methyl 3-(but-2-ynyl)-6-methyl-2-oxo-3,4-dihydro-2H-pyran-3-carboxylate | 1231753-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 3-(but-2-ynyl)-6-methyl-2-oxo-3,4-dihydro-2H-pyran-3-carboxylate
• 英文别名: 3-(2-butynyl)-6-methyl-2-oxo-3,4-dihydro-2H-pyran-3-carboxylic acid methyl ester；methyl 3-but-2-ynyl-6-methyl-2-oxo-4H-pyran-3-carboxylate
• CAS: 1231753-33-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: PZQCJKQVLIIIGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(but-2-ynyl)-2-(methoxycarbonyl)hex-4-ynoic acid 在 silica supported carbene gold(I)complex 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 生成 methyl 3-(but-2-ynyl)-6-methyl-2-oxo-3,4-dihydro-2H-pyran-3-carboxylate 、 3-(2-butynyl)-5-ethylidene-2-oxotetrahydrofuran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Sol-Gel固定化的N-杂环碳金复合物作为可循环利用的催化剂，用于烯丙基酯的重排和γ-炔酸的环异构化

  摘要：

  描述了双硅烷化（NHC）AuCl（NHC = N-杂环卡宾）配合物的合成，以及在氟化物催化下与原硅酸四乙酯共凝胶化通过溶胶-凝胶法形成的杂化二氧化硅材料。通过使用29 Si固态NMR光谱N 2对该材料进行了表征吸附测量，电子显微镜和元素分析。在微波条件下，它与银盐一起用于烯丙基酯与银盐的重排中作为可重复使用的催化剂进行了测试，它的性能比均相类似物好得多。该催化剂在室温下在两种反应介质（甲苯/水两相系统和深共熔溶剂）中，将γ-链烷酸环化为五元烯醇-内酯时具有活性且可循环利用。

  DOI：

  10.1002/cctc.201600632

文献信息

• Gold-Catalyzed Tandem Cyclizations of 1,6-Diynes Triggered by Internal N- and O-Nucleophiles
  作者：Christian A. Sperger、Anne Fiksdahl

  DOI：10.1021/jo100712d

  日期：2010.7.2

  Investigations on gold-catalyzed tandem cyclization reactions of 1,6-diynes, tethered to nucleophilic functionalities such as amine, carboxylic acid, amide, and sulfonamide, are reported. The ability of such substrates to undergo tandem cyclization, triggered by internal nucleophiles, has been examined. Depending on the substrate, the catalytic system, and reaction conditions, different regioisomers of monocyclic and bridged bicyclic products were obtained.
• Cycloisomerization versus Hydration Reactions in Aqueous Media: A Au(III)-NHC Catalyst That Makes the Difference
  作者：Eder Tomás-Mendivil、Patrick Y. Toullec、Josefina Díez、Salvador Conejero、Véronique Michelet、Victorio Cadierno

  DOI：10.1021/ol300811e

  日期：2012.5.18

  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.
• Sol-Gel Immobilized N-Heterocyclic Carbene Gold Complex as a Recyclable Catalyst for the Rearrangement of Allylic Esters and the Cycloisomerization of γ-Alkynoic Acids
  作者：Meritxell Ferré、Xavier Cattoën、Michel Wong Chi Man、Roser Pleixats

  DOI：10.1002/cctc.201600632

  日期：2016.9.7

  The synthesis of a bis‐silylated (NHC)AuCl (NHC=N‐heterocyclic carbene) complex and the formation of a hybrid silica material by the sol–gel process by cogelification with tetraethylorthosilicate under fluoride catalysis are described. This material was characterized by using 29Si solid‐state NMR spectroscopy, N2 sorption measurements, electron microscopy, and elemental analysis. It was tested as a

  描述了双硅烷化（NHC）AuCl（NHC = N-杂环卡宾）配合物的合成，以及在氟化物催化下与原硅酸四乙酯共凝胶化通过溶胶-凝胶法形成的杂化二氧化硅材料。通过使用29 Si固态NMR光谱N 2对该材料进行了表征吸附测量，电子显微镜和元素分析。在微波条件下，它与银盐一起用于烯丙基酯与银盐的重排中作为可重复使用的催化剂进行了测试，它的性能比均相类似物好得多。该催化剂在室温下在两种反应介质（甲苯/水两相系统和深共熔溶剂）中，将γ-链烷酸环化为五元烯醇-内酯时具有活性且可循环利用。