4,9-dimethyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 1443647-01-5

• 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: 4,9-dimethyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 4,9-dimethyl-2-(4-methylphenyl)sulfonyl-3,4-dihydro-1H-pyrido[3,4-b]indole
• CAS: 1443647-01-5
• 化学式: C₂₀H₂₂N₂O₂S
• 分子量: 354.473
• InChiKey: SONMBZBFNCZPMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,9-dimethyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 在 萘 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到4,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Cascade Electrophilic Iodocyclization: Efficient Preparation of 4-Iodomethyl Substituted Tetrahydro-β-carbolines and Formal Synthesis of Oxopropaline G

  摘要：

  4-Iodomethyl substituted tetrahydro-beta-carbolines, the core structure of numerous natural products and bioactive molecules, are readily prepared via I-2-promoted cascade electrophilic cyclization. The reactivity differences of olefins and alkynes ensure that the reaction proceeds smoothly. This methodology was successfully applied to the formal synthesis of oxopropaline G.

  DOI：

  10.1021/ol401303f
• 作为产物：
  描述：

  4-甲基-N-(丙-2-炔-1-基)苯-1-磺酰胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 34.0h， 生成 4,9-dimethyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Cascade Electrophilic Iodocyclization: Efficient Preparation of 4-Iodomethyl Substituted Tetrahydro-β-carbolines and Formal Synthesis of Oxopropaline G

  摘要：

  4-Iodomethyl substituted tetrahydro-beta-carbolines, the core structure of numerous natural products and bioactive molecules, are readily prepared via I-2-promoted cascade electrophilic cyclization. The reactivity differences of olefins and alkynes ensure that the reaction proceeds smoothly. This methodology was successfully applied to the formal synthesis of oxopropaline G.

  DOI：

  10.1021/ol401303f

文献信息

• Cascade Electrophilic Iodocyclization: Efficient Preparation of 4-Iodomethyl Substituted Tetrahydro-β-carbolines and Formal Synthesis of Oxopropaline G
  作者：Hongjian Song、Yongxian Liu、Qingmin Wang

  DOI：10.1021/ol401303f

  日期：2013.7.5

  4-Iodomethyl substituted tetrahydro-beta-carbolines, the core structure of numerous natural products and bioactive molecules, are readily prepared via I-2-promoted cascade electrophilic cyclization. The reactivity differences of olefins and alkynes ensure that the reaction proceeds smoothly. This methodology was successfully applied to the formal synthesis of oxopropaline G.