N-((1R,2R)-2-fluorocyclohexyl)picolinamide | 1443674-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-((1R,2R)-2-fluorocyclohexyl)picolinamide
• 英文别名: N-[(1R,2R)-2-fluorocyclohexyl]pyridine-2-carboxamide
• CAS: 1443674-24-5
• 化学式: C₁₂H₁₅FN₂O
• 分子量: 222.262
• InChiKey: MVTWMQLQPXAYMF-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 N-((1R,2R)-2-fluorocyclohexyl)picolinamide 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以95%的产率得到tert-butyl ((1R,2R)-2-fluorocyclohexyl)(picolinoyl)carbamate
  参考文献：
  名称：

  Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.01.062
• 作为产物：
  描述：

  7-氮杂双环[4.1.0]庚烷 在 tetrakis(dimethylamido)titanium(IV) 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 (R, R)-(salen)Co(II) 、 六氟异丙醇 、 苯甲酰氟 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 34.0h， 生成 N-((1R,2R)-2-fluorocyclohexyl)picolinamide
  参考文献：
  名称：

  Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.01.062

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.