2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate | 1159795-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate
• 英文别名: [2-Bromo-3-hydroxy-4-[2-(2-trimethylsilylethoxy)ethyl]phenyl] tert-butyl carbonate
• CAS: 1159795-87-5
• 化学式: C₁₈H₂₉BrO₅Si
• 分子量: 433.415
• InChiKey: ROYBUMLFQNDCCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-bromo-3-hydroxy-4-(2-(2-(trimethylsilyl)ethoxy)ethyl)phenyl tert-butyl carbonate 、 (S)-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 12.0h， 生成
  参考文献：
  名称：

  Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones

  摘要：

  The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.05.041
• 作为产物：
  描述：

  trimethyl(2-((tributylstannyl)methoxy)ethyl)silane 、 carbonic acid 2-bromo-3-tert-butoxycarbonyloxy-6-formyl-phenyl ester tert-butyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以68%的产率得到2-bromo-3-hydroxy-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.
• Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones
  作者：Todd A. Wenderski、Christophe Hoarau、Lupe Mejorado、Thomas R.R. Pettus

  DOI：10.1016/j.tet.2010.05.041

  日期：2010.7

  The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts. Published by Elsevier Ltd.