3-氯-N-苯基苯甲酰胺 | 6832-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氯-N-苯基苯甲酰胺
• 英文名称: 3-chloro-N-phenylbenzamide
• 英文别名: N-(phenyl)-3-chlorobenzamide
• CAS: 6832-92-4
• 化学式: C₁₃H₁₀ClNO
• mdl: MFCD00045191
• 分子量: 231.681
• InChiKey: QDIUKUHOHYCIRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  3-氯-N-苯基苯甲酰胺 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 53.5h， 生成 2-Benzyl-3-chlor-benzoesaeure
  参考文献：
  名称：

  Application of organolithium and related reagents in synthesis XVI: Synthetic strategies based on aromatic metallation. A concise regiospecific conversion of chlorobenzoic acids into their benzylated derivatives

  摘要：

  The reaction of benzyl bromide with bis-(N- and C-ortho)-lithiated chloroanilides 4, 5, and 6 has been examined. It has been found that in the case where the lithiated compound was derived from meta-methoxyanilides, pre-addition of LiBr or TMEDA was required to achieve C-benzylation. These results were accounted for by the conversion of the usually formed dimer into a mixed dimer with the LiBr or TMEDA complex in which the C-lithium bond appears to be more accessible towards electrophiles. The practical synthesis of o-benzylchlorobenzoic acids 10, 11, and 12 was accomplished via ionic reductive cleavage (Et(3)SiH/TiCl4) of the corresponding phthalides 18, 19, and 20. The acids 10, 11b, and 11c afforded the corresponding anthrones, upon treatment with trifluoroacetic anhydride which were oxidized by chromium trioxide to the new chloroantraquinones 21, 22, and 23.

  DOI：

  10.1007/bf00817261
• 作为产物：
  描述：

  3-氯二苯甲酮 以 甲醇 为溶剂， 生成 3-氯-N-苯基苯甲酰胺
  参考文献：
  名称：

  Joshi, Vidya; Sharma, R. K., Journal of the Indian Chemical Society, 1988, vol. 65, # 8, p. 564 - 566

  摘要：

  DOI：

文献信息

• Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
  作者：Yu-Chao Yuan、Raghu Kamaraj、Christian Bruneau、Thierry Labasque、Thierry Roisnel、Rafael Gramage-Doria

  DOI：10.1021/acs.orglett.7b03278

  日期：2017.12.1

  The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.

  使用钌催化剂，以高收率和较短的反应时间实现了单步操作中各种合成吸引力的邻苯二甲酰亚胺前所未有的转化为酰胺。机理研究表明，独特的均质途径涉及五元环的打开和CO 2的释放，其中水是质子的来源。
• Anilinolysis of Picryl Benzoate Derivatives in Methanol: Reactivity, Regioselectivity, Kinetics, and Mechanism
  作者：Mahmoud F. Ibrahim、Mohamed A. El-Atawy、Samir K. El-Sadany、Ezzat A. Hamed

  DOI：10.1002/kin.20779

  日期：2013.9

  The reaction of picryl benzoate derivatives 1a–g with aniline in methanol proceeds through COO and ArO bond cleavage pathways. Furthermore, the reactivity of these esters toward anilinolysis is correlated to the energy gap between highest occupied molecular orbital aniline and lowest unoccupied molecular orbital of each ester. The regioselectivity of acyloxygen versus aryloxygen cleavage is also

  甲醇中苯甲酸吡啶酯衍生物1a–g与苯胺在甲醇中的反应通过COO和ArO键的裂解途径进行。此外，这些酯对苯胺分解的反应性与每个酯的最高占据分子轨道苯胺和最低未占据分子轨道之间的能隙相关。还讨论了酰基氧对芳基氧裂解的区域选择性。整体速率常数ķ TOT分成ķ CO  Ô（酰基-氧裂解速率常数）和ķ氩 Ò（芳基氧裂解速率常数）。该CO 通过逐步机制O键裂解的进步，其中所述四面体中间体的形成是限速步骤。上述Ar  O键裂解继续通过A S Ñ其中所述离去基团从所述迈森海梅复杂离开其在速率决定步骤形成后迅速发生的Ar机制。
• Clickable coupling of carboxylic acids and amines at room temperature mediated by SO₂F₂: a significant breakthrough for the construction of amides and peptide linkages
  作者：Shi-Meng Wang、Chuang Zhao、Xu Zhang、Hua-Li Qin

  DOI：10.1039/c9ob00699k

  日期：——

  carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in

  酰胺键和肽键的构建是所有生命过程和有机合成中最基本的转变之一。结构无处不在的酰胺基序的合成对于许多重要分子（如肽，蛋白质，生物碱，药剂，聚合物，配体和农用化学品）的组装至关重要。开发了一种SO2F2介导的羧酸与胺的直接可点击偶合方法，以简单，温和，高效，稳健和实用的方式合成各种酰胺（> 110例，大多数情况下> 90％的收率） ）。
• Cu-Mediated Synthesis of Indolines and Dihydroisoquinolinones through Arylperfluoroalkylation of Unactivated Alkenes
  作者：Dandan Li、Yan Wang、Zhenzhen Jia、Zhaocheng Ou、Yongrui Dong、Cunjie Lv、Guangbin Fu、Deqiang Liang

  DOI：10.1002/ejoc.201900680

  日期：2019.8.15

  The copper‐mediated fluroalkylation/cyclization of N‐allyl anilines has been described with unactivated double bonds as the radical acceptor. The reaction provides an efficient and direct access to 3‐fluoroalkyl indolines in moderate to good yields. This protocol combines a simple experimental procedure with low‐costing fluoroalkylated sources and excellent functional group tolerance.

  N-烯丙基苯胺的铜介导的氟烷基化/环化已被描述为以未激活的双键为自由基受体。该反应以中等到良好的收率提供了直接和有效的3-氟烷基二氢吲哚的途径。该协议结合了简单的实验程序和低成本的氟代烷基化来源以及出色的官能团耐受性。
• PROCESS FOR ALKENYLATING CARBOXAMIDES
  申请人：Staffel Wolfgang

  公开号：US20090131657A1

  公开（公告）日：2009-05-21

  The present invention relates to a process for preparing N-(1-alkenyl)carboxamides of the formula I, which comprises reacting a carboxamide of the formula II with an alkyne of the formula III in the presence of a catalyst selected from among carbonyl complexes, halides and oxides of rhenium, manganese, tungsten, molybdenum, chromium and iron.

  本发明涉及一种制备式I的N-(1-烯基)羧酰胺的方法，包括在选择自铼、锰、钨、钼、铬和铁的羰基配合物、卤化物和氧化物之一作为催化剂的情况下，将式II的羧酰胺与式III的炔烃反应。