(Z)-2-bromo-3-(trimethylsilyl)propen-1-ol | 147727-40-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (Z)-2-bromo-3-(trimethylsilyl)propen-1-ol
• 英文别名: (Z)-2-bromo-3-trimethylsilylprop-2-en-1-ol
• CAS: 147727-40-0
• 化学式: C₆H₁₃BrOSi
• 分子量: 209.158
• InChiKey: SRQRUBRNDRETAR-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-bromo-3-(trimethylsilyl)propen-1-ol 在 咪唑 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.25h， 生成 (E)-1-(Trimethylsilyl)-2-(siloxymethyl)-1,3-butadiene
  参考文献：
  名称：

  Synthesis of (E)- and(Z)-1-(Trimethylsilyl)-2-(siloxymethyl)-1,3-butadienes: Versatile Building Blocks for Diels-Alder Cycloadditions Including an Approach toward Taxoids

  摘要：

  The synthesis of the E- and Z-substituted 1,3-butadienes 5 and 12 and their halodesilylation products 13-16, via Pd(0) mediated coupling of functionalized alkenes of defined stereochemistry, is described.

  DOI：

  10.1021/jo00098a007
• 作为产物：
  描述：

  (Z)-2-bromo-3-trimethylsilyl-2-propenal 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.25h， 以78%的产率得到(Z)-2-bromo-3-(trimethylsilyl)propen-1-ol
  参考文献：
  名称：

  An intramolecular cyclization approach to optically active cyclopentenyl bromides

  摘要：

  The two antipodes of 1-bromo-3,3-dimethyl-4-[(tert-butyldimethylsilyl)oxy]cyclopentene, the dextrorotatory form of which (1) is regarded as a potential synthetic precursor to kalmanol, have been prepared in a state of high enantiomeric purity from propargyl alcohol. The key steps in the abbreviated synthetic pathway involve the bromination-dehydrobromination of aldehyde 12 to give 7, the conversion of alcohol 13 to the hydroxyl-substituted bromocyclopentene 18 by a novel tandem Claisen-Sakurai reaction sequence, and efficient enzymatic resolution of 18 via its chloroacetate ester. The absolute configurational assignments are based on H-1 NMR analyses of the (R)- and (S)-MTPA esters of (-)-20.

  DOI：

  10.1021/jo00062a011

文献信息

• Synthesis of (E)- and(Z)-1-(Trimethylsilyl)-2-(siloxymethyl)-1,3-butadienes: Versatile Building Blocks for Diels-Alder Cycloadditions Including an Approach toward Taxoids
  作者：Timothy Wong、Miguel A. Romero、Alex G. Fallis

  DOI：10.1021/jo00098a007

  日期：1994.9

  The synthesis of the E- and Z-substituted 1,3-butadienes 5 and 12 and their halodesilylation products 13-16, via Pd(0) mediated coupling of functionalized alkenes of defined stereochemistry, is described.
• An intramolecular cyclization approach to optically active cyclopentenyl bromides
  作者：Stephane Borrelly、Leo A. Paquette

  DOI：10.1021/jo00062a011

  日期：1993.5

  The two antipodes of 1-bromo-3,3-dimethyl-4-[(tert-butyldimethylsilyl)oxy]cyclopentene, the dextrorotatory form of which (1) is regarded as a potential synthetic precursor to kalmanol, have been prepared in a state of high enantiomeric purity from propargyl alcohol. The key steps in the abbreviated synthetic pathway involve the bromination-dehydrobromination of aldehyde 12 to give 7, the conversion of alcohol 13 to the hydroxyl-substituted bromocyclopentene 18 by a novel tandem Claisen-Sakurai reaction sequence, and efficient enzymatic resolution of 18 via its chloroacetate ester. The absolute configurational assignments are based on H-1 NMR analyses of the (R)- and (S)-MTPA esters of (-)-20.