1-diphenylthiophosphoryl-2-thioxo-2-phenyl-1,2λ⁵-azaphospholane | 1428772-04-6

• 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-diphenylthiophosphoryl-2-thioxo-2-phenyl-1,2λ⁵-azaphospholane
• 英文别名: Diphenyl-(2-phenyl-2-sulfidoazaphospholidin-2-ium-1-yl)-sulfidophosphanium；diphenyl-(2-phenyl-2-sulfidoazaphospholidin-2-ium-1-yl)-sulfidophosphanium
• CAS: 1428772-04-6
• 化学式: C₂₁H₂₁NP₂S₂
• 分子量: 413.484
• InChiKey: OYNWOOFDRPJEPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  5.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二(氰基苯)二氯化钯 、 1-diphenylthiophosphoryl-2-thioxo-2-phenyl-1,2λ⁵-azaphospholane 以 乙腈 为溶剂， 反应 48.0h， 以75%的产率得到
  参考文献：
  名称：

  Pd(II) and Pt(II) complexes of cyclic bidentate (S)PNP(S) ligands: Synthesis, structure and catalytic activity in the Suzuki reaction

  摘要：

  The synthetic approach to the novel cyclic (S)PNP(S) ligands PhP(S)(CH2)(3)NP(S)(R)(PH) (5a-c, R = EtO, Me, Ph), i.e. 1-thiophosphoryl-2-thioxo-1,2-azaphospholanes having different surrounding at the exocyclic phosphorus atom, has been developed. Compounds bearing two asymmetric phosphorus atoms were obtained as individual(R*,R*)- and (R*, S*)-diastereomers. Reacting with (PhCN)(2)MCl2 (M = Pd, Pt) in MeCN under ambient conditions the ligands readily form complexes MLCl2 [6a-c (M = Pd), 7b (M = Pt)] via bidentate chelating coordination mode. The structures and stereochemistry both of the ligands and their complexes were confirmed by IR, multinuclear NMR and X-ray diffraction study. The palladium complexes demonstrated high activity as precatalysts for the Suzuki cross-coupling reaction, which was found to increase in the series 6a < 6b < 6c. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.11.005
• 作为产物：
  描述：

  2-Phenyl-[1,2]azaphospholidine 2-oxide 在 劳森试剂 、 sulfur 、 三乙胺 作用下， 以 氯仿 、 甲苯 、 苯 为溶剂， 反应 7.0h， 生成 1-diphenylthiophosphoryl-2-thioxo-2-phenyl-1,2λ⁵-azaphospholane
  参考文献：
  名称：

  Pd(II) and Pt(II) complexes of cyclic bidentate (S)PNP(S) ligands: Synthesis, structure and catalytic activity in the Suzuki reaction

  摘要：

  The synthetic approach to the novel cyclic (S)PNP(S) ligands PhP(S)(CH2)(3)NP(S)(R)(PH) (5a-c, R = EtO, Me, Ph), i.e. 1-thiophosphoryl-2-thioxo-1,2-azaphospholanes having different surrounding at the exocyclic phosphorus atom, has been developed. Compounds bearing two asymmetric phosphorus atoms were obtained as individual(R*,R*)- and (R*, S*)-diastereomers. Reacting with (PhCN)(2)MCl2 (M = Pd, Pt) in MeCN under ambient conditions the ligands readily form complexes MLCl2 [6a-c (M = Pd), 7b (M = Pt)] via bidentate chelating coordination mode. The structures and stereochemistry both of the ligands and their complexes were confirmed by IR, multinuclear NMR and X-ray diffraction study. The palladium complexes demonstrated high activity as precatalysts for the Suzuki cross-coupling reaction, which was found to increase in the series 6a < 6b < 6c. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.11.005