ethyl 2-(2,4-bis(hydroxymethyl)-5-(thiophen-2-yl)cyclopent-1-en-1-yl)acetate | 1394173-78-4

• 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: ethyl 2-(2,4-bis(hydroxymethyl)-5-(thiophen-2-yl)cyclopent-1-en-1-yl)acetate
• 英文别名: ethyl 2-[(4R,5R)-2,4-bis(hydroxymethyl)-5-thiophen-2-ylcyclopenten-1-yl]acetate
• CAS: 1394173-78-4
• 化学式: C₁₅H₂₀O₄S
• 分子量: 296.387
• InChiKey: TZMQZDWAESWXPN-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 ethyl 2-(2,4-bis(hydroxymethyl)-5-(thiophen-2-yl)cyclopent-1-en-1-yl)acetate 、 ethyl 2-(2,4-bis(hydroxymethyl)-5-(thiophen-2-yl)cyclopent-1-en-1-yl)acetate
  参考文献：
  名称：

  The combination of domino process and kinetic resolution: organocatalytic synthesis of functionalised cyclopentenes by sequential SN2′-Michael reaction

  摘要：

  An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S(N)2'-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee). (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2012.06.085