2-(2-butynyl)-2-ethylmalonic acid dimethyl ester | 1374404-21-3

• 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-(2-butynyl)-2-ethylmalonic acid dimethyl ester
• 英文别名: Dimethyl 2-but-2-ynyl-2-ethylpropanedioate；dimethyl 2-but-2-ynyl-2-ethylpropanedioate
• CAS: 1374404-21-3
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: LXNCKNLFZWYOJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-butynyl)-2-ethylmalonic acid dimethyl ester 在 C₁₂H₁₅AuCl₃N₃O₃S 、 水 、 potassium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 3-ethyl-5-ethylidene-2-oxotetrahydrofuran-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：

  乙基丙二酸二甲酯 、 1-溴-2-丁炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到2-(2-butynyl)-2-ethylmalonic acid dimethyl 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