1-(trimethylsilyl)-2-bromo-6-methyl-4-oxa-1,5-heptadiene | 147727-41-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 1-(trimethylsilyl)-2-bromo-6-methyl-4-oxa-1,5-heptadiene
• 英文别名: [(Z)-2-bromo-3-(2-methylprop-1-enoxy)prop-1-enyl]-trimethylsilane
• CAS: 147727-41-1
• 化学式: C₁₀H₁₉BrOSi
• 分子量: 263.25
• InChiKey: SKLNUCHPPLKVDC-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(trimethylsilyl)-2-bromo-6-methyl-4-oxa-1,5-heptadiene 在 氯化二乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4-Bromo-2,2-dimethyl-cyclopent-3-enyloxy)-trimethyl-silane
  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
• 作为产物：
  描述：

  (Z)-2-bromo-3-trimethylsilyl-2-propenal 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 72.25h， 生成 1-(trimethylsilyl)-2-bromo-6-methyl-4-oxa-1,5-heptadiene
  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

• 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.