8-(4,8-di-tert-butyl-1,11-dimethoxy-5,7-dioxa-6-phospha-dibenzo[a,c]cyclohepten-6-yloxy)quinoline | 499199-27-8

• 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: 8-(4,8-di-tert-butyl-1,11-dimethoxy-5,7-dioxa-6-phospha-dibenzo[a,c]cyclohepten-6-yloxy)quinoline
• 英文别名: 8-(4,8-Ditert-butyl-2,10-dimethoxybenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxyquinoline
• CAS: 499199-27-8
• 化学式: C₃₁H₃₄NO₅P
• 分子量: 531.588
• InChiKey: BNFRYOZEOBAOOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二(氰基苯)二氯化钯 、 8-(4,8-di-tert-butyl-1,11-dimethoxy-5,7-dioxa-6-phospha-dibenzo[a,c]cyclohepten-6-yloxy)quinoline 以 甲苯 为溶剂， 以74%的产率得到cis-[PdCl2(8-(4,8-di-tert-butyl-1,11-dimethoxy-5,7-dioxa-6-phospha-dibenzo[a,c]cyclohepten-6-yloxy)-quinoline)]
  参考文献：
  名称：

  Synthesis of Phosphonito,N and Phosphito,N ligands based on quinolines and (R)-binaphthol or substituted biphenol and of their rhodium(I), palladium(II) and platinum(II) complexes

  摘要：

  The new Phosphonito,N ligands 8-(4,8-di-tert-butyl-1,11-dimethoxy-5,7-dioxa-6-phospha-dibenzo[a,c]cyclohepten-6-yl)-quinoline (2a), and (R)-8-(3,5-dioxa-4-phospha-cyclohepta-[2,1-a;3,4-a']dinaphthalen-4-yl)-quinoline ((R)-2b), were readily prepared starting from 8-(bis-diethylamino-phosphine)-quinoline (1), as a key intermediate, and 2,2'-dihydroxy-5,5'-dimethoxy-3,3-di-tert-butylbiphenyl or (R)-binaphthol, respectively. The Phosphito,N ligand, 8-(4,8-di-tert-butyl-1,11-dimethoxy-5,7-dioxa-6-phosphadibenzo[a,c]cyclohepten-6-yloxy)-quinoline (3a), was obtained by reacting equimolar amounts of 8-hydroxyquinoline and the phosphorochloridite derived from 3,3'-di-tert-butyl-2,2'-dihydroxy-5,5'-dimethoxybiphenyl, in toluene in the presence of NEt3. The corresponding Phosphito,N-ligand, 8-(3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yloxy)-quinoline (R)-(3b), was obtained similarly using the phosphorochloridite derived from (R)-binaphthol. A systematic study of the coordination abilities of 2-3 to rhodium(l), palladium(II) and platinum(II) precursors has been carried out. Crystal structures of the complexes [Pt(3a)I-2] (7a), and [Pd(2a)Cl-2] (8a), are reported. The reactions of the chiral ligands (R)-2b and (R)-3b with [Rh(acaC)(CO)(2)] lead to [Rh(acac)(R-2b)] (10), and [Rh(acac)(R-3b)] (11), respectively. Under hydroformylation conditions, displacement of the chiral ligands in both complexes 10 and 11 takes place, even in the presence of an excess of free ligand, leading to achiral hydrido-carbonyl rhodium complexes. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0020-1693(02)00849-6