2,3-O-cyclohexylidene-1,1,4,4-tetraphenylthreitol

• 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: 2,3-O-cyclohexylidene-1,1,4,4-tetraphenylthreitol
• 英文别名: [3-[Hydroxy(diphenyl)methyl]-1,4-dioxaspiro[4.5]decan-2-yl]-diphenylmethanol
• 化学式: C₃₄H₃₄O₄
• 分子量: 506.642
• InChiKey: BFEYEENPZZLVAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-O-cyclohexylidene-1,1,4,4-tetraphenylthreitol 、 维格列汀杂质 以 苯 为溶剂， 反应 2.0h， 以80%的产率得到(-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Second example for the heterocomplexation of chiral diols and complete disproportionation of enantiomers for non-racemic 2,3-O-cyclohexylidene-1,1,4,4-tetraphenylthreitols

  摘要：

  Inclusion complexation of a tricyclic dipeptide derived from (S)-proline toward several chiral diols was examined, and observed that inclusion complexation behavior depended strongly on the composition of diol. For 2,3-O-alkylidene-1,1,4,4-tetraphenylthreitols, the derivatives of cyclohexanone and acetone reacted with the dipeptide to generate a 1:2 inclusion complex; however, the former is achiroselective, affording the second heterocomplex known to date. Based on the heterocomplexation, complete disproportionation of enantiomers of non-racemic 2,3-O-cyclohexylidene-1,1,4,4-tetraphenylthreitol was successfully realized, leading to highly effective separation of the excess enantiomer from the racemate. On the other hand, inclusion complexation did not occur between the dipeptide and rac-pinanediol or (4R,5R)-4-diphenylhydroxymethyl-5-hydroxy-2,6,6-triphenyl-1,3,2-dioxaborolane. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.10.017

文献信息

• Second example for the heterocomplexation of chiral diols and complete disproportionation of enantiomers for non-racemic 2,3-O-cyclohexylidene-1,1,4,4-tetraphenylthreitols
  作者：Xiaoyun Hu、Zixing Shan、Wei Li

  DOI：10.1016/j.jfluchem.2009.10.017

  日期：2010.4

  Inclusion complexation of a tricyclic dipeptide derived from (S)-proline toward several chiral diols was examined, and observed that inclusion complexation behavior depended strongly on the composition of diol. For 2,3-O-alkylidene-1,1,4,4-tetraphenylthreitols, the derivatives of cyclohexanone and acetone reacted with the dipeptide to generate a 1:2 inclusion complex; however, the former is achiroselective, affording the second heterocomplex known to date. Based on the heterocomplexation, complete disproportionation of enantiomers of non-racemic 2,3-O-cyclohexylidene-1,1,4,4-tetraphenylthreitol was successfully realized, leading to highly effective separation of the excess enantiomer from the racemate. On the other hand, inclusion complexation did not occur between the dipeptide and rac-pinanediol or (4R,5R)-4-diphenylhydroxymethyl-5-hydroxy-2,6,6-triphenyl-1,3,2-dioxaborolane. (C) 2009 Elsevier B.V. All rights reserved.