ethyl 5-tert-butylpenta-2,3-dienoate | 1422199-49-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 5-tert-butylpenta-2,3-dienoate
• CAS: 1422199-49-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: XFCOFIUQSFHCEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 5-tert-butylpenta-2,3-dienoate 在 palladium 10% on activated carbon 、 氢气 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 ethyl 2'-oxo-6'-chloro-2-(3-chloro-2-fluorophenyl)-5-neopentylspiro[cyclopentane-1,3'-indoline]-3-carboxylate
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications

  摘要：

  The phosphine-promoted [3 + 2] cyclizations between gamma-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh3 operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.

  DOI：

  10.1021/jo302460d
• 作为产物：
  描述：

  2,2-二甲基戊酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 ethyl 5-tert-butylpenta-2,3-dienoate
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications

  摘要：

  The phosphine-promoted [3 + 2] cyclizations between gamma-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh3 operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.

  DOI：

  10.1021/jo302460d

文献信息

• Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications
  作者：Catherine Gomez、Maxime Gicquel、Jean-Christophe Carry、Laurent Schio、Pascal Retailleau、Arnaud Voituriez、Angela Marinetti

  DOI：10.1021/jo302460d

  日期：2013.2.15

  The phosphine-promoted [3 + 2] cyclizations between gamma-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh3 operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.