N-(2-benzoyl-5-chlorophenyl)acetamide | 34999-47-8

• 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-(2-benzoyl-5-chlorophenyl)acetamide
• 英文别名: 2-Acetamido-4-chlorbenzophenon
• CAS: 34999-47-8
• 化学式: C₁₅H₁₂ClNO₂
• 分子量: 273.719
• InChiKey: ZOOMKNFFJWHKHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  108-118 °C
• 沸点：
  501.5±45.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-benzoyl-5-chlorophenyl)acetamide 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 生成 7-chloro-4-phenyl-1,4-dihydro-benzo[d][1,3]thiazine-2-thione
  参考文献：
  名称：

  Lednicer,D.; Emmert,D.E., Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 903 - 910

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氯苯胺 在 叔丁基过氧化氢 、 三氟甲磺酸 、 palladium diacetate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 5.0h， 生成 N-(2-benzoyl-5-chlorophenyl)acetamide
  参考文献：
  名称：

  钯催化苯乙醇对乙酰苯胺的氧化CH键酰化反应

  摘要：

  通过在三氟甲磺酸（TfOH）存在下用乙酸钯催化的过氧化氢叔丁基酯（TBHP）作为氧化剂，通过乙酰苯胺与苄醇的酰化反应，开发了一种构建CC键的有效且清洁的方法。酰化反应显示出优异的反应性，并且在最佳条件下可获得高达95％的相应芳基酮收率。

  DOI：

  10.1002/adsc.201100417

文献信息

• A one-pot process for palladium catalyzed direct C–H acylation of anilines in water using a removable ortho directing group
  作者：Fruzsina Szabó、Dániel Simkó、Zoltán Novák

  DOI：10.1039/c3ra45160g

  日期：——

  A new mild, practical method for the synthesis of aminobenzophenone derivatives through a three step one-pot reaction sequence involving acylation of anilines, palladium catalyzed cross-dehydrogenative coupling of the formed anilides and the hydrolytic cleavage is reported. The full reaction sequence was performed under aqueous conditions.

  报道了一种新的温和，实用的方法，该方法通过三步一锅法反应合成氨基二苯甲酮衍生物，该反应涉及苯胺的酰化，钯催化形成的酸酐的交叉脱氢偶联和水解裂解。完整的反应顺序在水性条件下进行。
• Palladium-Catalyzed Direct <i>ortho</i>-Acylation through an Oxidative Coupling of Acetanilides with Toluene Derivatives
  作者：Zhangwei Yin、Peipei Sun

  DOI：10.1021/jo302125h

  日期：2012.12.21

  A facile ortho-acylation of acetanilides by a Pd-catalyzed oxidative C–H activation was developed in which low toxic, stable, and commercially available toluene derivatives were first used as acylation reagents by a tandem reaction to form o-acylacetanilides with moderate to good yields. Inexpensive, safe, and environmentally benign TBHP was proved to be an effective oxidant for these transformations

  一种简便邻通过Pd催化的氧化C-H活化乙酰苯胺的酰化被开发，其中低毒性的，稳定的，并且可商购的甲苯衍生物通过串联式反应首先用作酰化试剂以形成ö -acylacetanilides具有中度至良好产量。廉价，安全和环境友好的TBHP被证明是这些转化的有效氧化剂。
• Mild Palladium-Catalyzed Oxidative Direct<i>ortho-</i>CH Acylation of Anilides under Aqueous Conditions
  作者：Fruzsina Szabó、János Daru、Dániel Simkó、Tibor Zs. Nagy、András Stirling、Zoltán Novák

  DOI：10.1002/adsc.201200948

  日期：2013.3.11

  Palladium‐catalyzed cross‐dehydrogenative coupling between anilides and aromatic aldehydes was achieved under aqueous conditions. A wide variety of the desired benzophenone derivatives was isolated in good to excellent yield. The reaction rate acceleration effect of acid and detergent has been demonstrated. Mechanistic insight has been obtained from quantum chemical calculations.

  在水性条件下，实现了钯催化的苯甲酸酯和芳族醛之间的交叉脱氢偶联。以良好至优异的产率分离出各种所需的二苯甲酮衍生物。已经证明了酸和去污剂的反应速率加速作用。从量子化学计算中已经获得了机械学的见解。
• Room Temperature Palladium-Catalyzed Decarboxylative <i>ortho</i>-Acylation of Acetanilides with α-Oxocarboxylic Acids
  作者：Ping Fang、Mingzong Li、Haibo Ge

  DOI：10.1021/ja105245f

  日期：2010.9.1

  A novel Pd-catalyzed decarboxylative ortho-acylation of acetanilides with alpha-oxocarboxylic acids is realized at room temperature. This reaction provides efficient access to o-acyl acetanilides under mild conditions.
• Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C–C-Coupling Reactions
  作者：Bernd Schmidt、Nelli Elizarov、Uwe Schilde、Alexandra Kelling

  DOI：10.1021/acs.joc.5b00272

  日期：2015.5.1

  The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles.