4-bromo-1,1-dimethoxypentane | 89940-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-bromo-1,1-dimethoxypentane
• 英文别名: 4-bromo-1,1-dimethoxy-pentane；Dimethylacetal des 4-Brom-pentanal-(1)
• CAS: 89940-00-1
• 化学式: C₇H₁₅BrO₂
• 分子量: 211.099
• InChiKey: KYWXRBCOTRNSNO-UHFFFAOYSA-N

物化性质

• 沸点：
  198.8±30.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-1,1-dimethoxypentane 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 florisil 、 正丁基锂 、 lithium 、 对甲苯磺酸 、 pyridinium chlorochromate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 7.33h， 生成 (3aα,5aβ,8β,8aβ)-1,2,3a,5,5a,6,7,8-octahydro-2,2,8-trimethylcyclopentapentalene-3,4-dione
  参考文献：
  名称：

  Nickel-Catalyzed Cyclizations of Enoate Equivalents:  Application to the Synthesis of Angular Triquinanes

  摘要：

  Unsaturated acyloxazolidinones and alpha'-silyloxy enones were found to be effective substrates in nickel-catalyzed organozinc-promoted cyclizations. Both groups served as convenient enoate equivalents, whereas methyl enoates themselves were inefficient substrates. A five-step procedure for the conversion of dimethylcyclopentenone into a highly functionalized angular triquinane was developed utilizing this observation. The key step of the procedure involves a nickel-catalyzed reductive cyclization/Dieckmann condensation sequence involving a cyclic enone tethered to an unsaturated acyloxazolidinone or alpha'-silyloxy enone. The method was applied ina formal synthesis of pentalenene, pentalenic acid, and deoxypentalenic acid.

  DOI：

  10.1021/jo9908389

文献信息

• Obol'nikova,E.A.; Samokhvalov,G.I., Journal of general chemistry of the USSR, 1963, vol. 33, # 6, p. 1809 - 1812
  作者：Obol'nikova,E.A.、Samokhvalov,G.I.

  DOI：——

  日期：——
• Nickel-Catalyzed Cyclizations of Enoate Equivalents:  Application to the Synthesis of Angular Triquinanes
  作者：Jeongbeob Seo、Hélène Fain、Jean-Baptiste Blanc、John Montgomery

  DOI：10.1021/jo9908389

  日期：1999.8.1

  Unsaturated acyloxazolidinones and alpha'-silyloxy enones were found to be effective substrates in nickel-catalyzed organozinc-promoted cyclizations. Both groups served as convenient enoate equivalents, whereas methyl enoates themselves were inefficient substrates. A five-step procedure for the conversion of dimethylcyclopentenone into a highly functionalized angular triquinane was developed utilizing this observation. The key step of the procedure involves a nickel-catalyzed reductive cyclization/Dieckmann condensation sequence involving a cyclic enone tethered to an unsaturated acyloxazolidinone or alpha'-silyloxy enone. The method was applied ina formal synthesis of pentalenene, pentalenic acid, and deoxypentalenic acid.