N-[3-(4-氯苯基)-3-氧代-1-苯基丙基]乙酰胺 | 850582-21-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: N-[3-(4-氯苯基)-3-氧代-1-苯基丙基]乙酰胺
• 英文名称: N-(3-(4-chlorophenyl)-3-oxo-1-phenylpropyl)acetamide
• 英文别名: N-[3-(4-chlorophenyl)-3-oxo-1-phenylpropyl]acetamide
• CAS: 850582-21-7
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: ARDQYQHWCPOWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-[3-(4-氯苯基)-3-氧代-1-苯基丙基]乙酰胺 在 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到rac-((4R,5S)-4-chlorophenyl)(2-methyl-4-phenyl-4,5-dihydrooxazol-5-yl)methanone
  参考文献：
  名称：

  Electrosynthesis of Trisubstituted 2-Oxazolines via Dehydrogenative Cyclization of β-Amino Arylketones

  摘要：

  An electrochemically intramolecular functionalization of C-(sp(3))-H bonds with masked oxygen nucleophiles was developed. With IU as the catalyst and electrolyte, diverse trisubstituted 2-oxazolines were constructed in good to excellent yields. This newly developed electrochemical dehydrogenalive approach features external oxidant-free and additive-free conditions.

  DOI：

  10.1021/acs.orglett.8b00165
• 作为产物：
  描述：

  对氯苯乙酮 、 苯甲醛 、 乙酰氯 在 乙腈 作用下， 反应 0.5h， 以75%的产率得到N-[3-(4-氯苯基)-3-氧代-1-苯基丙基]乙酰胺
  参考文献：
  名称：

  Simple and New Method for the Synthesis of β-Acetamido Ketones on a Solid Surface

  摘要：

  [image omitted] Borax/POCl3(BPO) was found to be an efficient reagent for the preparation of various -acetamido ketones by a one-pot reaction of aryl aldehydes, enolisable ketones, acetyl chloride, and acetonitrile in a solvent-free medium. The present methodology offers several advantages, such as a cheaper process, good to excellent yields, simple procedure, short reaction times, and easy workup.

  DOI：

  10.1080/00397911.2010.492459

文献信息

• Synthesis of Mannich type products via a three-component coupling reaction
  作者：Ghanshyam Pandey、Ravi P. Singh、Ashish Garg、Vinod K. Singh

  DOI：10.1016/j.tetlet.2005.01.118

  日期：2005.3

  The reactions of alkyl nitriles, acetyl chloride, aldehydes and β-ketoesters or simple ketones was studied for the one-pot synthesis of β-acetamido carbonyl compounds. It was observed that the reaction proceeds in the absence of Lewis acids. However, a Lewis acid catalyzes the reaction and several were tested. It was found that whereas Cu(OTf)2 is suitable for the coupling of β-ketoesters with aldehydes

  为一锅法合成β-乙酰氨基羰基化合物，研究了烷基腈，乙酰氯，醛和β-酮酸酯或简单酮的反应。观察到反应在不存在路易斯酸的情况下进行。但是，路易斯酸催化该反应，并对其进行了测试。发现Cu（OTf）2适合将β-酮酸酯与醛偶联，而Sc（OTf）3最适合酮。根据中间体的分离和表征，提出了一种可能的机制。
• Simple and Efficient Procedure for the One‐Pot Synthesis of β‐Acetamido‐β‐aryl‐propiophenones by Molecular Iodine–Catalyzed Tandem Reaction
  作者：M. A. Pasha、V. P. Jayashankara、N. Ramachandraswamy

  DOI：10.1080/00397910701234982

  日期：2007.5

  Abstract Molecular iodine efficiently catalyzes the four‐component tandem reaction of araldehydes, arylmethyl ketones, acetyl chloride, and acetonitrile to afford the corresponding β‐acetamido‐β‐aryl‐propiophenones. The new protocol gives high yields of the products, and the reactions go to completion within 10–15 min on a hot plate at 80–85°C.

  摘要 分子碘可有效催化芳醛、芳甲基酮、乙酰氯和乙腈的四组分串联反应，得到相应的 β-乙酰氨基-β-芳基苯丙酮。新方案提供了高产率的产品，反应在 80-85°C 的热板上在 10-15 分钟内完成。
• Zinc oxide as an economical and efficient catalyst for the one-pot preparation of β-acetamido ketones via a four-component condensation reaction
  作者：Malek Taher Maghsoodlou、Asadollah Hassankhani、Hamid Reza Shaterian、Sayyed Mostafa Habibi-Khorasani、Elaheh Mosaddegh

  DOI：10.1016/j.tetlet.2007.01.060

  日期：2007.3

  A new, efficient, one-pot, four-component condensation of benzaldehyde derivatives, acetophenone derivatives, acetyl chloride and acetonitrile in the presence of zinc oxide as catalyst is described for the synthesis of β-acetamido ketones.

  描述了在氧化锌作为催化剂存在下，苯甲醛衍生物，苯乙酮衍生物，乙酰氯和乙腈的新型，高效，一锅四组分缩合反应，用于合成β-乙酰氨基酮。
• A modified procedure for the Dakin–West reaction: an efficient and convenient method for a one-pot synthesis of β-acetamido ketones using silica sulfuric acid as catalyst
  作者：Mohammd M. Khodaei、Ahmad R. Khosropour、Peyman Fattahpour

  DOI：10.1016/j.tetlet.2005.01.149

  日期：2005.3

  A one-pot, four-component condensation of an aryl aldehyde, an aryl ketone, acetyl chloride and acetonitrile in the presence of silica sulfuric acid as an active, inexpensive, recoverable and recyclable catalyst is disclosed for the synthesis of β-acetamido ketones.

  公开了在二氧化硅硫酸存在下作为活性，廉价，可回收和可循环使用的催化剂的一锅，四组分缩合的芳基醛，芳基酮，乙酰氯和乙腈，用于合成β-乙酰氨基酮。
• One‐Pot, Four‐Component Reaction of Aryl Aldehydes, Aryl Ketones, Phosphorus Trichloride, and Acetonitrile Catalyzed by Acetyl Chloride: Synthesis of<i>β</i>‐Acetamido Ketones
  作者：Mohammad Anary‐Abbasinejad、Azimeh Saidipoor

  DOI：10.1080/00397910701767064

  日期：2008.1.1

  Abstract The one‐pot, four‐component reaction of aryl aldehydes, aryl ketones, phosphorus trichloride, and acetonitrile, catalyzed by acetyl chloride, affords β‐acetamido ketones in good to excellent yields. Silicaphosphine (silphos), [P(Cl)3‐n(SiO2)n], can also be used effectively as a solid‐supported reagent instead of phosphorus trichloride.

  摘要 芳基醛、芳基酮、三氯化磷和乙腈的一锅四组分反应，在乙酰氯的催化下，以良好到优异的收率得到 β-乙酰氨基酮。Silicaphosphine (silphos)，[P(Cl)3-n(SiO2)n]，也可以有效地用作固体负载试剂代替三氯化磷。