N-tert-Butyl-3,5-dichlorbenzamid | 33244-96-1

• 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-tert-Butyl-3,5-dichlorbenzamid
• 英文别名: N-(tert-butyl)-3,5-dichlorobenzamide；N-tert-butyl-3,5-dichlorobenzamide
• CAS: 33244-96-1
• 化学式: C₁₁H₁₃Cl₂NO
• mdl: MFCD02666639
• 分子量: 246.136
• InChiKey: GIZJFYDJGULERU-UHFFFAOYSA-N

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：
  1

反应信息

• 作为反应物：
  描述：

  N-tert-Butyl-3,5-dichlorbenzamid 在 四丁基高氯酸铵 、 sodium hydride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.83h， 生成 methyl tert-butyl(2-(3,5-dichlorophenyl)-4,4,4-trifluorobutyl)carbamate
  参考文献：
  名称：

  Electrochemically‐Driven 1,4‐Aryl Migration via Radical Fluoromethylation of N‐allylbenzamides: a Straightforward Access to Functionalized β‐Arylethylamines

  摘要：

  An electrochemical radical Truce Smiles rearrangement of N‐allylbenzamides is documented herein. The selective 1,4‐aryl migration was triggered by the radical fluoromethylation of the alkene providing a direct route to fluoro derivatives of the highly privileged β‐arylethylamine pharmacophore. This practical transformation utilizes readily available starting materials and employs an electrical current to drive the oxidative process under mild reaction conditions. It accommodates a variety of migratory aryl groups with different electronic properties and substitution patterns. Careful selection of the protecting group on the nitrogen atom of the N‐allylbenzamide is crucial to outcompete the undesired 6‐endo cyclization and achieve high level of selectivity towards the 1,4‐aryl migration. DFT calculations support the reaction mechanism and unveil the origin of selectivity between the two competitive pathways.

  DOI：

  10.1002/anie.202406017
• 作为产物：
  描述：

  3,5-二氯苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-tert-Butyl-3,5-dichlorbenzamid
  参考文献：
  名称：

  Electrochemically‐Driven 1,4‐Aryl Migration via Radical Fluoromethylation of N‐allylbenzamides: a Straightforward Access to Functionalized β‐Arylethylamines

  摘要：

  An electrochemical radical Truce Smiles rearrangement of N‐allylbenzamides is documented herein. The selective 1,4‐aryl migration was triggered by the radical fluoromethylation of the alkene providing a direct route to fluoro derivatives of the highly privileged β‐arylethylamine pharmacophore. This practical transformation utilizes readily available starting materials and employs an electrical current to drive the oxidative process under mild reaction conditions. It accommodates a variety of migratory aryl groups with different electronic properties and substitution patterns. Careful selection of the protecting group on the nitrogen atom of the N‐allylbenzamide is crucial to outcompete the undesired 6‐endo cyclization and achieve high level of selectivity towards the 1,4‐aryl migration. DFT calculations support the reaction mechanism and unveil the origin of selectivity between the two competitive pathways.

  DOI：

  10.1002/anie.202406017

文献信息

• Substituted pyrazole compounds useful as soluble epoxide hyrolase inhibitors
  申请人：Fleck Roman Wolfgang

  公开号：US20090227588A1

  公开（公告）日：2009-09-10

  Disclosed are compounds active against soluble epoxide hydrolase (sEH), compositions thereof and methods of using and making same.

  本发明涉及对可溶性环氧水解酶（sEH）活性的化合物，其组成物和使用和制备它们的方法。
• [EN] INSECTICIDAL BENZENEDICARBOXAMIDE DERIVATIVE<br/>[FR] DÉRIVÉ DE BENZÈNEDICARBOXAMIDE INSECTICIDE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2010012442A2

  公开（公告）日：2010-02-04

  The present invention relates to a novel benzenedicarboxamide derivative and the use thereof as an insecticide having the formula (I) wherein the chemical groups W1 to W9, and R1 to R3 are as defined herein.