(2aR,4aR,6aS,9aS,9bR,9cR)-3-Methylene-dodecahydro-cyclohepta[jkl]-as-indacene-1,1,6,6-tetracarboxylic acid tetramethyl ester | 136569-42-1

• 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: (2aR,4aR,6aS,9aS,9bR,9cR)-3-Methylene-dodecahydro-cyclohepta[jkl]-as-indacene-1,1,6,6-tetracarboxylic acid tetramethyl ester
• 英文别名: tetramethyl (1R,4S,8S,11R,14R,15R)-12-methylidenetetracyclo[6.5.2.04,14.011,15]pentadecane-3,3,9,9-tetracarboxylate
• CAS: 136569-42-1
• 化学式: C₂₄H₃₂O₈
• 分子量: 448.513
• InChiKey: OYMSMOHXJGUIPB-NXBFSHDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  dimethyl 2-[(E)-4-acetyloxybut-2-enyl]-2-[(1R,4R)-4-(1-methoxy-2-methoxycarbonyl-1-oxopent-4-en-2-yl)cyclohept-2-en-1-yl]propanedioate 在 三(2-呋喃基)膦 、 Pd(dibenzylideneacetone) 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以50%的产率得到(2aR,4aR,6aS,9aS,9bR,9cR)-3-Methylene-dodecahydro-cyclohepta[jkl]-as-indacene-1,1,6,6-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Direct syntheses of polyfused ring systems by intramolecular tandem palladium-ene/Heck insertion reactions

  摘要：

  The Pd(0)-catalyzed polycyclizations 1 --> 3 + 4, 5 --> 9 and 6 --> 10 are described. The stereospecifity of these transformations is ascribed to an intramolecular suprafacial "palladium-ene" process followed by one to two "Heck-insertions" proceeding with retention of configuration at the metalated carbon.

  DOI：

  10.1021/jo00022a004

文献信息

• Direct syntheses of polyfused ring systems by intramolecular tandem palladium-ene/Heck insertion reactions
  作者：Wolfgang Oppolzer、Robert J. DeVita

  DOI：10.1021/jo00022a004

  日期：1991.10

  The Pd(0)-catalyzed polycyclizations 1 --> 3 + 4, 5 --> 9 and 6 --> 10 are described. The stereospecifity of these transformations is ascribed to an intramolecular suprafacial "palladium-ene" process followed by one to two "Heck-insertions" proceeding with retention of configuration at the metalated carbon.