3-benzyl-5,5-dimethyltetrahydrofuran-2-one | 51849-73-1

• 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: 3-benzyl-5,5-dimethyltetrahydrofuran-2-one
• 英文别名: 3-benzyl-5,5-dimethyl-dihydro-furan-2-one；3-Benzyl-5,5-dimethyloxolan-2-one
• CAS: 51849-73-1
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: PYHHNUZYJVNRMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-5,5-dimethyltetrahydrofuran-2-one 在 肼 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 以70%的产率得到2-benzyl-4-hydroxy-4-methylpentanehydrazide
  参考文献：
  名称：

  New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates

  摘要：

  Alkylation of 5-substituted ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylates with alkyl halides in the presence of sodium ethoxide gave the corresponding 3-alkyl derivatives which were converted into 3,5-substituted 5-methyl-N-(4-nitrophenyl)-2-oxotetrahydrofuran-3-carboxamides and 5-methyltetrahydrofuran-2-ones. Reactions of the latter with hydrazine hydrate led to the formation of 4-hydroxypentanoic acid hydrazides which were treated with isothiocyanates to obtain the corresponding thiosemicarbazides whose intramolecular cyclization in the presence of aqueous alkali gave previously unknown 1,2,4-triazole-3-thiol derivatives.

  DOI：

  10.1134/s1070428008060122
• 作为产物：
  描述：

  2-Benzyl-4-oxopentanoic acid 在 氢气 作用下， 生成 3-benzyl-5,5-dimethyltetrahydrofuran-2-one
  参考文献：
  名称：

  Cycloshydratation de dios in presence D'HMPT

  摘要：

  DOI：

  10.1016/s0040-4039(00)98535-6

文献信息

• Unusual iodine catalyzed lactonization of γ-methyl-γ,δ-pentenoic acids: A facile synthesis of γ,γ-dimethyl-γ-butyrolactones
  作者：Kyoung Mahn Kim、Eung K. Ryu

  DOI：10.1016/0040-4039(96)00026-3

  日期：1996.2

  γ,γ-Dimethyl-γ-butyrolactones were exclusively obtained from γ-methyl-γ,δ-pentenoic acids with a catalytic amount of iodine in good yields in methylene chloride.

  γ，γ-二甲基-γ-丁内酯仅从γ-甲基-γ，δ-戊烯酸中以催化量的碘在二氯甲烷中以高收率获得。
• Combined dealkoxycarbonylation and lactonisation of unsaturated malonates in ionic liquids
  作者：Magalie F. Oswald、Andrew F. Parsons、Wei Yang、Martin Bowden

  DOI：10.1016/j.tetlet.2005.09.143

  日期：2005.11

  Heating unsaturated malonates with LiCl and water in [bmim][Br] or [bmim][BF4]/[bmim][Br] produces unsaturated esters or lactones, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
• New syntheses on the basis of ethyl 2-oxotetrahydrofuran-3-carboxylates
  作者：T. V. Kochikyan、E. V. Arutyunyan、V. S. Arutyunyan、A. A. Avetisyan

  DOI：10.1134/s1070428008060122

  日期：2008.6

  Alkylation of 5-substituted ethyl 5-methyl-2-oxotetrahydrofuran-3-carboxylates with alkyl halides in the presence of sodium ethoxide gave the corresponding 3-alkyl derivatives which were converted into 3,5-substituted 5-methyl-N-(4-nitrophenyl)-2-oxotetrahydrofuran-3-carboxamides and 5-methyltetrahydrofuran-2-ones. Reactions of the latter with hydrazine hydrate led to the formation of 4-hydroxypentanoic acid hydrazides which were treated with isothiocyanates to obtain the corresponding thiosemicarbazides whose intramolecular cyclization in the presence of aqueous alkali gave previously unknown 1,2,4-triazole-3-thiol derivatives.
• Cycloshydratation de dios in presence D'HMPT
  作者：J Diab、M Abou-Assali、C Gervais、D Anker

  DOI：10.1016/s0040-4039(00)98535-6

  日期：——