1,1'-bis(dimethylaminomethyl)-2,2'-bis-diphenylphosphino<3,3'>-biindolyl | 175022-66-9

• 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: 1,1'-bis(dimethylaminomethyl)-2,2'-bis-diphenylphosphino<3,3'>-biindolyl
• CAS: 175022-66-9；175022-68-1
• 化学式: C₄₆H₄₄N₄P₂
• 分子量: 714.83
• InChiKey: NQZTYSHIVWHUSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  52.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  16.34
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,1'-bis(dimethylaminomethyl)-2,2'-bis-diphenylphosphino<3,3'>-biindolyl 在 六氟磷酸钾 、 chloropalladium complex with (R)-N,N-dimethyl-1'-(1-naphthyl)ethylamine 、 乙基二苯基膦 作用下， 生成 (S)-2,2'-bis-diphenylphosphino<3,3'>biindolyl
  参考文献：
  名称：

  Synthesis and resolution of 2,2'-bis-diphenylphosphino [3,3']biindolyl ; a new atropisomeric ligand for transition metal catalysis

  摘要：

  A synthesis of the title ligand is described in which the key step is the-dilithiation of 1,1'-bis(dimethylaminomethyl)-3,3'-biindolyl and electrophilic trapping with Cl(P)Ph(2). Concomitant N-deprotection and resolution with bis[(R)-dimethyl(1-(1-naphthyl) ethylaminato-C-2,N)palladium chloride] led to selective recovery of the S-enantiomer. The N-dimethylaminomethyl-substituted biindolyl,but not the parent compound, showed strongly second-order behaviour for C-13 NMR peaks in the region of the phosphorus atom due to a desymmetrising C-13-induced isotope shift of the P-31 resonance.

  DOI：

  10.1016/0957-4166(95)00447-5
• 作为产物：
  描述：

  1H,1'H-[3,3']biindolyl 在 正丁基锂 、 乙二醇二甲醚 、 三乙胺 作用下， 反应 26.0h， 生成 1,1'-bis(dimethylaminomethyl)-2,2'-bis-diphenylphosphino<3,3'>-biindolyl
  参考文献：
  名称：

  Synthesis and resolution of 2,2'-bis-diphenylphosphino [3,3']biindolyl ; a new atropisomeric ligand for transition metal catalysis

  摘要：

  A synthesis of the title ligand is described in which the key step is the-dilithiation of 1,1'-bis(dimethylaminomethyl)-3,3'-biindolyl and electrophilic trapping with Cl(P)Ph(2). Concomitant N-deprotection and resolution with bis[(R)-dimethyl(1-(1-naphthyl) ethylaminato-C-2,N)palladium chloride] led to selective recovery of the S-enantiomer. The N-dimethylaminomethyl-substituted biindolyl,but not the parent compound, showed strongly second-order behaviour for C-13 NMR peaks in the region of the phosphorus atom due to a desymmetrising C-13-induced isotope shift of the P-31 resonance.

  DOI：

  10.1016/0957-4166(95)00447-5