2-(2-butynyl)-2-ethylmalonic acid monomethyl ester | 1374404-29-1

• 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 monomethyl ester
• 英文别名: 2-Ethyl-2-methoxycarbonylhex-4-ynoic acid
• CAS: 1374404-29-1
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: HEVFIHMUSGYGRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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-(2-butynyl)-2-ethylmalonic acid monomethyl ester 在 C₁₂H₁₅AuCl₃N₃O₃S 、 水 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以94%的产率得到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 在 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(2-butynyl)-2-ethylmalonic 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

文献信息

• Water-Soluble Gold(I) and Gold(III) Complexes with Sulfonated <i>N</i>-Heterocyclic Carbene Ligands: Synthesis, Characterization, and Application in the Catalytic Cycloisomerization of γ-Alkynoic Acids into Enol-Lactones
  作者：Eder Tomás-Mendivil、Patrick Y. Toullec、Javier Borge、Salvador Conejero、Véronique Michelet、Victorio Cadierno

  DOI：10.1021/cs4009144

  日期：2013.12.6

  2-pyridyl, 2-picolyl, and 2-pyridylethyl substituents have been synthesized and employed as precursors for the preparation of novel water-soluble Au(I)- and Au(III)-NHC complexes of general composition [AuCl(NHC)] and [AuCl3(NHC)] (NHC = N-heterocyclic carbene), respectively. These complexes proved to be active, selective, and recyclable catalysts for the intramolecular cyclization of γ-alkynoic acids under

  合成了带有3-磺酰基丙基，2-吡啶基，2-吡啶基和2-吡啶基乙基取代基的两性离子咪唑鎓盐，并将其用作制备新型水溶性Au（I）-和Au（III）-NHC配合物的前体组成[AuCl（NHC）]和[AuCl 3（NHC）]（NHC = N-杂环卡宾）。这些络合物被证明是在双相甲苯/水条件下用于γ-链烷酸分子内环化的活性，选择性和可回收催化剂，从而在温和条件下（rt）以高收率得到所需的烯醇内酯。值得注意的是，尽管众所周知金络合物具有促进C≡C键水合的能力，但即使在1,6-二炔的环异构化反应过程中也未观察到竞争水合过程。