2-Methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole | 573710-99-3

• 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: 2-Methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole
• CAS: 573710-99-3
• 化学式: C₁₂H₁₃NS
• 分子量: 203.308
• InChiKey: LGNFPFBAIXBGNO-UHFFFAOYSA-N

物化性质

• 沸点：
  372.6±21.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-diazo-4-methyl-pent-3-enoic acid ethyl ester 、 2-Methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到ethyl (E)-4-[(2R,4aS)-2-methyl-3,4-dihydro-2H-thiopyrano[2,3-b]indol-4a-yl]-4-methylpent-2-enoate
  参考文献：
  名称：

  Diastereoselective synthesis of quaternary substituted thioindolines from sulfur ylide intermediates

  摘要：

  We have examined the coupling reactions of 2-thioindoles with vinyl diazoacetates in the presence of Rh(11) catalysts. While attempted enantio- and/or diastereoselective couplings using chiral catalysts and/or chiral auxiliaries on the vinyl diazoacetate have been largely unsuccessful, substrates having resident chirality on fused thiopyrans gave thioindolines with moderate to high diastereoselectivities. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00077-6
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 3-(1H-indol-3-yl)-1-methyl-propyl ester 在 氢氧化钾 、 碘 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Methyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole
  参考文献：
  名称：

  Diastereoselective synthesis of quaternary substituted thioindolines from sulfur ylide intermediates

  摘要：

  We have examined the coupling reactions of 2-thioindoles with vinyl diazoacetates in the presence of Rh(11) catalysts. While attempted enantio- and/or diastereoselective couplings using chiral catalysts and/or chiral auxiliaries on the vinyl diazoacetate have been largely unsuccessful, substrates having resident chirality on fused thiopyrans gave thioindolines with moderate to high diastereoselectivities. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00077-6