(+)-(R,R)-1,1'-bis(diphenylhydroxymethyl)-2,2'-dimethyl-ferrocene | 223386-11-6

• 分子结构分类: 有机化合物
• 英文名称: (+)-(R,R)-1,1'-bis(diphenylhydroxymethyl)-2,2'-dimethyl-ferrocene
• 英文别名: iron(2+);(5-methylcyclopenta-1,3-dien-1-yl)-diphenylmethanol
• CAS: 223386-11-6
• 化学式: C₃₈H₃₄FeO₂
• 分子量: 578.534
• InChiKey: BKUMNEFPGXDSST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  titanium(IV) isopropylate 、 (+)-(R,R)-1,1'-bis(diphenylhydroxymethyl)-2,2'-dimethyl-ferrocene 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Achiral and planar chiral ferrocene diols: preparation and complexation with titanium(IV)

  摘要：

  Achiral ferrocene diol, 1,1'-bis(diphenylhydroxymethyl)ferrocene 5, was prepared by the direct dilithiation of ferrocene with n-butyllithium in the presence of TMEDA followed by treatment with benzophenone, while the first chiral C-2-symmetric ferrocene diol possessing only the planar chirality, (+)-(R,R)-1,1'-bis(diphenylhydroxymethyl)-2,2'-dimethylferrocene 6, was prepared from (+)-(R,R)-1,1'-bis(oxazolinyl)-2,2'-dimethylferrocene 1b by the transformation of the oxazoline moieties. It was shown that diols 5 and 6 can form 1:1 complexes with tetraisopropyl titanate with ease. The X-ray crystal structure analysis of 5 with an intramolecular hydrogen-bonding showed that the phenyl groups in the molecule occupy quasi-axial and quasi-equatorial positions and these structures can be taken as the models of the titanium complexes of ferrocene diols. As a preliminary experiment, the titanium-catalyzed hydrosilylation of a ketone with 6 has also been carried out. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00930-9
• 作为产物：
  描述：

  溴苯 、 (+)-(R,R)-2,2'-dimethyl-1,1'-ferrocenedicarboxylic acid dimethyl ester 在 magnesium 作用下， 以 乙醚 为溶剂， 以65%的产率得到(+)-(R,R)-1,1'-bis(diphenylhydroxymethyl)-2,2'-dimethyl-ferrocene
  参考文献：
  名称：

  Achiral and planar chiral ferrocene diols: preparation and complexation with titanium(IV)

  摘要：

  Achiral ferrocene diol, 1,1'-bis(diphenylhydroxymethyl)ferrocene 5, was prepared by the direct dilithiation of ferrocene with n-butyllithium in the presence of TMEDA followed by treatment with benzophenone, while the first chiral C-2-symmetric ferrocene diol possessing only the planar chirality, (+)-(R,R)-1,1'-bis(diphenylhydroxymethyl)-2,2'-dimethylferrocene 6, was prepared from (+)-(R,R)-1,1'-bis(oxazolinyl)-2,2'-dimethylferrocene 1b by the transformation of the oxazoline moieties. It was shown that diols 5 and 6 can form 1:1 complexes with tetraisopropyl titanate with ease. The X-ray crystal structure analysis of 5 with an intramolecular hydrogen-bonding showed that the phenyl groups in the molecule occupy quasi-axial and quasi-equatorial positions and these structures can be taken as the models of the titanium complexes of ferrocene diols. As a preliminary experiment, the titanium-catalyzed hydrosilylation of a ketone with 6 has also been carried out. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00930-9