dimethyl (3S*,4aR*,9aS*)-9-methyl-3-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydro-9H-4a,9a-propanocarbazole-1,1-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: dimethyl (3S*,4aR*,9aS*)-9-methyl-3-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydro-9H-4a,9a-propanocarbazole-1,1-dicarboxylate
• 英文别名: dimethyl (1R,9S,14S)-8-methyl-14-[(E)-2-phenylethenyl]-8-azatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6-triene-16,16-dicarboxylate
• 化学式: C₂₈H₃₁NO₄
• 分子量: 445.558
• InChiKey: GAHHYNWRPSTTNR-WFERBOMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4,9-四氢-9-甲基-1H-咔唑 、 dimethyl (E)-2-styrylcyclopropane-1,1-dicarboxylate 在 ytterbium(III) triflate 作用下， 以 乙腈 为溶剂， 反应 168.0h， 生成 dimethyl (3S*,4aR*,9aS*)-9-methyl-3-[(E)-2-phenylethenyl]-1,2,3,4-tetrahydro-9H-4a,9a-propanocarbazole-1,1-dicarboxylate 、 dimethyl (1R,9S,14R)-8-methyl-14-[(E)-2-phenylethenyl]-8-azatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6-triene-16,16-dicarboxylate
  参考文献：
  名称：

  Cyclopentannulation of 3-Alkylindoles:  A Synthesis of a Tetracyclic Subunit of the Kopsane Alkaloids

  摘要：

  Indoles which bear an alkyl substituent in the 3-position undergo a [3 + 2] annulation reaction when treated with 1,1-cyclopropane diesters in the presence of Yb(OTf)(3) resulting in 2,3-cyclopentanoindolines. Typically, the reactions are performed at elevated temperatures or at ultrahigh pressures. In cases where steric crowding is an issue, ultrahigh pressures are required. In reactions involving substituted cyclopropanes, significant regio- and diastereocontrol was observed. When the substituent was aromatic or olefinic, the reactions took place at ambient temperature and pressure. The applicability of this methodology to the preparation of a key tetracyclic subunit of the kopsane alkaloids was demonstrated.

  DOI：

  10.1021/jo015643r

文献信息

• Cyclopentannulation of 3-Alkylindoles:  A Synthesis of a Tetracyclic Subunit of the Kopsane Alkaloids
  作者：Dylan B. England、Timothy D. O. Kuss、Ryan G. Keddy、Michael A. Kerr

  DOI：10.1021/jo015643r

  日期：2001.6.1

  Indoles which bear an alkyl substituent in the 3-position undergo a [3 + 2] annulation reaction when treated with 1,1-cyclopropane diesters in the presence of Yb(OTf)(3) resulting in 2,3-cyclopentanoindolines. Typically, the reactions are performed at elevated temperatures or at ultrahigh pressures. In cases where steric crowding is an issue, ultrahigh pressures are required. In reactions involving substituted cyclopropanes, significant regio- and diastereocontrol was observed. When the substituent was aromatic or olefinic, the reactions took place at ambient temperature and pressure. The applicability of this methodology to the preparation of a key tetracyclic subunit of the kopsane alkaloids was demonstrated.