2-butyl-3-fluoro-5-methylene-2-cyclopenten-1-one | 164406-17-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-butyl-3-fluoro-5-methylene-2-cyclopenten-1-one
• 英文别名: 2-butyl-3-fluoro-5-methylidenecyclopent-2-en-1-one
• CAS: 164406-17-1
• 化学式: C₁₀H₁₃FO
• 分子量: 168.211
• InChiKey: PMRKVRFLSRLHIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-butyl-3-fluoro-5-methylene-2-cyclopenten-1-one 、 环己醇 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.13h， 以79%的产率得到2-butyl-3-cyclohexyloxy-5-methylene-2-cyclopenten-1-one
  参考文献：
  名称：

  Regioselective Nucleophilic Additions to Cross-Conjugated Dienone System Bearing β-Fluorine:  A Versatile Approach to Highly Substituted 2-Cyclopentenones

  摘要：

  [GRAPHICS]3-Fluoro-5-methylene-2-cyclopentenone is treated with appropriate nucleophiles and Lewis acids to undergo regioselective 1,2-addition, exocyclic 1,4-addition, and endocyclic 1,4 addition, leading to 3-substituted 4-methylene-2-cyclopentenones, 5-substituted 3-fluoro-2-cyclopentenones, and 3-substituted 5-methylene-2-cyclopentenones in good yields, respectively.

  DOI：

  10.1021/ol0161458
• 作为产物：
  描述：

  2-butyl-1,1-difluoro-4-methyl-1,4-pentadien-3-one 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.13h， 以73%的产率得到2-butyl-3-fluoro-5-methylene-2-cyclopenten-1-one
  参考文献：
  名称：

  Regioselective Nucleophilic Additions to Cross-Conjugated Dienone System Bearing β-Fluorine:  A Versatile Approach to Highly Substituted 2-Cyclopentenones

  摘要：

  [GRAPHICS]3-Fluoro-5-methylene-2-cyclopentenone is treated with appropriate nucleophiles and Lewis acids to undergo regioselective 1,2-addition, exocyclic 1,4-addition, and endocyclic 1,4 addition, leading to 3-substituted 4-methylene-2-cyclopentenones, 5-substituted 3-fluoro-2-cyclopentenones, and 3-substituted 5-methylene-2-cyclopentenones in good yields, respectively.

  DOI：

  10.1021/ol0161458

文献信息

• Fluorine-Directed Nazarov Cyclizations: A Controlled Synthesis of Cross-Conjugated 2-Cyclopenten-1-ones
  作者：Junji Ichikawa、Shinji Miyazaki、Masaki Fujiwara、Toru Minami

  DOI：10.1021/jo00113a005

  日期：1995.4
• Regioselective Nucleophilic Additions to Cross-Conjugated Dienone System Bearing β-Fluorine:  A Versatile Approach to Highly Substituted 2-Cyclopentenones
  作者：Junji Ichikawa、Masaki Fujiwara、Shinji Miyazaki、Masahiro Ikemoto、Tatsuo Okauchi、Toru Minami

  DOI：10.1021/ol0161458

  日期：2001.7.1

  [GRAPHICS]3-Fluoro-5-methylene-2-cyclopentenone is treated with appropriate nucleophiles and Lewis acids to undergo regioselective 1,2-addition, exocyclic 1,4-addition, and endocyclic 1,4 addition, leading to 3-substituted 4-methylene-2-cyclopentenones, 5-substituted 3-fluoro-2-cyclopentenones, and 3-substituted 5-methylene-2-cyclopentenones in good yields, respectively.