N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]phenylmethyl]-4-methylbenzenesulfonamide | 452897-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]phenylmethyl]-4-methylbenzenesulfonamide
• 英文别名: N-{[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-phenyl-methyl}-4-methyl-benzenesulfonamide；N-[[1-[tert-butyl(dimethyl)silyl]indol-3-yl]-phenylmethyl]-4-methylbenzenesulfonamide
• CAS: 452897-57-3
• 化学式: C₂₈H₃₄N₂O₂SSi
• 分子量: 490.742
• InChiKey: VFSPFOIOSCOZDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]phenylmethyl]-4-methylbenzenesulfonamide 在 Bentonite K-10 clay 、 sodium ethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 5-(tert-Butyl-dimethyl-silanyl)-1-phenyl-1,2,3,5-tetrahydro-pyrido[4,3-b]indol-4-one
  参考文献：
  名称：

  Syntheses of Functionalized 1,4-Disubstituted γ-Carbolines

  摘要：

  We report the complete synthesis of a variety of 1,4-disubstituted gamma-carbolines. These compounds are of particular interest for their involvement in many biological processes and are believed to possess various medicinal activities. A large number of N-tosylaldimines were condensed with indoles affording an array of 3-aminomethyl indoles. Subsequent additions, followed by intramolecular cyclization, afforded an array of 1,2-dihydro-3H-gamma-carbolones in good yield. Upon subsequent aromatization, the corresponding fully aromatic functionalized 1-aryl-4-hydroxy-gamma-carbolines resulted.

  DOI：

  10.1021/jo034290o
• 作为产物：
  描述：

  N-tert-butyldimethylsilylindole 在 N-溴代丁二酰亚胺(NBS) 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 16.25h， 生成 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]phenylmethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  3-[（1-芳基）氨基甲基]吲哚的合成。

  摘要：

  我们报告了各种高度功能化的3-芳基氨基甲基吲哚的新型合成。这种合成方法利用了庞大的叔丁基二甲基甲硅烷基保护基的定向能力，该保护基可将一系列芳香族甲苯磺醛亚胺的缩合特异性地引入吲哚核的3位。在相对温和的条件下发生的反应以中等收率提供了所需的产物。在选择性切割保护基之前，官能化的被保护的吲哚还充当许多未来有机转化的有吸引力的底物。

  DOI：

  10.1021/jo020049i

文献信息

• Synthesized γ-carbolines
  申请人：Wynne James H.

  公开号：US06872830B1

  公开（公告）日：2005-03-29

  The present invention concerns the compounds of the formula: and the prodrug and salts thereof, wherein R may be a hydroxyl or other pendent group and Ar is an aryl. The compositions may be adapted for the treatment of neurodegenerative diseases. Further, the compositions may be adapted as a pharmaceutical such as an antipsychotic pharmaceutical, an antibiotic pharmaceutical, an antiviral pharmaceutical or an antitumor pharmaceutical.

  本发明涉及以下式的化合物及其前药和盐：其中R可能是羟基或其他侧链基团，Ar是芳基。这些组合物可以用于神经退行性疾病的治疗。此外，这些组合物可以用作药物，如抗精神病药物、抗生素药物、抗病毒药物或抗肿瘤药物。
• Syntheses of Functionalized 1,4-Disubstituted γ-Carbolines
  作者：James H. Wynne、Wayne M. Stalick

  DOI：10.1021/jo034290o

  日期：2003.6.1

  We report the complete synthesis of a variety of 1,4-disubstituted gamma-carbolines. These compounds are of particular interest for their involvement in many biological processes and are believed to possess various medicinal activities. A large number of N-tosylaldimines were condensed with indoles affording an array of 3-aminomethyl indoles. Subsequent additions, followed by intramolecular cyclization, afforded an array of 1,2-dihydro-3H-gamma-carbolones in good yield. Upon subsequent aromatization, the corresponding fully aromatic functionalized 1-aryl-4-hydroxy-gamma-carbolines resulted.
• Synthesis of 3-[(1-Aryl)aminomethyl]indoles
  作者：James H. Wynne、Wayne M. Stalick

  DOI：10.1021/jo020049i

  日期：2002.8.1

  We report the novel synthesis of various highly functionalized 3-arylaminomethyl indoles. This synthetic approach makes use of the directing ability of a bulky tert-butyldimethylsilyl-protecting group, which directs the condensation of an array of aromatic tosylaldimines specifically into the 3-position of the indole nucleus. The reactions, which occur under relatively mild conditions, afford the desired

  我们报告了各种高度功能化的3-芳基氨基甲基吲哚的新型合成。这种合成方法利用了庞大的叔丁基二甲基甲硅烷基保护基的定向能力，该保护基可将一系列芳香族甲苯磺醛亚胺的缩合特异性地引入吲哚核的3位。在相对温和的条件下发生的反应以中等收率提供了所需的产物。在选择性切割保护基之前，官能化的被保护的吲哚还充当许多未来有机转化的有吸引力的底物。