1-(4,4-dimethoxybutyl)-4,4-dimethylcyclopent-2-en-1-ol | 244308-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4,4-dimethoxybutyl)-4,4-dimethylcyclopent-2-en-1-ol
• CAS: 244308-15-4
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: AFOHJNAISVRPQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4,4-dimethoxybutyl)-4,4-dimethylcyclopent-2-en-1-ol 在 4-二甲氨基吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 florisil 、 diethylzinc 、 对甲苯磺酸 、 pyridinium chlorochromate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 7.33h， 生成 (3aα,5aβ,8aβ)-1,2,3a,5,5a,6,7,8-octahydro-2,2-dimethylcyclopenta[c]pentalene-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
• 作为产物：
  描述：

  4,4-二甲基-2-环戊烯-1-酮 、 4-溴丁醛缩二甲醇 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以65%的产率得到1-(4,4-dimethoxybutyl)-4,4-dimethylcyclopent-2-en-1-ol
  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