methyl (3aS,4S,7S,7aR,9R)-2,2,7-trimethyl-8-oxo-3a,4,7,7a-tetrahydro-4,7-ethanobenzo[d][1,3]dioxole-9-carboxylate | 1236459-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3aS,4S,7S,7aR,9R)-2,2,7-trimethyl-8-oxo-3a,4,7,7a-tetrahydro-4,7-ethanobenzo[d][1,3]dioxole-9-carboxylate
• CAS: 1236459-37-2
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: QMWRDZBTKXPGCB-YHZHVHRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (3aS,4S,7S,7aR,9R)-2,2,7-trimethyl-8-oxo-3a,4,7,7a-tetrahydro-4,7-ethanobenzo[d][1,3]dioxole-9-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以58%的产率得到methyl (3aR,4R,7S,7aS,8R,9R)-9-hydroxy-2,2,4-trimethyl-3a,4,7,7a-tetrahydro-4,7-ethanobenzo[d][1,3]dioxole-8-carboxylate
  参考文献：
  名称：

  Chemoenzymatic and enantioselective assembly of the (1α,3aβ,6α,7aβ)-octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: validation of a new synthetic strategy and the identification of enantiomeric switching regimes

  摘要：

  The octahydro-1,6-methano-1H-indene framework associated with the marine sesquiterpenoid 2-isocyanoallopupukeanane (1) has been prepared in enantiomerically pure form from the cis-1,2-dihydrocatechol 8 using Diels-Alder cycloaddition, oxa-di-pi-methane rearrangement and intramolecular enolate alkylation steps as the key bond-forming events. Three distinct strategies for employing such sequences in the selective synthesis of either enantiomeric form of the target framework have been identified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.056
• 作为产物：
  描述：

  氰基甲酸甲酯 、 (3aS,4R,7S,7aR)-3a,4,7,7a-tetrahydro-2,2,7-trimethyl-4,7-ethano-1,3-benzodioxol-8-one 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 以67%的产率得到methyl (3aS,4S,7S,7aR,9R)-2,2,7-trimethyl-8-oxo-3a,4,7,7a-tetrahydro-4,7-ethanobenzo[d][1,3]dioxole-9-carboxylate
  参考文献：
  名称：

  Chemoenzymatic and enantioselective assembly of the (1α,3aβ,6α,7aβ)-octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: validation of a new synthetic strategy and the identification of enantiomeric switching regimes

  摘要：

  The octahydro-1,6-methano-1H-indene framework associated with the marine sesquiterpenoid 2-isocyanoallopupukeanane (1) has been prepared in enantiomerically pure form from the cis-1,2-dihydrocatechol 8 using Diels-Alder cycloaddition, oxa-di-pi-methane rearrangement and intramolecular enolate alkylation steps as the key bond-forming events. Three distinct strategies for employing such sequences in the selective synthesis of either enantiomeric form of the target framework have been identified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.056