3-[(2-E)-6-(5,5-dimethyl-1-oxocyclopent-2-en-3-yl)-1-oxohex-2-enyl]-2-oxazolidinone | 244308-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-[(2-E)-6-(5,5-dimethyl-1-oxocyclopent-2-en-3-yl)-1-oxohex-2-enyl]-2-oxazolidinone
• 英文别名: 3-[(E)-6-(4,4-dimethyl-3-oxocyclopenten-1-yl)hex-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 244308-20-1
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: CQUQXEOWMQVKFJ-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(2-E)-6-(5,5-dimethyl-1-oxocyclopent-2-en-3-yl)-1-oxohex-2-enyl]-2-oxazolidinone 在 bis(1,5-cyclooctadiene)nickel (0) 、 diethylzinc 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到(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 在 4-二甲氨基吡啶 、 florisil 、 叔丁基锂 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 丙酮 、 正戊烷 为溶剂， 反应 7.33h， 生成 3-[(2-E)-6-(5,5-dimethyl-1-oxocyclopent-2-en-3-yl)-1-oxohex-2-enyl]-2-oxazolidinone
  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

• 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.