N-Chlor-m-methoxybenzamid | 33341-67-2

• 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-Chlor-m-methoxybenzamid
• 英文别名: N-Chlor-3-methoxy-benzamid；N-chloro-3-methoxybenzamide
• CAS: 33341-67-2
• 化学式: C₈H₈ClNO₂
• 分子量: 185.61
• InChiKey: LXDBQTKOFNEAMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Chlor-m-methoxybenzamid 在 N-甲基吡咯 、 二氯乙酸 作用下， 以 氯仿 为溶剂， 生成 3-甲氧基苯甲酰胺
  参考文献：
  名称：

  The use of an electrophile carrier to determine the number of intermediates in the chlorination of 1-methylpyrrole

  摘要：

  A kinetic and product study of the dichloroacetic acid catalyzed chlorination of 1-methylpyrrole with 3- and 4-substituted N-chlorobenzamides was carried out. Protonated N-chlorobenzamides served as carriers of Cl+. A Hammett correlation was obtained with p=-0.68 (r=0.98, n=8). General acid catalysis was observed with alpha=0.48 (r=0.99 and n=7). The yields of 2-chlorination (84+/-0.7%) and 3-chlorination (2.6+/-0.4%) were essentially constant (constant intramolecular selectivity) as the substituent on the N-chlorobenzamide was varied. Observation of constant intramolecular selectivity indicated that two intermediates were formed during the acid catalyzed chlorination of 1-methylpyrrole with N-chlorobenzamides. The carrier method is applicable to all types of aromatic systems and limited only by the availability of suitable carrier molecules. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00187-x

文献信息

• Cobalt(III)-Catalyzed C–H Activation/Annulation Cascade Reaction of N-Chlorobenzamides with 2-Acetylenic Ketones at Room Temperature
  作者：Yong Wu、Zhouping Wu、Qinwen Zheng、Guanghui Lv、Ruizhi Lai、Yao Hu、Li Hai

  DOI：10.1055/a-1794-1314

  日期：2022.7

  N-chlorobenz­amides with 2-acetylenic ketones at room temperature is reported. This reaction sets N–Cl bond of N-chlorobenzamide as an internal oxidant, displaying broad functional group tolerance and excellent reverse selectivity of alkyne insertion under mild and safe conditions. The cascade reaction offers a straightforward and mild protocol to construct isoquinolones in high yields at room temperature

  报道了在室温下Co(III) 催化的N-氯苯甲酰胺与 2-炔酮的温和级联环化。该反应将 N-氯苯甲酰胺的N -Cl 键设置为内氧化剂，在温和安全的条件下表现出广泛的官能团耐受性和出色的炔烃插入反向选择性。级联反应提供了一种简单而温和的方案，可在室温下以高产率构建异喹诺酮类药物。
• Reverse Regioselective Cp*Co(III)-Catalyzed [4 + 2] C–H Annulation of <i>N</i>-Chloroamides with Vinylsilanes: Synthesis of 4-Silylated Isoquinolones and Their Synthetic Utilities
  作者：Arijit Ghosh、Tamanna Rana、Nilanjan Bhaduri、Amit B. Pawar

  DOI：10.1021/acs.orglett.3c03115

  日期：2023.11.3

  have developed a Cp*Co(III)-catalyzed reverse regioselective [4 + 2] annulation of N-chlorobenzamides/acrylamides with vinylsilanes for the synthesis of 4-silylated isoquinolones. The reaction was performed at ambient temperature under redox-neutral conditions. The reaction utilized the N–Cl bond as an internal oxidant, furnished the required products with excellent regioselectivities, and demonstrated

  我们开发了一种 Cp*Co(III) 催化的N-氯苯甲酰胺/丙烯酰胺与乙烯基硅烷的反向区域选择性 [4 + 2] 成环反应，用于合成 4-甲硅烷基化异喹诺酮。该反应在环境温度、氧化还原中性条件下进行。该反应利用N-Cl键作为内氧化剂，使所需产物具有优异的区域选择性，并表现出高官能团耐受性。4-硅烷化异喹诺酮的合成效用已被证明可用于通过无金属 C-C 偶联制备 4-杂芳基化和 4-烷基化异喹诺酮。此外，通过 4-甲硅烷基化异喹诺酮的原脱甲硅烷基化合成了 3,4-二氢异喹诺酮，从而使乙烯基硅烷成为乙烯替代品。