N-(4-fluorophenyl)-N-phenyladamantane-1-carboxamide

• 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-(4-fluorophenyl)-N-phenyladamantane-1-carboxamide
• 化学式: C₂₃H₂₄FNO
• 分子量: 349.448
• InChiKey: JCLPRSCJHIUKCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  频哪醇 、 N-(4-fluorophenyl)-N-phenyladamantane-1-carboxamide 、 三溴化硼 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到N-(4-fluorophenyl)-N-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)adamantane-1-carboxamide
  参考文献：
  名称：

  C–H Borylation of Diphenylamines through Adamantane-1-carbonyl Auxiliary by BBr₃

  摘要：

  A method for ortho-C-H borylation of diphenylamines using BBr3 as the boron source has been reported. The noncatalytic adamantane-1-carbonyl directed reaction exhibited site exclusivity and good functional group tolerance. Generally, the borylation occurred at the more electron-rich aromatic ring and the borylated products could be converted to various useful intermediates. Besides, the derived arylation and removal of auxiliary of the product could be achieved in a one-pot fashion.

  DOI：

  10.1021/acs.orglett.0c02552
• 作为产物：
  描述：

  4-氟二苯基胺 、 金刚烷酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N-(4-fluorophenyl)-N-phenyladamantane-1-carboxamide
  参考文献：
  名称：

  C–H Borylation of Diphenylamines through Adamantane-1-carbonyl Auxiliary by BBr₃

  摘要：

  A method for ortho-C-H borylation of diphenylamines using BBr3 as the boron source has been reported. The noncatalytic adamantane-1-carbonyl directed reaction exhibited site exclusivity and good functional group tolerance. Generally, the borylation occurred at the more electron-rich aromatic ring and the borylated products could be converted to various useful intermediates. Besides, the derived arylation and removal of auxiliary of the product could be achieved in a one-pot fashion.

  DOI：

  10.1021/acs.orglett.0c02552

文献信息

• C–H Borylation of Diphenylamines through Adamantane-1-carbonyl Auxiliary by BBr₃
  作者：Gaorong Wu、Xiaopan Fu、Yangyang Wang、Kezuan Deng、Lili Zhang、Tao Ma、Yafei Ji

  DOI：10.1021/acs.orglett.0c02552

  日期：2020.9.4

  A method for ortho-C-H borylation of diphenylamines using BBr3 as the boron source has been reported. The noncatalytic adamantane-1-carbonyl directed reaction exhibited site exclusivity and good functional group tolerance. Generally, the borylation occurred at the more electron-rich aromatic ring and the borylated products could be converted to various useful intermediates. Besides, the derived arylation and removal of auxiliary of the product could be achieved in a one-pot fashion.