1,3-bis(diphenylphosphino)-1H-indole | 1430885-76-9

• 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: 1,3-bis(diphenylphosphino)-1H-indole
• 英文别名: (1-Diphenylphosphanylindol-3-yl)-diphenylphosphane
• CAS: 1430885-76-9
• 化学式: C₃₂H₂₅NP₂
• 分子量: 485.505
• InChiKey: BNSHEGKCOBMORB-UHFFFAOYSA-N

物化性质

• 沸点：
  627.3±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-bis(diphenylphosphino)-1H-indole 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 48.08h， 生成
  参考文献：
  名称：

  Influence of the Ligand Backbone in Pincer Complexes: Indenediide-, Indolyl-, and Indenyl-Based SCS Palladium Complexes

  摘要：

  A new pincer ligand featuring an indolyl backbone was prepared and coordinated to palladium. The properties of related indenediide-, indenyl-, and indolyl-based complexes have been compared by spectroscopic and structural means. Modulation of the ligand backbone was shown to significantly influence the electron density at Pd. Its impact on catalytic performance has been illustrated in the Pd-catalyzed imine allylation. The higher the electron density at Pd, the more active the SCS pincer complex.

  DOI：

  10.1021/om400464j
• 作为产物：
  描述：

  吲哚 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 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
• 作为试剂：
  描述：

  1-萘硼酸 、 对氯苯乙酮 在 双(乙腈)氯化钯(II) 、 1,3-bis(diphenylphosphino)-1H-indole 、 sodium hydroxide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 8.0h， 以81%的产率得到1-(4-naphthalen-1-ylphenyl)ethanone
  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