(Z)-methyl 2-(3,3-dimethylisochroman-1-ylidene)acetate | 1325230-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (Z)-methyl 2-(3,3-dimethylisochroman-1-ylidene)acetate
• 英文别名: methyl (2Z)-2-(3,3-dimethyl-4H-isochromen-1-ylidene)acetate
• CAS: 1325230-37-2
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: DHRSOCRWHFPHJC-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 3-(2-(2-methylallyl)phenyl)-3-oxopropanoate 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 13.0h， 以49%的产率得到1,3-二甲基萘
  参考文献：
  名称：

  Cyclization Reaction for the Synthesis of Polysubstituted Naphthalenes in the Presence of Au(I) Precatalysts

  摘要：

  Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the pi-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.

  DOI：

  10.1021/jo201339z

文献信息

• Cyclization Reaction for the Synthesis of Polysubstituted Naphthalenes in the Presence of Au(I) Precatalysts
  作者：Arun R. Jagdale、Jong Hyub Park、So Won Youn

  DOI：10.1021/jo201339z

  日期：2011.9.2

  Au(I)-catalyzed cyclization of alkenyl carbonyl compounds leading to a variety of substituted naphthalenes has been developed. This process exploits a dual function of the Au(I) catalyst: (1) the oxophilic nature of the Au(I) catalyst, counterintuitive to the pi-acidic reactivities generally associated with Au catalysts, and (2) olefin isomerization supported by the outcome of isotope scrambling experiments. It cannot be completely excluded that TfOH is a true operative catalyst in this protocol. In view of the practicality, the unnecessity of isomerically pure starting material in this reaction is particularly attractive and valuable.