3-(2-chloroprop-2-en-1-yl)-5,5-dimethyltetrahydrofuran-2-one | 1174396-63-4

• 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-(2-chloroprop-2-en-1-yl)-5,5-dimethyltetrahydrofuran-2-one
• 英文别名: 3-(2-Chloroprop-2-en-1-yl)-5,5-dimethyltetra-hydrofuran-2-one；3-(2-chloroprop-2-enyl)-5,5-dimethyloxolan-2-one
• CAS: 1174396-63-4
• 化学式: C₉H₁₃ClO₂
• 分子量: 188.654
• InChiKey: KGPDCYCFHMMJNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-(2-chloroprop-2-en-1-yl)-5,5-dimethyltetrahydrofuran-2-one 在 硫酸 、 水 作用下， 生成 5,5-dimethyl-3-(2-oxopropyl)tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis of 5-substituted 3-(2-oxopropyl)tetrahydrofuran-2-ones and heterocyclic compounds on their base

  摘要：

  Alkylation of ethyl 2-oxotetrahydrofuran-3-carboxylates with 2,3-dichloroprop-1-ene and 3-bromoprop-1-yne gave new 3,5,5-tri- and 3,3,5,5-tetrasubstituted tetrahydrofuran-2-ones which were converted into the corresponding 3-(2-oxopropyl)tetrahydrofuran-2-ones. Reactions of the latter with semicarabazide, thiosemicarbazide, and phenylhydrazine were studied with a view to obtain new heterocyclic lactones.

  DOI：

  10.1134/s1070428008120130
• 作为产物：
  描述：

  ethyl 3-(2-chloroprop-2-en-1-yl)-5-methyl-2-oxotetrahydrofuran-3-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.5h， 以78%的产率得到3-(2-chloroprop-2-en-1-yl)-5,5-dimethyltetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis of 5-substituted 3-(2-oxopropyl)tetrahydrofuran-2-ones and heterocyclic compounds on their base

  摘要：

  Alkylation of ethyl 2-oxotetrahydrofuran-3-carboxylates with 2,3-dichloroprop-1-ene and 3-bromoprop-1-yne gave new 3,5,5-tri- and 3,3,5,5-tetrasubstituted tetrahydrofuran-2-ones which were converted into the corresponding 3-(2-oxopropyl)tetrahydrofuran-2-ones. Reactions of the latter with semicarabazide, thiosemicarbazide, and phenylhydrazine were studied with a view to obtain new heterocyclic lactones.

  DOI：

  10.1134/s1070428008120130

文献信息

• Application of Suzuki-Miyaura Reaction in the Chemistry of Oxolan-2-ones
  作者：T. V. Ghochikyan、A. S. Vardanyan、M. A. Samvelyan、A. S. Galstyan、P. Langer

  DOI：10.1134/s1070428019020258

  日期：2019.2

  The reactions of 2-(2-chloroprop-2-en-1-yl)-5,5-dimethyloxolan-2-one with arylboronic acids in the presence of Pd(PPh3)(4) and K2CO3 was used to synthesize novel oxolan-2-one derivatives3-[(2-aryl)prop-2-en-1-yl]-5,5-dimethyloxolan-2-ones. The reaction conditions were optimized for the highest yields of the target products.