tert-butyl 9-((3-(4-cyano-2,6-dimethylheptan-4-yl)-4-methoxyphenyl)sulfonyl)-1-propyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate | 1620581-61-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: tert-butyl 9-((3-(4-cyano-2,6-dimethylheptan-4-yl)-4-methoxyphenyl)sulfonyl)-1-propyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate
• CAS: 1620581-61-4
• 化学式: C₃₆H₄₉N₃O₅S
• 分子量: 635.868
• InChiKey: FNUNYSBITLUCKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.37
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  101.63
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 9-((3-(4-cyano-2,6-dimethylheptan-4-yl)-4-methoxyphenyl)sulfonyl)-1-propyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate 、 丙烯酸乙酯 在 silver(I) acetate 、 palladium diacetate 、 N-乙酰甘氨酸 作用下， 反应 24.0h， 以58%的产率得到(E)-tert-butyl 9-((3-(4-cyano-2,6-dimethylheptan-4-yl)-4-methoxyphenyl)sulfonyl)-7-(3-ethoxy-3-oxoprop-1-en-1-yl)-1-propyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate
  参考文献：
  名称：

  Pd(II)-Catalyzed meta-C–H Olefination, Arylation, and Acetoxylation of Indolines Using a U-Shaped Template

  摘要：

  meta-C-H olefination, arylation, and acetoxylation of indolines have been developed using nitrile-containing templates. The combination of a monoprotected amino acid ligand and the nitrile template attached at the indolinyl nitrogen via a sulfonamide linkage is crucial for the meta-selective C-H fiunctionalization of electron-rich indolines that are otherwise highly reactive toward electrophilic palladation at the para-positions. A wide range of synthetically important and advanced indoline analogues are selectively functionalized at the meta-positions.

  DOI：

  10.1021/ja505737x
• 作为产物：
  描述：

  邻甲氧基苯乙腈 在 氯磺酸 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.0h， 生成 tert-butyl 9-((3-(4-cyano-2,6-dimethylheptan-4-yl)-4-methoxyphenyl)sulfonyl)-1-propyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate
  参考文献：
  名称：

  Pd(II)-Catalyzed meta-C–H Olefination, Arylation, and Acetoxylation of Indolines Using a U-Shaped Template

  摘要：

  meta-C-H olefination, arylation, and acetoxylation of indolines have been developed using nitrile-containing templates. The combination of a monoprotected amino acid ligand and the nitrile template attached at the indolinyl nitrogen via a sulfonamide linkage is crucial for the meta-selective C-H fiunctionalization of electron-rich indolines that are otherwise highly reactive toward electrophilic palladation at the para-positions. A wide range of synthetically important and advanced indoline analogues are selectively functionalized at the meta-positions.

  DOI：

  10.1021/ja505737x