(2S,4aR,8aR)-2-phenyl-4,4a-dihydropyrano[3,2-d][1,3]dioxin-6(8aH)-one | 1004994-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (2S,4aR,8aR)-2-phenyl-4,4a-dihydropyrano[3,2-d][1,3]dioxin-6(8aH)-one
• 英文别名: (2S,4aR,8aR)-2-phenyl-4a,8a-dihydro-4H-pyrano[3,2-d][1,3]dioxin-6-one
• CAS: 1004994-82-4
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: KJUKTXWIYAAMIG-WZRBSPASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯氧基磷基乙酸乙酯 、 2,4-O-benzylidene-D-threose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(2S,4aR,8aR)-2-phenyl-4,4a-dihydropyrano[3,2-d][1,3]dioxin-6(8aH)-one
  参考文献：
  名称：

  A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon

  摘要：

  A multi-gram synthesis of a substituted alpha,beta-unsaturated delta-lactone synthon, 1, was developed from commercially available D-galactose. The use of a Horner-Wadsworth-Emmons reaction was able to furnish, with Z selectivity, the enone ester that spontaneously lactonised to provide enantiomerically pure 1. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.141

文献信息

• A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon
  作者：Benjamin E. Stephens、Fei Liu

  DOI：10.1016/j.tetlet.2007.10.141

  日期：2007.12

  A multi-gram synthesis of a substituted alpha,beta-unsaturated delta-lactone synthon, 1, was developed from commercially available D-galactose. The use of a Horner-Wadsworth-Emmons reaction was able to furnish, with Z selectivity, the enone ester that spontaneously lactonised to provide enantiomerically pure 1. (C) 2007 Elsevier Ltd. All rights reserved.