(1'S,3'S,7'S)-spiro[1,5-dihydro-2,4-benzodioxepine-3,5'-2,8-dioxatricyclo[5.3.0.01,3]decane] | 1159795-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1'S,3'S,7'S)-spiro[1,5-dihydro-2,4-benzodioxepine-3,5'-2,8-dioxatricyclo[5.3.0.01,3]decane]
• CAS: 1159795-98-8
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: JHRXLNTXUCCLMM-OFQRWUPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3a'S,4'R,7a'S)-1,3',3a',4',5,5',7',7a'-octahydro-2'H-spiro[benzo[e][1,3]dioxepine-3,6'-benzofuran]-3a',4'-diol 、 对硝基苯甲酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(1'S,3'S,7'S)-spiro[1,5-dihydro-2,4-benzodioxepine-3,5'-2,8-dioxatricyclo[5.3.0.01,3]decane]
  参考文献：
  名称：

  Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments

  摘要：

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.

  DOI：

  10.1021/jo900401k