(1R*,3S*,3aS*,8bR*)-1,3,3a,8b-tetrahydro-1-hydroxy-4-(methylsulfonyl)-3-[1-(methylsulfonyl)indol-3-yl]furo[3,4-b]indole

• 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: (1R*,3S*,3aS*,8bR*)-1,3,3a,8b-tetrahydro-1-hydroxy-4-(methylsulfonyl)-3-[1-(methylsulfonyl)indol-3-yl]furo[3,4-b]indole
• 英文别名: (1R,3S,3aS,8bR)-4-methylsulfonyl-3-(1-methylsulfonylindol-3-yl)-1,3,3a,8b-tetrahydrofuro[3,4-b]indol-1-ol
• 化学式: C₂₀H₂₀N₂O₆S₂
• 分子量: 448.521
• InChiKey: OJOFRTGPPPJIQS-FUMNGEBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R*,3S*,3aS*,8bR*)-1,3,3a,8b-tetrahydro-1-hydroxy-4-(methylsulfonyl)-3-[1-(methylsulfonyl)indol-3-yl]furo[3,4-b]indole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 16.0h， 以57%的产率得到(3S*,3aS*,8bR*)-3a,8b-dihydro-4-(methylsulfonyl)-3-[1-(methylsulfonyl)indol-3-yl]furo[3,4-b]indol-1-one
  参考文献：
  名称：

  Indolecarbonyl Coupling Reactions Promoted by Samarium Diiodide. Application to the Synthesis of Indole-Fused Compounds

  摘要：

  By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl)indole-3-carboxaldehydes were realized as the indole-carbonyl group was more reactive toward SmI2 than the aliphatic carbonyl group. Elaboration of the coupling products with oxidizing agents, acid, phosphorus pentasulfide (or Lawesson's reagent), amines, and hydrazine led to a variety of indole derivatives and indole-fused polycyclic compounds of synthetic interest and pharmaceutical uses.

  DOI：

  10.1021/jo9720795
• 作为产物：
  描述：

  1-(甲磺酰基)-1H-吲哚-3-甲醛 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1,3,3a,8b-tetrahydro-1-hydroxy-4-(methylsulfonyl)-3-[1-(methylsulfonyl)indol-3-yl]furo[3,4-b]indole 、 (1R*,3S*,3aS*,8bR*)-1,3,3a,8b-tetrahydro-1-hydroxy-4-(methylsulfonyl)-3-[1-(methylsulfonyl)indol-3-yl]furo[3,4-b]indole
  参考文献：
  名称：

  Indolecarbonyl Coupling Reactions Promoted by Samarium Diiodide. Application to the Synthesis of Indole-Fused Compounds

  摘要：

  By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl)indole-3-carboxaldehydes were realized as the indole-carbonyl group was more reactive toward SmI2 than the aliphatic carbonyl group. Elaboration of the coupling products with oxidizing agents, acid, phosphorus pentasulfide (or Lawesson's reagent), amines, and hydrazine led to a variety of indole derivatives and indole-fused polycyclic compounds of synthetic interest and pharmaceutical uses.

  DOI：

  10.1021/jo9720795

文献信息

• Indolecarbonyl Coupling Reactions Promoted by Samarium Diiodide. Application to the Synthesis of Indole-Fused Compounds
  作者：Shu-Chen Lin、Fwu-Duo Yang、Jiann-Shyng Shiue、Shyh-Ming Yang、Jim-Min Fang

  DOI：10.1021/jo9720795

  日期：1998.5.1

  By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl)indole-3-carboxaldehydes were realized as the indole-carbonyl group was more reactive toward SmI2 than the aliphatic carbonyl group. Elaboration of the coupling products with oxidizing agents, acid, phosphorus pentasulfide (or Lawesson's reagent), amines, and hydrazine led to a variety of indole derivatives and indole-fused polycyclic compounds of synthetic interest and pharmaceutical uses.