methyl 2-benzoyl-3-methylenetetrahydrofuran-2-carboxylate | 1536143-73-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-benzoyl-3-methylenetetrahydrofuran-2-carboxylate
• 英文别名: Methyl 2-benzoyl-3-methylideneoxolane-2-carboxylate；methyl 2-benzoyl-3-methylideneoxolane-2-carboxylate
• CAS: 1536143-73-3
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: IAFDTGARBHSEGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-diazo-3-oxo-3-phenyl-propionic acid methyl ester 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 palladium diacetate 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 methyl 2-benzoyl-3-methylenetetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Formal [4 + 1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans

  摘要：

  A novel formal [4 + 1]-cycloaddition of readily available homopropargyl alcohols with diazo dicarbonyl compounds is described, which involves tandem O-H insertion/Conia-ene cyclization under cooperative Rh(II)/Zn(II) catalysis. This reaction provides easy access to various substituted tetrahydrofurans and exhibits complete E-selectivity in the case of nonterminal alkynes.

  DOI：

  10.1021/ol403746r

文献信息

• Synergistic Diazo-OH Insertion/Conia-Ene Cascade Catalysis for the Stereoselective Synthesis of<i>γ</i>-Butyrolactones and Tetrahydrofurans
  作者：Arianne C. Hunter、Steven C. Schlitzer、Indrajeet Sharma

  DOI：10.1002/chem.201603934

  日期：2016.11.2

  A novel and highly efficient diazo‐OH insertion/Conia‐ene cascade reaction of readily available homopropargylic acids and alcohols with diazo carbonyl compounds is described. The cascade reaction involves a synergistic Rh/Ag/Au catalyst cocktail and proceeds instantly with a variety of substituted diazo compounds and acids/alcohols to provide functionalized γ‐butyrolactones and tetrahydrofurans with

  描述了一种新颖，高效的重氮-OH插入/苯并-烯级联反应，该反应可容易获得的均丙酸和醇与重氮羰基化合物。级联反应涉及协同的Rh / Ag / Au催化剂混合物，并立即与多种取代的重氮化合物和酸/醇进行反应，以提供具有完全区域和立体选择性的官能化γ-丁内酯和四氢呋喃。空前的速率增强，完全的立体选择性以及新的Coniaene环化的实现表明在协同（Rh / Ag / Au）催化条件下，一致的[4 + 1]-环加成反应途径。
• Formal [4 + 1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans
  作者：Fumiya Urabe、Shohei Miyamoto、Keisuke Takahashi、Jun Ishihara、Susumi Hatakeyama

  DOI：10.1021/ol403746r

  日期：2014.2.7

  A novel formal [4 + 1]-cycloaddition of readily available homopropargyl alcohols with diazo dicarbonyl compounds is described, which involves tandem O-H insertion/Conia-ene cyclization under cooperative Rh(II)/Zn(II) catalysis. This reaction provides easy access to various substituted tetrahydrofurans and exhibits complete E-selectivity in the case of nonterminal alkynes.