Methyl 2β-ethoxy-3β-methyl-1β-((E)-2-phenylethenyl)cyclopropane-1α-carboxylate | 140928-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2β-ethoxy-3β-methyl-1β-((E)-2-phenylethenyl)cyclopropane-1α-carboxylate
• 英文别名: methyl (1R,2R,3R)-2-ethoxy-3-methyl-1-[(E)-2-phenylethenyl]cyclopropane-1-carboxylate
• CAS: 140928-57-0
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: ZJWQBJZSSBEASZ-AXPYJTKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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-((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77%的产率得到Methyl (3β,4α,5α)-4-ethoxy-5-methyl-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：

  乙基丙烯醚 、 (E)-methyl 2-diazo-4-phenylbut-3-enoate 在 rhodium(II) pivalate 作用下， 以 正戊烷 为溶剂， 以80%的产率得到Methyl 2β-ethoxy-3β-methyl-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

• Asymmetric Synthesis of Cyclopentenes by [3 + 2] Annulations between Vinylcarbenoids and Vinyl Ethers
  作者：Huw M. L. Davies、Norman Kong、Melvyn Rowen Churchill

  DOI：10.1021/jo980738n

  日期：1998.9.1

  Rhodium N-(dodecylbenzenesulfonyl)prolinate [(Rh-2(S-DOSP)(4) (1)]-catalyzed decomposition of diazobutenoates in the presence of vinyl ethers results in highly diastereoselective and enantioselective synthesis of donor/acceptor-substituted vinylcyclopropanes. Diethylaluminum chloride-induced rearrangement of these vinylcyclopropanes results in the formation of cyclopentenes with excellent control of diastereoselectivity and for the fused cyclopentenes good control of absolute stereochemistry. This study illustrates the synthetic utility of Rh-2(S-DOSP)(4) as a chiral catalyst for vinylcarbenoid cyclopropanations and the remarkable diastereocontrol that is possible in the diethylaluminum chloride-induced ring expansion of donor/acceptor-substituted vinylcyclopropanes.
• 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.