N-(4-fluoro-3-chlorophenyl)pivalamide | 188787-17-9

• 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-fluoro-3-chlorophenyl)pivalamide
• 英文别名: N-pivaloyl-3-chloro-4-fluoroaniline；N-(3-chloro-4-fluorophenyl)-2,2-dimethylpropanamide
• CAS: 188787-17-9
• 化学式: C₁₁H₁₃ClFNO
• mdl: MFCD01182234
• 分子量: 229.682
• InChiKey: KNSYHWQPYVPIGB-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C(Solv: hexane (110-54-3))
• 沸点：
  348.6±32.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 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-(4-fluoro-3-chlorophenyl)pivalamide 在 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 2.0h， 生成 6-氟-7-甲基-2-(2-甲基-2-丙基)-1,3-苯并恶唑
  参考文献：
  名称：

  Ortho Lithiation of N-Pivaloylfluoroanilines as a Useful Tool for Either Selective Methylation or Benzoxazole Synthesis

  摘要：

  Lithiation of N-pivaloyl-3,4-difluoroaniline (1a) with a slight excess of 2 mole equiv of n-butyllithium followed by methylation was studied. The reaction was found to be useful for either the selective methylation of 3,4-difluoroaniline or the synthesis of benzoxazole derivatives, depending on the reaction temperature. In the reaction of N-pivaloyl-3-chloro-4-fluoroaniline (1b) and N-pivaloyl-3-fluoroaniline (1c), the reaction proceeded rather sluggishly but benzoxazole formation predominated.

  DOI：

  10.1021/op0498969
• 作为产物：
  描述：

  N-(3-氯苯基)棕榈酰胺 在 二(叔丁基羰基氧基)碘苯 、 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以55%的产率得到N-(4-fluoro-3-chlorophenyl)pivalamide
  参考文献：
  名称：

  Hypervalent Iodine Mediated para-Selective Fluorination of Anilides

  摘要：

  A metal-free method for the direct regioselective fluorination of anilides has been developed. In the presence of bis(tert-butylcarbonyloxy)iodobenzene (PhI(OPiv)(2)) and hydrogen fluoride-pyridine, the para-fluorination products of anilides were obtained in moderate to good yields. Because of its operational safety and the use of readily available reagents, this new procedure provides facile access to a variety of para-fluorinated anilides.

  DOI：

  10.1021/jo302099d

文献信息

• A Multistep Flow Process for the Synthesis of Highly Functionalized Benzoxazoles
  作者：Jörg Sedelmeier、Fabio Lima、Alain Litzler、Benjamin Martin、Francesco Venturoni

  DOI：10.1021/ol402706a

  日期：2013.11

  An efficient and scalable transformation of 3-halo-N-acyl anilines to the corresponding benzoxazoles within a continuous flow reactor is reported. This transformation proceeds via base-mediated deprotonation, ortho-lithiation, and intramolecular cyclization to provide unstable lithiated benzoxazole moieties. The subsequent in-line electrophilic quench results in the formation of substituted benzoxazoles in high yield and quality. Continuous flow technology allowed for accurate temperature control and immediate in-line quench while minimizing the hold-up time for the unstable lithiated intermediates thereby minimizing associated byproduct formation.
• SEPIAPTERIN REDUCTASE INHIBITORS
  申请人：QUARTET MEDICINE, INC.

  公开号：US20170096435A1

  公开（公告）日：2017-04-06

  Inhibitors of sepiapterin reductase and uses of sepiapterin reductase inhibitors in analgesia, treatment of acute and chronic pain, anti-inflammation, and immune cell regulation are disclosed.
• US9963462B2
  申请人：——

  公开号：US9963462B2

  公开（公告）日：2018-05-08
• Ortho Lithiation of <i>N</i>-Pivaloylfluoroanilines as a Useful Tool for Either Selective Methylation or Benzoxazole Synthesis
  作者：Yasuo Yoshida、Yusuke Hamada、Kazuto Umezu、Fumiya Tabuchi

  DOI：10.1021/op0498969

  日期：2004.11.1

  Lithiation of N-pivaloyl-3,4-difluoroaniline (1a) with a slight excess of 2 mole equiv of n-butyllithium followed by methylation was studied. The reaction was found to be useful for either the selective methylation of 3,4-difluoroaniline or the synthesis of benzoxazole derivatives, depending on the reaction temperature. In the reaction of N-pivaloyl-3-chloro-4-fluoroaniline (1b) and N-pivaloyl-3-fluoroaniline (1c), the reaction proceeded rather sluggishly but benzoxazole formation predominated.
• Hypervalent Iodine Mediated <i>para</i>-Selective Fluorination of Anilides
  作者：Tian Tian、Wen-He Zhong、Shuai Meng、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1021/jo302099d

  日期：2013.1.18

  A metal-free method for the direct regioselective fluorination of anilides has been developed. In the presence of bis(tert-butylcarbonyloxy)iodobenzene (PhI(OPiv)(2)) and hydrogen fluoride-pyridine, the para-fluorination products of anilides were obtained in moderate to good yields. Because of its operational safety and the use of readily available reagents, this new procedure provides facile access to a variety of para-fluorinated anilides.