diethyl 2-<(3-carbonitrile)-3-cyclopentenyl> propanedioate | 146467-02-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2-<(3-carbonitrile)-3-cyclopentenyl> propanedioate
• 英文别名: Diethyl 2-(3-cyanocyclopent-3-en-1-yl)propanedioate
• CAS: 146467-02-9
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: KSZJDYVXMDSWDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-<(3-carbonitrile)-3-cyclopentenyl> propanedioate 在 六甲基磷酰三胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 potassium hydride 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 Bicyclo[3.2.1]octane-2,2-dicarboxylic acid, 6-cyano-4-methylene-,diethyl ester, endo-
  参考文献：
  名称：

  Approaches to bicyclic ring systems via 1,5 allylic abstraction cyclisation

  摘要：

  A new 1, 5 allylic abstraction, cyclisation sequence has been developed and applied to the synthesis of fused bicyclic systems. Initial studies directed towards the synthesis of the bicyclo[3.3.0] octane skeleton are described. vinyl bromide 4 was subjected to standard cyclisation conditions to give 5 as a single isomer. Further studies were directly related to the development of the rearrangement sequence: vinyl bromide 10 was subject to cyclisation conditions to give 12 in moderate yield. A significant improvement in the rate and efficiency of this type of conversion was achieved by introducing an electron withdrawing group on the acceptor alkene, thus compound 17 gives 18 in excellent yield.

  DOI：

  10.1016/s0040-4020(01)88361-7
• 作为产物：
  描述：

  diethyl 2-(3-oxocyclopentyl)malonate 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 diethyl 2-<(3-carbonitrile)-3-cyclopentenyl> propanedioate
  参考文献：
  名称：

  Approaches to bicyclic ring systems via 1,5 allylic abstraction cyclisation

  摘要：

  A new 1, 5 allylic abstraction, cyclisation sequence has been developed and applied to the synthesis of fused bicyclic systems. Initial studies directed towards the synthesis of the bicyclo[3.3.0] octane skeleton are described. vinyl bromide 4 was subjected to standard cyclisation conditions to give 5 as a single isomer. Further studies were directly related to the development of the rearrangement sequence: vinyl bromide 10 was subject to cyclisation conditions to give 12 in moderate yield. A significant improvement in the rate and efficiency of this type of conversion was achieved by introducing an electron withdrawing group on the acceptor alkene, thus compound 17 gives 18 in excellent yield.

  DOI：

  10.1016/s0040-4020(01)88361-7

文献信息

• Approaches to bicyclic ring systems via 1,5 allylic abstraction cyclisation
  作者：A.D. Borthwick、S. Caddick、P.J. Parsons

  DOI：10.1016/s0040-4020(01)88361-7

  日期：1992.11

  A new 1, 5 allylic abstraction, cyclisation sequence has been developed and applied to the synthesis of fused bicyclic systems. Initial studies directed towards the synthesis of the bicyclo[3.3.0] octane skeleton are described. vinyl bromide 4 was subjected to standard cyclisation conditions to give 5 as a single isomer. Further studies were directly related to the development of the rearrangement sequence: vinyl bromide 10 was subject to cyclisation conditions to give 12 in moderate yield. A significant improvement in the rate and efficiency of this type of conversion was achieved by introducing an electron withdrawing group on the acceptor alkene, thus compound 17 gives 18 in excellent yield.