ethyl 3-(phenylsulfonyl)cyclohepta-1,3,5-trien-1-oate | 134455-10-0

• 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: ethyl 3-(phenylsulfonyl)cyclohepta-1,3,5-trien-1-oate
• 英文别名: Ethyl 3-(benzenesulfonyl)cyclohepta-1,3,5-triene-1-carboxylate
• CAS: 134455-10-0
• 化学式: C₁₆H₁₆O₄S
• 分子量: 304.367
• InChiKey: LEQLZHKGUXMKSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (E)-2-diazo-4-(phenylsulfonyl)-3-butenoate 在 rhodium(II) acetate dimer 、 三乙胺 作用下， 生成 ethyl 3-(phenylsulfonyl)cyclohepta-1,3,5-trien-1-oate
  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：——