(S)-2-bromo-3-(1-(methoxy(methyl)amino)-1-oxopropan-2-yloxy)-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate | 1159795-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-2-bromo-3-(1-(methoxy(methyl)amino)-1-oxopropan-2-yloxy)-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate
• 英文别名: [2-bromo-3-[(2S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]oxy-4-[2-(2-trimethylsilylethoxy)ethyl]phenyl] tert-butyl carbonate
• CAS: 1159795-88-6
• 化学式: C₂₃H₃₈BrNO₇Si
• 分子量: 548.547
• InChiKey: DMHFMKGIEYVHQJ-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-bromo-3-(1-(methoxy(methyl)amino)-1-oxopropan-2-yloxy)-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate 在 lithium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 以95%的产率得到(S)-2-(2-bromo-3-hydroxy-6-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenoxy)-N-methoxy-N-methylpropanamide
  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：

  2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate 、 (R)-2-hydroxy-N-methoxy-N-methylpropanamide 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， 反应 24.0h， 以87%的产率得到(S)-2-bromo-3-(1-(methoxy(methyl)amino)-1-oxopropan-2-yloxy)-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate
  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.