5,5-diphenyl-2-diphenylmethyl-4-hydroxy-1,3-dioxolane | 1180511-14-1

• 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: 5,5-diphenyl-2-diphenylmethyl-4-hydroxy-1,3-dioxolane
• 英文别名: DDHDA；2-Benzhydryl-5,5-diphenyl-1,3-dioxolan-4-ol；2-benzhydryl-5,5-diphenyl-1,3-dioxolan-4-ol
• CAS: 1180511-14-1
• 化学式: C₂₈H₂₄O₃
• 分子量: 408.497
• InChiKey: ISKCMHFYBVABKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 5,5-diphenyl-2-diphenylmethyl-4-hydroxy-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of a novel sterically hindered chiral cyclic phosphoric acid derived from l-tartaric acid and application to the asymmetric catalytic Biginelli reaction

  摘要：

  A novel sterically hindered chiral cyclic phosphoric acid derived from L-tartaric acid was designed and synthesized based on highly regioselective cyclosulfitation of chiral 1,1,4,4-tetraphenylbutanetetraol. The asymmetric Biginelli reaction catalyzed by this newly synthesized chiral phosphoric acid was examined, and enantioselectivities up to 99% ee was obtained. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.11.014

文献信息

• Convenient access to sterically hindered C2 chiral 2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols: intramolecular selective 1,4-cyclocondensation of (2R,3R)- and (2S,3S)-1,1,4,4-tetraphenylbutanetetraols
  作者：Xiaoyun Hu、Zixing Shan、Xitian Peng、Zhen Li

  DOI：10.1016/j.tetasy.2009.10.005

  日期：2009.11

  Sterically hindered C-2 chiral (3R,4R)- and (3S,4S)-2,2,5,5-tetraphenyltetrahydrofuran-3,4-diols have been conveniently prepared in a very high yield via heterogeneous intramolecular selective 1,4-cyclocondensation of (2R,3R)- and (2S,3S)-1,1,4,4-tetraphenylbutanetetraol in concentrated hydrohalic acids, respectively. Preliminary examination of additives for the Barbas-List reaction showed that in certain cases, the hindered C-2 chiral tetrahydrofuran-3,4-diols were better chiral auxiliaries than enantiopure (R)- and (S)-1,1'-bi-2-naphthols. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of a novel sterically hindered chiral cyclic phosphoric acid derived from l-tartaric acid and application to the asymmetric catalytic Biginelli reaction
  作者：Xiaoyun Hu、Rui Zhang、Jinsheng Xie、Zhongqiang Zhou、Zixing Shan

  DOI：10.1016/j.tetasy.2016.11.014

  日期：2017.1

  A novel sterically hindered chiral cyclic phosphoric acid derived from L-tartaric acid was designed and synthesized based on highly regioselective cyclosulfitation of chiral 1,1,4,4-tetraphenylbutanetetraol. The asymmetric Biginelli reaction catalyzed by this newly synthesized chiral phosphoric acid was examined, and enantioselectivities up to 99% ee was obtained. (C) 2016 Elsevier Ltd. All rights reserved.