(3S,8aR)-5-bromo-3-methyl-8a-(2-(2-(trimethylsilyl)ethoxy)ethyl)benzo[b][1,4]dioxin-2,6(3H,8aH)-dione | 1159795-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (3S,8aR)-5-bromo-3-methyl-8a-(2-(2-(trimethylsilyl)ethoxy)ethyl)benzo[b][1,4]dioxin-2,6(3H,8aH)-dione
• 英文别名: (2S,4aR)-8-bromo-2-methyl-4a-[2-(2-trimethylsilylethoxy)ethyl]-1,4-benzodioxine-3,7-dione
• CAS: 1159795-90-0
• 化学式: C₁₆H₂₃BrO₅Si
• 分子量: 403.345
• InChiKey: WCPAYCHIRXZFKV-ZBEGNZNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,8aR)-5-bromo-3-methyl-8a-(2-(2-(trimethylsilyl)ethoxy)ethyl)benzo[b][1,4]dioxin-2,6(3H,8aH)-dione 在 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 L-Selectride 、 水 、 rochelle salt 作用下， 以 正己烷 、 甲苯 、 四氢呋喃 为溶剂， 反应 0.16h， 以83%的产率得到(3S,4aS,5R,8aR)-5-bromo-3-methyl-8a-(2-(2-(trimethylsilyl)ethoxy)ethyl)-4a,5-dihydrobenzo[b][1,4]dioxin-2,6(3H,8aH)-dione
  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
• 作为产物：
  描述：

  (S)-2-(2-bromo-3-hydroxy-6-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenoxy)-N-methoxy-N-methylpropanamide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 硝基甲烷 为溶剂， 反应 0.25h， 以76%的产率得到(3S,8aR)-5-bromo-3-methyl-8a-(2-(2-(trimethylsilyl)ethoxy)ethyl)benzo[b][1,4]dioxin-2,6(3H,8aH)-dione
  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

文献信息

• Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments
  作者：Todd A. Wenderski、Shenlin Huang、Thomas R. R. Pettus

  DOI：10.1021/jo900401k

  日期：2009.6.5

  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.