Methyl 2β-methoxy-3β-(4-methoxyphenyl)-1β-((E)-2-phenylethenyl)cyclopropane-1α-carboxylate | 140928-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 2β-methoxy-3β-(4-methoxyphenyl)-1β-((E)-2-phenylethenyl)cyclopropane-1α-carboxylate
• 英文别名: methyl (1S,2S,3S)-2-methoxy-3-(4-methoxyphenyl)-1-[(E)-2-phenylethenyl]cyclopropane-1-carboxylate
• CAS: 140928-58-1
• 化学式: C₂₁H₂₂O₄
• 分子量: 338.403
• InChiKey: SATCVHRYHTZNOI-RMMZPDKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 2β-methoxy-3β-(4-methoxyphenyl)-1β-((E)-2-phenylethenyl)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61%的产率得到Methyl (3β,4α,5α)-4-methoxy-5-(4-methoxyphenyl)-3-phenylcyclopent-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：

  1-methoxy-4-(2-methoxyvinyl)benzene 、 (E)-methyl 2-diazo-4-phenylbut-3-enoate 在 rhodium(II) octanoate 作用下， 以 正戊烷 为溶剂， 以39%的产率得到Methyl 2β-methoxy-3β-(4-methoxyphenyl)-1β-((E)-2-phenylethenyl)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.