1-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-2,3-dihydro-1H-indole | 623462-14-6

• 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-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-2,3-dihydro-1H-indole
• 英文别名: 1-(2-diphenylphosphoryl-6-methoxyphenyl)-2,3-dihydroindole
• CAS: 623462-14-6
• 化学式: C₂₇H₂₄NO₂P
• 分子量: 425.467
• InChiKey: AQMGAOUBORZSKB-UHFFFAOYSA-N

物化性质

• 沸点：
  637.5±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-2,3-dihydro-1H-indole 在 Chiralcel(R) OJ 、 三氯硅烷 、 三乙胺 作用下， 生成 1-(2-Diphenylphosphanyl-6-methoxy-phenyl)-2,3-dihydro-1H-indole
  参考文献：
  名称：

  A C(aryl)N(amine) bond atropisomeric aminophosphine: preparation and use as a ligand in a catalytic asymmetric allylic alkylation

  摘要：

  The existence of 3 as a pair of stable atropisomers has been demonstrated analytically through chiral phase LC-CD investigations. Resolution of 3d was achieved by preparative chiral HPLC. Finally, the ability of the first C(aryl)-N(amine) axially chiral phosphine ligand 3d is demonstrated in a catalytic asymmetric reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00545-7
• 作为产物：
  描述：

  indoline lithium salt 、 2,3-dimethoxyphenyldiphenylphosphine oxide 生成 1-[2-(Diphenyl-phosphinoyl)-6-methoxy-phenyl]-2,3-dihydro-1H-indole
  参考文献：
  名称：

  A C(aryl)N(amine) bond atropisomeric aminophosphine: preparation and use as a ligand in a catalytic asymmetric allylic alkylation

  摘要：

  The existence of 3 as a pair of stable atropisomers has been demonstrated analytically through chiral phase LC-CD investigations. Resolution of 3d was achieved by preparative chiral HPLC. Finally, the ability of the first C(aryl)-N(amine) axially chiral phosphine ligand 3d is demonstrated in a catalytic asymmetric reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00545-7

文献信息

• N-Aryl indole-derived C–N bond axially chiral phosphine ligands: synthesis and application in palladium-catalyzed asymmetric allylic alkylation
  作者：Takashi Mino、Shingo Komatsu、Kazuya Wakui、Haruka Yamada、Hiroaki Saotome、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.tetasy.2010.03.039

  日期：2010.4

  N-Aryl indole-derived C–N bond axially chiral phosphine ligands 2a–c were obtained by DDQ oxidation of N-aryl indoline-derived phosphine oxide followed by silane reduction. Resolution of C–N bond atropisomers was achieved by chiral HPLC. The investigation of the rotation barrier for the C–N bond axial stability of phosphines and the determination of the absolute configuration of 2c are described. Finally

  N-芳基吲哚衍生的C–N键轴向手性膦配体2a – c是通过N-芳基吲哚啉衍生的氧化膦的DDQ氧化，然后进行硅烷还原而获得的。通过手性HPLC可实现C–N键阻转异构体的拆分。描述了对膦的C–N键轴向稳定性的旋转势垒的研究以及2c的绝对构型的确定。最后，在钯催化的不对称烯丙基烷基化反应中（至多99％ee）证明了手性配体2c的能力。