trans-4,5-diphenyl-2-methoxy-2-methyl-1,3-dioxolane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-4,5-diphenyl-2-methoxy-2-methyl-1,3-dioxolane
• 英文别名: (4S,5S)-2-methoxy-2-methyl-4,5-diphenyl-1,3-dioxolane
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: IBSIFLQLQSKVLD-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-4,5-diphenyl-2-methoxy-2-methyl-1,3-dioxolane 在 水 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 rel-(1R,2R)-2-hydroxy-1,2-diphenylethyl acetate
  参考文献：
  名称：

  vic-二醇的酸性，选择性单酰化。

  摘要：

  DOI：

  10.1021/jo960081a
• 作为产物：
  描述：

  原乙酸三甲酯 、 (S,S)-(-)-氢化苯偶姻 在 硫酸 作用下， 以 苯 为溶剂， 以70%的产率得到trans-4,5-diphenyl-2-methoxy-2-methyl-1,3-dioxolane
  参考文献：
  名称：

  Chiral orthoesters in organic synthesis: Novel reagents for the enantioselective acylation of silylenolethers

  摘要：

  Dialkyl trans-2-alkoxy-2-alkyl-1,3-dioxolan-4,5-dicarboxylates and the corresponding N,N,N,N-tetramethyl-4,5-diamides have been prepared respectively from dialkyl tartrates or tartaric acid diamides. They smoothly reacted with silylenolethers in the presence of Lewis acids to give enantiomerically enriched (up to 90% d.e.) monoprotected 1,3-diketones. A dramatic dependence of the stereochemical outcome from the configuration of the enolic double bond of 4 has been observed. The products can be stereoselectively reduced to give configurationally defined monoprotected 3-ketols.

  DOI：

  10.1016/s0040-4020(01)90792-6

文献信息

• Acidic, Selective Monoacylation of <i>vic</i>-Diols
  作者：Masato Oikawa、Akira Wada、Fumiaki Okazaki、Shoichi Kusumoto

  DOI：10.1021/jo960081a

  日期：1996.1.1
• Chiral orthoesters in organic synthesis: Novel reagents for the enantioselective acylation of silylenolethers
  作者：Luigi Longobardo、Giovanna Mobbili、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1016/s0040-4020(01)90792-6

  日期：1992.1

  Dialkyl trans-2-alkoxy-2-alkyl-1,3-dioxolan-4,5-dicarboxylates and the corresponding N,N,N,N-tetramethyl-4,5-diamides have been prepared respectively from dialkyl tartrates or tartaric acid diamides. They smoothly reacted with silylenolethers in the presence of Lewis acids to give enantiomerically enriched (up to 90% d.e.) monoprotected 1,3-diketones. A dramatic dependence of the stereochemical outcome from the configuration of the enolic double bond of 4 has been observed. The products can be stereoselectively reduced to give configurationally defined monoprotected 3-ketols.