1-(tert-butyldimethylsilyl)-3-(diphenylphosphino)-1H-indole | 1430885-74-7

• 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: 1-(tert-butyldimethylsilyl)-3-(diphenylphosphino)-1H-indole
• CAS: 1430885-74-7
• 化学式: C₂₆H₃₀NPSi
• 分子量: 415.59
• InChiKey: IKHYZMBMCNIUIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  4.93
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldimethylsilyl)-3-(diphenylphosphino)-1H-indole 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 1,3-bis(diphenylphosphino)-1H-indole
  参考文献：
  名称：

  3-Indolylphosphines as ligand for palladium in Suzuki–Miyaura coupling reaction of chloroarenes: substituent effects

  摘要：

  The ligand 1,3-bis(diphenylphosphino)-1H-indole, L1 with palladium promotes Suzuki-Miyaura coupling reaction of chloroarenes and benzyl chlorides with arylboronic acids. Structural modification of L1 established that the phosphine group at C-3 position of indole was crucial to catalysis and its efficacy depended on the nature of the N-substituent. P-31 chemical shift values of the substituted indolylphosphines appear to show a correlation with observed trend in catalytic efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.030
• 作为产物：
  描述：

  N-tert-butyldimethylsilylindole 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-(tert-butyldimethylsilyl)-3-(diphenylphosphino)-1H-indole
  参考文献：
  名称：

  3-Indolylphosphines as ligand for palladium in Suzuki–Miyaura coupling reaction of chloroarenes: substituent effects

  摘要：

  The ligand 1,3-bis(diphenylphosphino)-1H-indole, L1 with palladium promotes Suzuki-Miyaura coupling reaction of chloroarenes and benzyl chlorides with arylboronic acids. Structural modification of L1 established that the phosphine group at C-3 position of indole was crucial to catalysis and its efficacy depended on the nature of the N-substituent. P-31 chemical shift values of the substituted indolylphosphines appear to show a correlation with observed trend in catalytic efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.030
• 作为试剂：
  描述：

  硝基氯苯 、 苯硼酸 在 双(乙腈)氯化钯(II) 、 1-(tert-butyldimethylsilyl)-3-(diphenylphosphino)-1H-indole 、 sodium hydroxide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 以97%的产率得到2-硝基联苯
  参考文献：
  名称：

  3-Indolylphosphines as ligand for palladium in Suzuki–Miyaura coupling reaction of chloroarenes: substituent effects

  摘要：

  The ligand 1,3-bis(diphenylphosphino)-1H-indole, L1 with palladium promotes Suzuki-Miyaura coupling reaction of chloroarenes and benzyl chlorides with arylboronic acids. Structural modification of L1 established that the phosphine group at C-3 position of indole was crucial to catalysis and its efficacy depended on the nature of the N-substituent. P-31 chemical shift values of the substituted indolylphosphines appear to show a correlation with observed trend in catalytic efficiency. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.030