(4-formyl-5-furan-2-yl-tetrahydro-thiophen-3-yl)-acetic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (4-formyl-5-furan-2-yl-tetrahydro-thiophen-3-yl)-acetic acid ethyl ester
• 英文别名: ethyl 2-[(3S,4R,5S)-4-formyl-5-(furan-2-yl)thiolan-3-yl]acetate
• 化学式: C₁₃H₁₆O₄S
• 分子量: 268.334
• InChiKey: MXCKBVVEYSSKNP-NRUUGDAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 、 trans-ethyl 4-mercapto-2-butenoate 在 (S)-diphenyl prolinol TMS ether 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以88%的产率得到(4-formyl-5-furan-2-yl-tetrahydro-thiophen-3-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Enantioselective Organocatalytic Double Michael Addition Reactions

  摘要：

  [GRAPHICS]A novel organocatalytic, enantioselective domino double Michael addition reaction of alpha,beta-unsaturated aldehydes with ethyl 4-mercapto-2-butenoate has been developed. The process is promoted by chiral diphenylprolinol TMS ether to give chiral tetrahydrothiophenes in high to excellent levels of enantioselectivities.

  DOI：

  10.1021/ol070581y

文献信息

• Enantioselective Organocatalytic Double Michael Addition Reactions
  作者：Hao Li、Liansuo Zu、Hexin Xie、Jian Wang、Wei Jiang、Wei Wang

  DOI：10.1021/ol070581y

  日期：2007.4.1

  [GRAPHICS]A novel organocatalytic, enantioselective domino double Michael addition reaction of alpha,beta-unsaturated aldehydes with ethyl 4-mercapto-2-butenoate has been developed. The process is promoted by chiral diphenylprolinol TMS ether to give chiral tetrahydrothiophenes in high to excellent levels of enantioselectivities.