2-(1-acetylamino-1-phenylmethyl)cyclohexanone | 151446-23-0

• 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: 2-(1-acetylamino-1-phenylmethyl)cyclohexanone
• 英文别名: N-{1-phenyl-1-[2-oxocyclohexyl]}acetamide；Acetamide, N-[(2-oxocyclohexyl)phenylmethyl]-；N-[(2-oxocyclohexyl)-phenylmethyl]acetamide
• CAS: 151446-23-0
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: FPOKYQWOOUHUDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C(Solv: ethyl acetate (141-78-6); heptane (142-82-5))
• 沸点：
  461.3±28.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-吗啉基-1-环己烯 、 N-(1-benzotriazoyl-1-phenylmethyl)acetamide 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以75%的产率得到2-(1-acetylamino-1-phenylmethyl)cyclohexanone
  参考文献：
  名称：

  Preparation of β-Amido Ketones and Aldehydes via Amidoalkylation of Enamines, Enol Silyl Ethers, and Vinyl Ethers

  摘要：

  Novel syntheses of beta-amidoalkyl ketones and aldehydes via amidoalkylations of enamines, silyl enol ethers, and vinyl. ethers with N-(1-benzotriazol-1-ylalkyl)amides are described.

  DOI：

  10.1021/jo990608u

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。
• Direct Amidoalkylation of Ketones
  作者：Wolter ten Hoeve、Hoeve Wynberg

  DOI：10.1080/00397919408011312

  日期：1994.3

  In a one-pot reaction aromatic aldehydes, urethane or acetamide and a variety of ketones condense in the presence of catalytic amounts of boron trifluoride or p-toluenesulfonic acid to furnish substituted carbamates or amides in good yield.
• Heteropoly acids as solid green Brønsted acids for a one-pot synthesis of β-acetamido ketones by Dakin–West reaction
  作者：Ezzat Rafiee、Fariba Tork、M. Joshaghani

  DOI：10.1016/j.bmcl.2005.11.080

  日期：2006.3

  An efficient improved procedure for the synthesis of beta-acetamido ketones has been developed by a heteropoly acid (HPA) catalyzed three-component coupling protocol. The present methodology offers several advantages such as excellent yields, simple procedure, short reaction times, and mild conditions. (C) 2005 Elsevier Ltd. All rights reserved.
• Iqbal, Javed; Mukhopadhyay, Manoj; Das, Bhaskar C., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1997, vol. 36, # 6, p. 498 - 506
  作者：Iqbal, Javed、Mukhopadhyay, Manoj、Das, Bhaskar C.、Rajesh、De, Asit、Sanghi, Rashmi、Jain, Swati、Nandy, Jyoti P.

  DOI：——

  日期：——
• Omarov, T. T.; Gubasheva, A. Sh.; Sultanbaeva, B. M., Russian Journal of Organic Chemistry, 1992, vol. 28, # 10.2, p. 1784 - 1785
  作者：Omarov, T. T.、Gubasheva, A. Sh.、Sultanbaeva, B. M.

  DOI：——

  日期：——