N-(2-fluorocyclohexyl)benzamide | 79102-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-fluorocyclohexyl)benzamide
• 英文别名: trans-N-benzoyl-2-fluorocyclohexylamine；N-(trans-2-fuorocyclohexyl)benzamide；N-[(1S,2S)-2-fluorocyclohexyl]benzamide
• CAS: 79102-43-5
• 化学式: C₁₃H₁₆FNO
• 分子量: 221.275
• InChiKey: CBNAHXNSBDXSRK-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-fluorocyclohexyl)benzamide 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 47.0h， 以47%的产率得到2-phenyl-3a,4,5,6,7,7a-hexahydro-benzooxazole
  参考文献：
  名称：

  Ring opening of aziridines by different fluorinating reagents: three synthetic routes to .alpha.,.beta.-fluoro amines with different stereochemical pathways

  摘要：

  DOI：

  10.1021/jo00337a024
• 作为产物：
  描述：

  7-benzoyl-7-aza-bicyclo[4.1.0]heptane 在 potassium fluoride 、 四丁基硫酸氢铵 作用下， 以 乙腈 为溶剂， 以91%的产率得到N-(2-fluorocyclohexyl)benzamide
  参考文献：
  名称：

  在Bu 4 NHSO 4存在下通过氮丙啶与二水合氟化钾反应轻松制备β-氟胺

  摘要：

  氟化钾与四硫酸氢四铵铵相结合是一种高效的试剂，可以高产率地将多种衍生自环状和无环烯烃的氮丙啶转化为β-氟胺衍生物。

  DOI：

  10.1021/jo034895k

文献信息

• Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis
  作者：Julia A. Kalow、Abigail G. Doyle

  DOI：10.1016/j.tet.2013.01.062

  日期：2013.7

  The enantioselective ring opening of aziridines using a latent source of HF is described. A combination of two Lewis acids, (salen)Co and an achiral Ti(IV) cocatalyst, provided optimal reactivity and enantioselectivity for the trans beta-fluoroamine product. The use of a chelating aziridine protecting group was crucial. Acyclic and cyclic meso N-picolinamide aziridines underwent fluoride ring opening in up to 84% ee, and the kinetic resolution of a piperidine-derived aziridine was performed with k(rel)=6.6. The picolinamide group may be readily removed without epimerization of the fluoroamine. Preliminary studies revealed a bimetallic mechanism wherein the chiral (salen)Co catalyst delivers the nucleophile and the Ti(IV) cocatalyst activates the aziridine. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines
  作者：Julia A. Kalow、Dana E. Schmitt、Abigail G. Doyle

  DOI：10.1021/jo300433a

  日期：2012.4.20

  Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide beta-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant beta-fluoroamine building blocks are presented.
• Synthesis of β-Fluoro Amides Using Partially Hydrated Nickel Difluoride as Fluorine Source
  作者：Wan Zhang、Li Su、Wei Hu、Jie Zhou

  DOI：10.1055/s-0032-1317157

  日期：——

  beta-Fluoro amides were obtained from the reactions of activated aziridines with partially hydrated nickel difluoride (NiF2 center dot nH(2)O, n < 4) in good yields (47-82%) in the presence of tetra-n-butylammonium fluoride (20 mol%), while the non-activated aziridines did not react under the same conditions.