ethyl 5,6-dimethyl-3-((E)-2-phenylethenyl)cyclohepta-1,5-diene-1-carboxylate | 134418-97-6

• 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: ethyl 5,6-dimethyl-3-((E)-2-phenylethenyl)cyclohepta-1,5-diene-1-carboxylate
• 英文别名: ethyl 5,6-dimethyl-3-[(E)-2-phenylethenyl]cyclohepta-1,5-diene-1-carboxylate
• CAS: 134418-97-6
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: KKBSNDCUGJRIKP-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-己二烯酸,6-苯基-,乙基酯,(E,E)- 在 rhodium(II) hexanoate 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.67h， 生成 ethyl 5,6-dimethyl-3-((E)-2-phenylethenyl)cyclohepta-1,5-diene-1-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of seven-membered carbocycles by a tandem cyclopropanation/Cope rearrangement between rhodium(II)-stabilized vinylcarbenoids and dienes

  摘要：

  Rhodium (II)-catalyzed decomposition of vinyldiazomethanes in the presence of dienes generated 1,4-cycloheptadienes by a tandem cyclopropanation/Cope rearrangement. Excellent stereocontrol of up to three stereogenic centers in the cycloheptadienes was achieved. The stereoselectivity of the initial cyclopropanation ranged from 4:1 to > 20:1, favoring cis-divinylcyclopropanes, and good regiocontrol was observed in the cyclopropanation of unsymmetrical dienes. Unless sterically encumbered, the cis-divinylcyclopropanes rearranged cleanly to cycloheptadienes under the reaction conditions. The trans-divinylcyclopropanes, when formed, were sufficiently stable to be observed in the crude reaction mixtures, but most were prone to facile 1,5-homodienyl rearrangements.

  DOI：

  10.1021/jo00012a011

文献信息

• DAVIES, HUW M. L.;CLARK, T. JEFFREY;SMITH, H. DAVID, J. ORG. CHEM., 56,(1991) N2, C. 3817-3824
  作者：DAVIES, HUW M. L.、CLARK, T. JEFFREY、SMITH, H. DAVID

  DOI：——

  日期：——
• Stereoselective synthesis of seven-membered carbocycles by a tandem cyclopropanation/Cope rearrangement between rhodium(II)-stabilized vinylcarbenoids and dienes
  作者：Huw M. L. Davies、T. Jeffrey Clark、H. David Smith

  DOI：10.1021/jo00012a011

  日期：1991.6

  Rhodium (II)-catalyzed decomposition of vinyldiazomethanes in the presence of dienes generated 1,4-cycloheptadienes by a tandem cyclopropanation/Cope rearrangement. Excellent stereocontrol of up to three stereogenic centers in the cycloheptadienes was achieved. The stereoselectivity of the initial cyclopropanation ranged from 4:1 to > 20:1, favoring cis-divinylcyclopropanes, and good regiocontrol was observed in the cyclopropanation of unsymmetrical dienes. Unless sterically encumbered, the cis-divinylcyclopropanes rearranged cleanly to cycloheptadienes under the reaction conditions. The trans-divinylcyclopropanes, when formed, were sufficiently stable to be observed in the crude reaction mixtures, but most were prone to facile 1,5-homodienyl rearrangements.