5,5-Dicyclohexyl-4,5-dihydro-2(3H)-furanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5,5-Dicyclohexyl-4,5-dihydro-2(3H)-furanone
• 英文别名: 5,5-dicyclohexyldihydrofuran-2(3H)-one；5,5-Dicyclohexyloxolan-2-one
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: GFGRJKHEWSUOGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(Benzotriazol-1-yl)-1,1-dicyclohexyl-4-ethoxybut-3-en-1-ol 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5,5-Dicyclohexyl-4,5-dihydro-2(3H)-furanone
  参考文献：
  名称：

  A Novel Heterocycle-Stabilized Allylic Anion Route to Cyclopropanes, 1-Ethoxy-1-vinylethylene Oxides, 1-Hydroxyalkyl 2-Methoxyethyl Ketones, 1-Hydroxyalkyl Vinyl Ketones, .beta.-Ethoxy-.beta.-vinylalkyl Alcohols, .gamma.-Lactones, and .beta.,.gamma.-Unsaturated Carboxylic Acids

  摘要：

  Treatment of N-(alpha-ethoxyallyl)benzotriazole (8) with butyllithium followed by alpha,beta-unsaturated esters at -78 degrees C formed the 1,1-adducts 11 which underwent internal displacement of the benzotriazolyl group at 20 degrees C to give cyclopropanecarboxylic esters 14 and 15. In the presence of ZnBr2, addition of anion 13 to cyclic and methyl ketones gave 1-ethoxy-1-vinylethylene oxides 25 in good yields. Epoxides 25 were subsequently converted to 1-hydroxyalkyl 2-methoxyethyl ketones 24, 1-hydroxyalkyl vinyl ketones 26, and beta-ethoxy-beta-vinylalkyl alcohols 27. Treatment of anion 13 with aromatic ketones or sterically hindered aliphatic ketones produced gamma-alkylated adducts 31 which were hydrolyzed to beta,gamma-unsaturated carboxylic acids 32 (R(1), R(2) = aromatic) or gamma-lactones 33 (R(1), R(2) = aliphatic).

  DOI：

  10.1021/jo00128a036

文献信息

• Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool To Study Photoredox Reactions
  作者：Ierasia Triandafillidi、Maroula G. Kokotou、Christoforos G. Kokotos

  DOI：10.1021/acs.orglett.7b03256

  日期：2018.1.5

  A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)3Cl2 as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry.

  已经开发了用于合成γ-内酯的温和光催化歧管。利用Ru（bpy）3 Cl 2作为光催化剂，已经引入了廉价且可重现的γ-内酯合成方案。机理研究表明，通过高分辨率质谱已成功监测了光催化反应和自由基中间体。
• A Novel Heterocycle-Stabilized Allylic Anion Route to Cyclopropanes, 1-Ethoxy-1-vinylethylene Oxides, 1-Hydroxyalkyl 2-Methoxyethyl Ketones, 1-Hydroxyalkyl Vinyl Ketones, .beta.-Ethoxy-.beta.-vinylalkyl Alcohols, .gamma.-Lactones, and .beta.,.gamma.-Unsaturated Carboxylic Acids
  作者：Alan R. Katritzky、Jinlong Jiang

  DOI：10.1021/jo00128a036

  日期：1995.11

  Treatment of N-(alpha-ethoxyallyl)benzotriazole (8) with butyllithium followed by alpha,beta-unsaturated esters at -78 degrees C formed the 1,1-adducts 11 which underwent internal displacement of the benzotriazolyl group at 20 degrees C to give cyclopropanecarboxylic esters 14 and 15. In the presence of ZnBr2, addition of anion 13 to cyclic and methyl ketones gave 1-ethoxy-1-vinylethylene oxides 25 in good yields. Epoxides 25 were subsequently converted to 1-hydroxyalkyl 2-methoxyethyl ketones 24, 1-hydroxyalkyl vinyl ketones 26, and beta-ethoxy-beta-vinylalkyl alcohols 27. Treatment of anion 13 with aromatic ketones or sterically hindered aliphatic ketones produced gamma-alkylated adducts 31 which were hydrolyzed to beta,gamma-unsaturated carboxylic acids 32 (R(1), R(2) = aromatic) or gamma-lactones 33 (R(1), R(2) = aliphatic).