(S)-ethyl 2-methylcycloprop-2-ene-1-carboxylate | 221100-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-ethyl 2-methylcycloprop-2-ene-1-carboxylate
• 英文别名: ethyl (1S)-2-[[bis(2-trimethylsilylethoxycarbonyl)amino]methyl]cycloprop-2-ene-1-carboxylate
• CAS: 221100-99-8
• 化学式: C₁₉H₃₅NO₆Si₂
• 分子量: 429.661
• InChiKey: JGBYOTZRCMORDY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 2-methylcycloprop-2-ene-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以50%的产率得到乙基(1S)-2-(氨基甲基)-2-环丙烯-1-羧酸酯
  参考文献：
  名称：

  Rh(II)-catalyzed asymmetric cyclopropenation of propargyl derivatives; synthesis of cyclopropene- and cis-cyclopropane-amino acids

  摘要：

  The [Rh-2(2S)-mepy}(4)]-catalyzed cyclopropenation of propargylamines carrying two carboxyl or sulfonyl protecting groups with ethyl diazoacetate proceeds in high yield and with enantioselectivities in the range of 90->97% ee. Selective deprotection of the TEOC-derivative afforded ethyl 2-aminomethylcycloprop-2-ene-1-carboxylate which was converted to several analogs of gamma-aminobutyric acid (GABA) containing the cyclopropene or cyclopropane ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00469-8
• 作为产物：
  描述：

  prop-2-ynylcarbamic acid 2-trimethylsilylethyl ester 在 Doyle dirhodium catalyst 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (S)-ethyl 2-methylcycloprop-2-ene-1-carboxylate
  参考文献：
  名称：

  Rh(II)-catalyzed asymmetric cyclopropenation of propargyl derivatives; synthesis of cyclopropene- and cis-cyclopropane-amino acids

  摘要：

  The [Rh-2(2S)-mepy}(4)]-catalyzed cyclopropenation of propargylamines carrying two carboxyl or sulfonyl protecting groups with ethyl diazoacetate proceeds in high yield and with enantioselectivities in the range of 90->97% ee. Selective deprotection of the TEOC-derivative afforded ethyl 2-aminomethylcycloprop-2-ene-1-carboxylate which was converted to several analogs of gamma-aminobutyric acid (GABA) containing the cyclopropene or cyclopropane ring. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00469-8

文献信息

• Rh(II)-catalyzed asymmetric cyclopropenation of propargyl derivatives; synthesis of cyclopropene- and cis-cyclopropane-amino acids
  作者：Paul Müller、Hassan Imogaı̈

  DOI：10.1016/s0957-4166(98)00469-8

  日期：1998.12

  The [Rh-2(2S)-mepy}(4)]-catalyzed cyclopropenation of propargylamines carrying two carboxyl or sulfonyl protecting groups with ethyl diazoacetate proceeds in high yield and with enantioselectivities in the range of 90->97% ee. Selective deprotection of the TEOC-derivative afforded ethyl 2-aminomethylcycloprop-2-ene-1-carboxylate which was converted to several analogs of gamma-aminobutyric acid (GABA) containing the cyclopropene or cyclopropane ring. (C) 1998 Elsevier Science Ltd. All rights reserved.