ethyl 4-(ethoxycarbonyl)-7-methyl-6-methylene-octa-3(E),7-dienoate | 134418-98-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-(ethoxycarbonyl)-7-methyl-6-methylene-octa-3(E),7-dienoate
• 英文别名: diethyl (E)-2-(3-methyl-2-methylidenebut-3-enyl)pent-2-enedioate
• CAS: 134418-98-7
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: CWJHSOPKHOATHC-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl (E)-4-diazopent-2-enedioate 、 2,3-二甲基-1,3-丁二烯 、 乙酸铑(II)二聚物二水合物 以13%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• 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.