2-(3-phenyl-2-propynyl)-2-(2-propynyl)malonic acid monomethyl ester | 1374404-43-9

• 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: 2-(3-phenyl-2-propynyl)-2-(2-propynyl)malonic acid monomethyl ester
• 英文别名: 2-Methoxycarbonyl-5-phenyl-2-prop-2-ynylpent-4-ynoic acid
• CAS: 1374404-43-9
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: WSMMPEWYAOVNNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-phenyl-2-propynyl)-2-(2-propynyl)malonic acid monomethyl ester 在 C₁₂H₁₅AuCl₃N₃O₃S 、 水 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以86%的产率得到5-methylene-2-oxo-3-(3-phenyl-2-propynyl)tetrahydrofuran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Cycloisomerization versus Hydration Reactions in Aqueous Media: A Au(III)-NHC Catalyst That Makes the Difference

  摘要：

  A novel water-soluble Au(III)-NHC complex has been synthesized and successfully applied in the intramolecular cyclization of gamma-alkynoic acids into enol-lactones under biphasic toluene/water conditions, thus representing a rare example of an active and selective catalyst for this transformation In aqueous media. Remarkably, competing alkyne hydration processes were not observed, even during the desymmetrization reaction of challenging 1,6-diyne substrates. In addition, after phase separation, the water-soluble Au(III) catalyst could be recycled 10 times without loss of activity or selectivity.

  DOI：

  10.1021/ol300811e
• 作为产物：
  描述：

  2-(3-phenyl-prop-2-ynyl)-2-prop-2-ynyl-malonic acid dimethyl ester 在 potassium hydroxide 、 水 、 碳酸氢钠 、 盐酸 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 以77%的产率得到2-(3-phenyl-2-propynyl)-2-(2-propynyl)malonic acid monomethyl ester
  参考文献：
  名称：

  Cycloisomerization versus Hydration Reactions in Aqueous Media: A Au(III)-NHC Catalyst That Makes the Difference

  摘要：

  A novel water-soluble Au(III)-NHC complex has been synthesized and successfully applied in the intramolecular cyclization of gamma-alkynoic acids into enol-lactones under biphasic toluene/water conditions, thus representing a rare example of an active and selective catalyst for this transformation In aqueous media. Remarkably, competing alkyne hydration processes were not observed, even during the desymmetrization reaction of challenging 1,6-diyne substrates. In addition, after phase separation, the water-soluble Au(III) catalyst could be recycled 10 times without loss of activity or selectivity.

  DOI：

  10.1021/ol300811e