[[[1-(tert-butyldimethylsilyl)-1H-indol-3-yl](pyridin-2-yl)methyl]-(toluene-4-sulfonyl)amino]acetic acid ethyl ester | 568588-94-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [[[1-(tert-butyldimethylsilyl)-1H-indol-3-yl](pyridin-2-yl)methyl]-(toluene-4-sulfonyl)amino]acetic acid ethyl ester
• 英文别名: [[[1-TBDMS-1H-indol-3-yl]-pyridin-2-yl-methyl]-(toluene-4-sulfonyl)-amino]-acetic acid ethyl ester；Ethyl 2-[[[1-[tert-butyl(dimethyl)silyl]indol-3-yl]-pyridin-2-ylmethyl]-(4-methylphenyl)sulfonylamino]acetate
• CAS: 568588-94-3
• 化学式: C₃₁H₃₉N₃O₄SSi
• 分子量: 577.82
• InChiKey: XPLPHLHALHCCIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [[[1-(tert-butyldimethylsilyl)-1H-indol-3-yl](pyridin-2-yl)methyl]-(toluene-4-sulfonyl)amino]acetic acid ethyl ester 在 Bentonite K-10 clay 、 sodium hydroxide 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以33%的产率得到1-(pyridin-2-yl)-5H-pyrido[4,3-b]indol-4-ol
  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：

  3-bromo-1-(tert-butyldimethylsilyl)indole 在 叔丁基锂 、 sodium ethanolate 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 27.75h， 生成 [[[1-(tert-butyldimethylsilyl)-1H-indol-3-yl](pyridin-2-yl)methyl]-(toluene-4-sulfonyl)amino]acetic acid ethyl ester
  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

文献信息

• 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.