2-((diphenylphosphino)methyl)quinolin-8-ol acetate | 171735-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-((diphenylphosphino)methyl)quinolin-8-ol acetate
• 英文别名: [2-(Diphenylphosphanylmethyl)quinolin-8-yl] acetate
• CAS: 171735-75-4
• 化学式: C₂₄H₂₀NO₂P
• 分子量: 385.402
• InChiKey: QAKSHPKALQMWNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  di-μ-chloro-bis[bis(cyclo-octene)rhodium] 、 2-((diphenylphosphino)methyl)quinolin-8-ol acetate 以 苯 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Facile Oxidative Addition of Rhodium(I) to the Acyl-Oxygen Bond of 2-((Diphenylphosphino)methyl)quinolin-8-ol Acetate

  摘要：

  Conversion of 2-methylquinolin-8-ol to 2-((diphenylphosphino)methyl)quinolin-8-ol (2; 61% overall yield) by protection, lithiation, phosphinylation, and deprotection is described. The corresponding acetate 3 reacts with the dimer [(cyclooctene)(2)Rh(mu-Cl)](2) (4) in a molar ratio of 4:1 within minutes at ambient temperatures. A single Rh bis(phosphine) acyl complex (13a) is obtained, whereas three diastereomers are possible. In 13a, one molecule of 3 is a spectator ligand coordinated through P, whereas a second molecule of 3 has undergone unprecedentedly rapid oxidative addition to the acyl-oxygen bond, providing a COCH3 ligand and the P,O,N-coordinated anion of 2. The stereochemistry of 13a (COCH3 and CI mutually trans) was determined by coupling information and 2D NMR experiments. The COCH3 ligand of 13a is unaffected by PhCH(2)NH(2) (room temperature, 6 h), and 13a is essentially unchanged after 7 days at 120 degrees C in C6D6. Interactions of 2 and 4 or its Ir analog 5 in a molar ratio of 4:1 give metal hydride complexes as single diastereomers, from addition of the O-H bond to the metal.

  DOI：

  10.1021/om00011a039