(Z)-4-isopropyl-5-phenyl-methylidene-γ-butyrolactone | 1188310-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-4-isopropyl-5-phenyl-methylidene-γ-butyrolactone
• 英文别名: (Z)-4-isopropyl-5-phenylmethylidene-γ-butyrolactone；(5Z)-5-benzylidene-4-propan-2-yloxolan-2-one
• CAS: 1188310-08-8
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: YMSRHGATVLMLAO-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-isopropyl-5-phenylpent-4-ynoic acid 在 iron(III) chloride 、 copper diacetate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以68%的产率得到(Z)-4-isopropyl-5-phenyl-methylidene-γ-butyrolactone
  参考文献：
  名称：

  铜/铁共催化的高选择性串联反应：Z -γ-亚烷基内酯的有效方法

  摘要：

  Abstractmagnified imageInexpensive copper/iron‐cocatalyzed, efficient, highly regioselective and stereoselective one‐pot tandem conjugate addition–cyclization–hydrolysis–decarboxylation reactions have been developed, which provide efficient tandem reactions for CC and CO bond formation, and the novel synthetic methods of γ‐alkylidenebutyrolactones.

  DOI：

  10.1002/adsc.200800695

文献信息

• AgNO3 catalyzed cyclization of propargyl-Meldrum’s acids in aqueous solvent: highly selective synthesis of Z-γ-alkylidene lactones
  作者：Wei Jia、Si Li、Miao Yu、Wei Chen、Ning Jiao

  DOI：10.1016/j.tetlet.2009.07.050

  日期：2009.9

  γ-Alkylidene lactones have attracted considerable attention due to their diverse biological activities and ubiquitous structural units in natural products. Herein, an efficient AgNO3 catalyzed highly regio- and stereo-selective cyclization of propargyl-Meldrum’s acids in aqueous solvent was developed, which provides a practical synthetic strategy for the synthesis of substituted Z-γ-alkylidene butyrolactones

  γ-亚烷基内酯由于其多样的生物活性和天然产物中普遍存在的结构单元而引起了相当大的关注。在此，开发了一种有效的AgNO 3在水性溶剂中催化炔丙基-麦德鲁姆酸的高度区域和立体选择性环化的方法，为在中性反应条件下合成取代的Z -γ-亚烷基丁内酯提供了实用的合成策略。
• Copper/Iron-Cocatalyzed Highly Selective Tandem Reactions: Efficient Approaches to<i>Z-</i>γ-Alkylidene Lactones
  作者：Si Li、Wei Jia、Ning Jiao

  DOI：10.1002/adsc.200800695

  日期：2009.3

  Abstractmagnified imageInexpensive copper/iron‐cocatalyzed, efficient, highly regioselective and stereoselective one‐pot tandem conjugate addition–cyclization–hydrolysis–decarboxylation reactions have been developed, which provide efficient tandem reactions for CC and CO bond formation, and the novel synthetic methods of γ‐alkylidenebutyrolactones.