(+/-)-1-bromo-3,3-dimethylcyclopenten-4-ol | 147727-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1-bromo-3,3-dimethylcyclopenten-4-ol
• 英文别名: 4-Bromo-2,2-dimethylcyclopent-3-en-1-ol
• CAS: 147727-42-2
• 化学式: C₇H₁₁BrO
• 分子量: 191.068
• InChiKey: HPXNZCMIZMTFKT-UHFFFAOYSA-N

物化性质

• 沸点：
  224.1±40.0 °C(predicted)
• 密度：
  1.472±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (+/-)-1-bromo-3,3-dimethylcyclopenten-4-ol 在 吡啶 、 咪唑 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 1-bromo-3,3-dimethyl-4-<(tert-butyldimethylsilyl)oxy>cyclopentene
  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：

  (4-Bromo-2,2-dimethyl-cyclopent-3-enyloxy)-trimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (+/-)-1-bromo-3,3-dimethylcyclopenten-4-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