S-ethyl (1R,2R)-2-(but-3-enyl)cyclopropanecarbothioate | 1251535-29-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: S-ethyl (1R,2R)-2-(but-3-enyl)cyclopropanecarbothioate
• CAS: 1251535-29-1
• 化学式: C₁₀H₁₆OS
• 分子量: 184.302
• InChiKey: UBJCUYGMYODODL-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 S-ethyl (1R,2R)-2-(but-3-enyl)cyclopropanecarbothioate 在 potassium carbonate 作用下， 反应 3.0h， 生成 methyl (R,R)-2-(but-3-enyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Copper-Catalyzed Enantioselective Synthesis of trans-1-Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Addition−Intramolecular Enolate Trapping

  摘要：

  Cu-TolBINAP-catalyzed conjugate addition of Grignard reagents to 4-chloro-alpha,beta-unsaturated esters, thioesters, and ketones leads to 4-chloro-3-alkyl-substituted thioesters and ketones in up to 84% yield and up to 96% ee upon protonation of the corresponding enolates at low temperature. Tandem conjugate addition-enolate trapping, however, yields trans-1-alkyl-2-substituted cyclopropanes in up to 92% yield and up to 98% ee. The versatility of this reaction is illustrated by the formation of key intermediates for the formal syntheses of cascarillic acid and grenadamide.

  DOI：

  10.1021/ja105704m
• 作为产物：
  描述：

  4-溴-1-丁烯 、 S-ethyl (E)-4-chlorobut-2-enethioate 在 magnesium 、 copper(l) iodide 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 作用下， 以 乙醚 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 6.0h， 以88%的产率得到S-ethyl (1R,2R)-2-(but-3-enyl)cyclopropanecarbothioate
  参考文献：
  名称：

  Copper-Catalyzed Enantioselective Synthesis of trans-1-Alkyl-2-substituted Cyclopropanes via Tandem Conjugate Addition−Intramolecular Enolate Trapping

  摘要：

  Cu-TolBINAP-catalyzed conjugate addition of Grignard reagents to 4-chloro-alpha,beta-unsaturated esters, thioesters, and ketones leads to 4-chloro-3-alkyl-substituted thioesters and ketones in up to 84% yield and up to 96% ee upon protonation of the corresponding enolates at low temperature. Tandem conjugate addition-enolate trapping, however, yields trans-1-alkyl-2-substituted cyclopropanes in up to 92% yield and up to 98% ee. The versatility of this reaction is illustrated by the formation of key intermediates for the formal syntheses of cascarillic acid and grenadamide.

  DOI：

  10.1021/ja105704m