6,6-dimethoxycarbonyl-7a-methyl-1,4,5,6,7,7a-hexahydroinden-2-one

• 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: 6,6-dimethoxycarbonyl-7a-methyl-1,4,5,6,7,7a-hexahydroinden-2-one
• 英文别名: 4,4-bismethoxycarbonyl-6-methylbicyclo[4.3.0]non-1(9)-en-8-one；Dimethyl 3a-methyl-2-oxo-3,4,6,7-tetrahydroindene-5,5-dicarboxylate
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: AIALAABPDUAVKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl 2-(but-3-ynyl)malonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 6,6-dimethoxycarbonyl-7a-methyl-1,4,5,6,7,7a-hexahydroinden-2-one
  参考文献：
  名称：

  Investigation of Intramolecular Pauson-Khand Reaction of 2-Aryl-1,6- and 1-Methyl-1,7-enynes (exo-Olefins) and 1-Phenyl-1-octen-7-yne (endo-Olefin)

  摘要：

  The intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivatives (exo-olefins) efficiently produced arylbicyclo[3.3.0]octenones and azaoctenone bearing quaternary carbon centers at angular positions in good yields. Although a similar reaction of 2-phenyl-1-octen-7-yne (exo-olefin), which is a homologue of 2-phenyl-1-hepten-6-yne, did not take place, the reaction of the methyl derivatives smoothly proceeded. However, the reaction of regioisomeric 1-phenyl-1-octen-7-yne (endo-olefin) afforded the desired product in moderate yields.

  DOI：

  10.3987/com-03-9993

文献信息

• Intramolecular Pauson-Khand Reaction of Various 2-Aryl-1,6-Enynes: Synthesis of Bicyclic Compounds Bearing Quaternary Carbon Center
  作者：Miyuki Ishizaki、Hiroshi Satoh、Osamu Hoshino

  DOI：10.1246/cl.2002.1040

  日期：2002.10

  Intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivative (acyclic exo-methylene compounds) efficiently produced 1-aryl-bicyclo[3.3.0] octenones and azaoctenone bearing quaternary carbon center in good yields. The reaction of 1,7-enynes was also investigated.

  各种 2-芳基-1-庚烯-6-炔及其氮杂衍生物（无环外亚甲基化合物）的分子内 Pauson-Khand 反应有效地产生了 1-芳基-双环 [3.3.0] 辛烯酮和带有季碳中心的氮杂辛烯酮良好的收益。还研究了 1,7-烯炔的反应。
• Rh(I)-catalyzed intramolecular [2 + 2 + 1] cycloaddition of allenenes: Construction of bicyclo[4.3.0]nonenones with an angular methyl group and tricyclo[6.4.0.0^1,5]dodecenone
  作者：Fuyuhiko Inagaki、Naoya Itoh、Yujiro Hayashi、Yumi Matsui、Chisato Mukai

  DOI：10.3762/bjoc.7.52

  日期：——

  The [RhCl(CO)dppp](2)-catalyzed intramolecular carbonylative [2 + 2 + 1] cycloaddition of allenenes was developed to prepare bicyclo[4.3.0]nonenones possessing a methyl group at the ring junction, which is difficult to achieve by the Pauson-Khand reaction of the corresponding enynes. This method also provided a new procedure for the construction of the tricyclo[6.4.0.0(1,5)]dodecenone framework in

  开发了[RhCl(CO)dppp](2)-催化的丙二烯分子内羰基化[2+2+1]环加成反应来制备双环[4.3.0]壬烯酮在环连接处具有甲基，这很难实现通过相应烯炔的 Pauson-Khand 反应。该方法还为以令人满意的产率构建三环[6.4.0.0(1,5)]十二烯酮骨架提供了一种新方法。
• Investigation of Intramolecular Pauson-Khand Reaction of 2-Aryl-1,6- and 1-Methyl-1,7-enynes (exo-Olefins) and 1-Phenyl-1-octen-7-yne (endo-Olefin)
  作者：Miyuki Ishizaki、Hiroshi Satoh、Osamu Hoshino、Kiyoshi Nishitani、Hiroshi Hara

  DOI：10.3987/com-03-9993

  日期：——

  The intramolecular Pauson-Khand reaction of various 2-aryl-1-hepten-6-ynes and its aza-derivatives (exo-olefins) efficiently produced arylbicyclo[3.3.0]octenones and azaoctenone bearing quaternary carbon centers at angular positions in good yields. Although a similar reaction of 2-phenyl-1-octen-7-yne (exo-olefin), which is a homologue of 2-phenyl-1-hepten-6-yne, did not take place, the reaction of the methyl derivatives smoothly proceeded. However, the reaction of regioisomeric 1-phenyl-1-octen-7-yne (endo-olefin) afforded the desired product in moderate yields.