1-((Z)-2-Fluoro-3-piperidin-1-yl-allylidene)-piperidinium; iodide | 139680-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-((Z)-2-Fluoro-3-piperidin-1-yl-allylidene)-piperidinium; iodide
• 英文别名: 1-(2-fluoro-3-piperidin-1-ium-1-ylideneprop-1-enyl)piperidine;iodide
• CAS: 139680-76-5
• 化学式: C₁₃H₂₂FN₂*I
• 分子量: 352.234
• InChiKey: HQLKNGFRRARVRE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((Z)-2-Fluoro-3-piperidin-1-yl-allylidene)-piperidinium; iodide 、 3-戊酮 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以52%的产率得到(4E,6Z)-6-fluoro-4-methyl-7-piperidin-1-ylhepta-4,6-dien-3-one
  参考文献：
  名称：

  Reactions of β-fluorovinamidinium salt with activated methylene compounds

  摘要：

  beta-Fluoro vinamidinium salt (1) reacted with 1.1 equiv. of methylene compounds activated with carbonyl or cyano groups in the presence of lithium diisopropylamide or sodium hydride and triethylamine in tetrahydrofuran at room temperature to give monofluorinated multifunctional dienaminones (3) and dienaminonitriles (5) in moderate to good yields. The reactions of 1 with 2.2 equiv. of enolates derived from beta-keto esters at 80 degrees C gave the cyclization products, fluorinated isophthalates (6) in good yields, while a similar reaction with 2.2 equiv. of cyanoacetate and malononitrile produced the non-cyclic 1,3-dienecarbonitriles (7) in excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00794-1
• 作为产物：
  描述：

  哌啶 、 (2,3,3-三氟-1-丙烯基)三甲基碘化铵 以 二甲基亚砜 为溶剂， 反应 1.0h， 以58%的产率得到1-((Z)-2-Fluoro-3-piperidin-1-yl-allylidene)-piperidinium; iodide
  参考文献：
  名称：

  制备β-氟乙烯基ami盐的极其简单的方法：（聚氟-1-丙烯基）三甲基碘化碘与伯胺或仲胺的新型反应

  摘要：

  （2,3,3-三氟-1-丙烯基）三甲基碘化碘易于在环境温度或70°C下通过各种仲胺或几种伯胺的作用进行脱甲基化烯丙基取代，然后进行NN交换反应，得到相应的β -氟化的乙烯基ami胺盐，收率高。

  DOI：

  10.1016/s0040-4039(00)74130-x

文献信息

• Extremely simple route to β-fluoro vinamidinium salts: A novel reaction of (polyfluoro-1-propenyl)trimethylammonium iodides with primary or secondary amines
  作者：Hiroki Yamanaka、Seiji Yamashita、Takashi Ishihara

  DOI：10.1016/s0040-4039(00)74130-x

  日期：1992.1

  3-Trifluoro-1-propenyl)trimethylammonium iodides readily underwent demethylation-allylic substitution followed by N-N exchange reaction at ambient temperature or at 70 °C by the action of various secondary amines or several primary amines to give the corresponding β-fluorinated vinamidinium salts in good yields.

  （2,3,3-三氟-1-丙烯基）三甲基碘化碘易于在环境温度或70°C下通过各种仲胺或几种伯胺的作用进行脱甲基化烯丙基取代，然后进行NN交换反应，得到相应的β -氟化的乙烯基ami胺盐，收率高。
• Reactions of β-fluorovinamidinium salt with activated methylene compounds
  作者：Hiroki Yamanaka、Kazuma Hisaki、Koichiro Kase、Takashi Ishihara、John T. Gupton

  DOI：10.1016/s0040-4039(98)00794-1

  日期：1998.6

  beta-Fluoro vinamidinium salt (1) reacted with 1.1 equiv. of methylene compounds activated with carbonyl or cyano groups in the presence of lithium diisopropylamide or sodium hydride and triethylamine in tetrahydrofuran at room temperature to give monofluorinated multifunctional dienaminones (3) and dienaminonitriles (5) in moderate to good yields. The reactions of 1 with 2.2 equiv. of enolates derived from beta-keto esters at 80 degrees C gave the cyclization products, fluorinated isophthalates (6) in good yields, while a similar reaction with 2.2 equiv. of cyanoacetate and malononitrile produced the non-cyclic 1,3-dienecarbonitriles (7) in excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.