5-phenylthiophen-2-yl)prop-2-enoate
• CAS: 923261-74-9
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: PMPPHAIHRYXNGZ-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-phenyl-thiophen-2-yl)-acrylic acid ethyl ester 在 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 反应 120.0h， 以27%的产率得到(+)-(2S,3S)-2,3-dihydroxy-3-(5-phenyl-thiophen-2-yl)-propionic acid ethyl ester
  参考文献：
  名称：

  Application of Sharpless asymmetric dihydroxylation to thienyl- and benzothienyl acrylates and crotonates

  摘要：

  Optimized conditions for the catalytic asymmetric dihydroxylation have been applied to thiophene and benzothiophene containing acrylates and crotonates to afford the corresponding diols in good overall yields and good to excellent enantiomeric excess. The products obtained were revealed to be useful intermediates in peptidomimetic synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.035
• 作为产物：
  描述：

  5-苯基-2-噻吩甲醛 、 磷酰基乙酸三乙酯 以 甲苯 为溶剂， 反应 16.0h， 以90%的产率得到3-(5-phenyl-thiophen-2-yl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Application of Sharpless asymmetric dihydroxylation to thienyl- and benzothienyl acrylates and crotonates

  摘要：

  Optimized conditions for the catalytic asymmetric dihydroxylation have been applied to thiophene and benzothiophene containing acrylates and crotonates to afford the corresponding diols in good overall yields and good to excellent enantiomeric excess. The products obtained were revealed to be useful intermediates in peptidomimetic synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.035

文献信息

• Application of Sharpless asymmetric dihydroxylation to thienyl- and benzothienyl acrylates and crotonates
  作者：Carlo Bonini、Lucia Chiummiento、Margherita De Bonis、Maria Funicello、Paolo Lupattelli、Rocco Pandolfo

  DOI：10.1016/j.tetasy.2006.10.035

  日期：2006.11

  Optimized conditions for the catalytic asymmetric dihydroxylation have been applied to thiophene and benzothiophene containing acrylates and crotonates to afford the corresponding diols in good overall yields and good to excellent enantiomeric excess. The products obtained were revealed to be useful intermediates in peptidomimetic synthesis. (c) 2006 Elsevier Ltd. All rights reserved.