3-(2-烯丙基苯基)-3-氧代丙酸甲酯 | 1325230-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(2-烯丙基苯基)-3-氧代丙酸甲酯
• 英文名称: methyl 3-(2-allylphenyl)-3-oxopropanoate
• 英文别名: Methyl 3-oxo-3-(2-prop-2-enylphenyl)propanoate
• CAS: 1325230-66-7
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: SCOUFALMFKODSN-UHFFFAOYSA-N

物化性质

• 沸点：
  310.4±30.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-烯丙基苯基)-3-氧代丙酸甲酯 在 palladium(II) trifluoroacetate 、 copper diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以64%的产率得到1-羟基-3-甲基萘-2-羧酸甲酯
  参考文献：
  名称：

  Pd-Catalyzed Sequential C–C Bond Formation and Cleavage: Evidence for an Unexpected Generation of Arylpalladium(II) Species

  摘要：

  A Pd(II)-catalyzed reaction engaging alkenyl beta-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium-(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven beta-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.

  DOI：

  10.1021/ja304616q
• 作为产物：
  描述：

  在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以59%的产率得到3-(2-烯丙基苯基)-3-氧代丙酸甲酯
  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