cyclohex-2-enyl 1-phenylcycloprop-2-enecarboxylate | 1427729-66-5

• 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: cyclohex-2-enyl 1-phenylcycloprop-2-enecarboxylate
• 英文别名: Cyclohex-2-en-1-yl 1-phenylcycloprop-2-ene-1-carboxylate；cyclohex-2-en-1-yl 1-phenylcycloprop-2-ene-1-carboxylate
• CAS: 1427729-66-5
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: HBQALBQHKVRVTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclohex-2-enyl 1-phenylcycloprop-2-enecarboxylate 在 rhodium(II) pivalate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以90.476%的产率得到
  参考文献：
  名称：

  Selective Syntheses of Δ^α,β and Δ^β,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements

  摘要：

  Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Delta(beta,gamma) butenolides via a Cialsen rearrangement or to the corresponding Delta(alpha,beta) butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.

  DOI：

  10.1021/ol400264a
• 作为产物：
  描述：

  2-环己烯醇 、 1-苯基环丙基-2-烯-1-羧酸 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以59%的产率得到cyclohex-2-enyl 1-phenylcycloprop-2-enecarboxylate
  参考文献：
  名称：

  Selective Syntheses of Δ^α,β and Δ^β,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements

  摘要：

  Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Delta(beta,gamma) butenolides via a Cialsen rearrangement or to the corresponding Delta(alpha,beta) butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.

  DOI：

  10.1021/ol400264a

文献信息

• Selective Syntheses of Δ^α,β and Δ^β,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements
  作者：Xiaocong Xie、Yi Li、Joseph M. Fox

  DOI：10.1021/ol400264a

  日期：2013.4.5

  Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Delta(beta,gamma) butenolides via a Cialsen rearrangement or to the corresponding Delta(alpha,beta) butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.