Methyl 2β-ethoxy-3β-methyl-1β-(1(E)-propenyl)cyclopropane-1α-carboxylate | 140928-54-7

• 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: Methyl 2β-ethoxy-3β-methyl-1β-(1(E)-propenyl)cyclopropane-1α-carboxylate
• 英文别名: methyl (1R,2R,3R)-2-ethoxy-3-methyl-1-[(E)-prop-1-enyl]cyclopropane-1-carboxylate
• CAS: 140928-54-7
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: KQTJKRKOCBEOSH-VFIKGXQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2β-ethoxy-3β-methyl-1β-(1(E)-propenyl)cyclopropane-1α-carboxylate 在 氯化二乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以81%的产率得到Methyl (3β,4α,5α)-4-ethoxy-3,5-dimethylcyclopent-1-ene-1-carboxylate
  参考文献：
  名称：

  Highly stereoselective [3 + 2] annulations by cyclopropanation of vinyl ethers with rhodium(II)-stabilized vinylcarbenoids followed by a formally forbidden 1,3-sigmatropic rearrangement

  摘要：

  A highly stereoselective 3 + 2 annulation has been developed by cyclopropanation of vinyl ethers with rhodium(II)-stabilized vinylcarbenoids to generate vinylcyclopropanes followed by a Et2AlCl-catalyzed 1,3-sigmatropic rearrangement. The success of this methodology rests on the remarkably stereoselectivity that is exhibited in both the cyclopropanation step and also the Et2AlCl-catalyzed vinylcyclopropane rearrangement.

  DOI：

  10.1021/jo00037a041
• 作为产物：
  描述：

  乙基丙烯醚 、 methyl (E)-2-diazopent-3-enoate 在 rhodium(II) pivalate 作用下， 以 正戊烷 为溶剂， 以83%的产率得到Methyl 2β-ethoxy-3β-methyl-1β-(1(E)-propenyl)cyclopropane-1α-carboxylate
  参考文献：
  名称：

  Highly stereoselective [3 + 2] annulations by cyclopropanation of vinyl ethers with rhodium(II)-stabilized vinylcarbenoids followed by a formally forbidden 1,3-sigmatropic rearrangement

  摘要：

  A highly stereoselective 3 + 2 annulation has been developed by cyclopropanation of vinyl ethers with rhodium(II)-stabilized vinylcarbenoids to generate vinylcyclopropanes followed by a Et2AlCl-catalyzed 1,3-sigmatropic rearrangement. The success of this methodology rests on the remarkably stereoselectivity that is exhibited in both the cyclopropanation step and also the Et2AlCl-catalyzed vinylcyclopropane rearrangement.

  DOI：

  10.1021/jo00037a041

文献信息

• Highly stereoselective [3 + 2] annulations by cyclopropanation of vinyl ethers with rhodium(II)-stabilized vinylcarbenoids followed by a formally forbidden 1,3-sigmatropic rearrangement
  作者：Huw M. L. Davies、Baihua Hu

  DOI：10.1021/jo00037a041

  日期：1992.5

  A highly stereoselective 3 + 2 annulation has been developed by cyclopropanation of vinyl ethers with rhodium(II)-stabilized vinylcarbenoids to generate vinylcyclopropanes followed by a Et2AlCl-catalyzed 1,3-sigmatropic rearrangement. The success of this methodology rests on the remarkably stereoselectivity that is exhibited in both the cyclopropanation step and also the Et2AlCl-catalyzed vinylcyclopropane rearrangement.