N-[2-acetyl-1-(4-nitrophenyl)-3-oxo-butyl]acetamide | 170034-47-6

• 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-acetyl-1-(4-nitrophenyl)-3-oxo-butyl]acetamide
• 英文别名: N-[2-Acetyl-1-(4-nitrophenyl)-3-oxobutyl]acetamide
• CAS: 170034-47-6
• 化学式: C₁₄H₁₆N₂O₅
• 分子量: 292.291
• InChiKey: KRACWMTXJRMTSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 乙腈 、 乙酰丙酮 在 氯氧化铋 乙酰氯 作用下， 反应 12.0h， 以57%的产率得到N-[2-acetyl-1-(4-nitrophenyl)-3-oxo-butyl]acetamide
  参考文献：
  名称：

  Bismuth(III) Oxychloride Procatalyst Based One-Pot Multicomponent Synthesis of β′-Acetamido-β-dicarbonyl Compounds with Special Reference to pref-β′-Acetamido-β-oxo Esters

  摘要：

  由原催化剂氯氧化铋(III) 和乙酰氯原位生成的氯化铋(III) 有效催化从醛、烯醇化β-二酮或β-氧代酯和β-氧代酯中一锅法合成β′-乙酰氨基-β-二羰基化合物。乙酰氯的乙腈溶液，在无溶剂条件下，室温；就β-氧代酯衍生产品而言，这些产品具有中等至优异的非对映选择性，有利于预异构体。一种预-β′-乙酰氨基-β-氧代酯的X射线晶体学分析显示了三维超分子组装体中的C-H…O和N-H…O分子间相互作用。

  DOI：

  10.1055/s-2006-958955

文献信息

• Bismuth(III) Oxychloride Procatalyst Based One-Pot Multicomponent Synthesis of β′-Acetamido-β-dicarbonyl Compounds with Special Reference to <i>pref</i>-β′-Acetamido-β-oxo Esters
  作者：Rina Ghosh、Swarupananda Maiti、Soumen Ghosh、Alok Mukherjee

  DOI：10.1055/s-2006-958955

  日期：2007.1

  Bismuth(III) chloride generated in situ from the procatalyst bismuth(III) oxychloride and acetyl chloride efficiently catalyzes the one-pot synthesis of β′-acetamido-β-dicarbonyl compounds from aldehydes, enolizable β-diketones, or β-oxo esters and acetyl chloride in acetonitrile solution and under solvent-free conditions at room temperature; in the case of the β-oxo ester derived products, these are obtained with moderate to excellent dia­stereoselectivity in favor of the pref-isomer. X-ray crystallographic analysis of one pref-β′-acetamido-β-oxo ester exhibits C-H···O and N-H···O intermolecular interactions in the three-dimensional supramolecular assembly.

  由原催化剂氯氧化铋(III) 和乙酰氯原位生成的氯化铋(III) 有效催化从醛、烯醇化β-二酮或β-氧代酯和β-氧代酯中一锅法合成β′-乙酰氨基-β-二羰基化合物。乙酰氯的乙腈溶液，在无溶剂条件下，室温；就β-氧代酯衍生产品而言，这些产品具有中等至优异的非对映选择性，有利于预异构体。一种预-β′-乙酰氨基-β-氧代酯的X射线晶体学分析显示了三维超分子组装体中的C-H…O和N-H…O分子间相互作用。
• ZrOCl₂•8H₂O-Catalyzed One-Pot Multicomponent Synthesis of β′-Acetamido-β-dicarbonyl Compounds with Special Reference to <i>pref</i>-Selective β′-Acetamido-β-ketoesters
  作者：Rina Ghosh、Swarupananda Maiti、Sajal K. Maity、Soumik Roy

  DOI：10.1080/00397910801997710

  日期：2008.5.23

  Abstract ZrOCl2 · 8H2O catalyzes the one-pot synthesis of β′-acetamido-β-dicarbonyl compounds in high yields from aldehyde, enolizable β-dicarbonyl compound, acetyl chloride, and acetonitrile in solvent as well as in solvent-free conditions. β′-Acetamido-β-ketoesters are formed in moderate to exclusive pref-diastereoselectivity.

  摘要 ZrOCl2 · 8H2O 在溶剂和无溶剂条件下，由醛、可烯醇化的 β-二羰基化合物、乙酰氯和乙腈以高产率催化一锅法合成 β'-乙酰氨基-β-二羰基化合物。β'-乙酰氨基-β-酮酯以中等至专有的非对映选择性形成。
• A One Pot Synthesis of β-Acetamido Ketones and Furans by Cobalt(II) Catalyzed Coupling of 1,3- or 1,4- Dicarbonyl Compounds and Aldehydes: A Remarkable Role of Dioxygen
  作者：M Reddy

  DOI：10.1016/00404-0399(50)0874c-

  日期：1995.7.3
• 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：——
• Cobalt catalyzed multiple component condensation route to β-acetamido carbonyl compound libraries
  作者：Manoj Mukhopadhyay、Beena Bhatia、Javed Iqbal

  DOI：10.1016/s0040-4039(96)02474-4

  日期：1997.2

  A simple and general procedure for the synthesis of various beta-acetamido carbonyl compounds by a cobalt catalyzed one pot multiple component condensation reaction involving ketones, aldehydes and acetonitrile is described. A library of twenty discrete beta-acetamido carbonyl compounds with two or three functional group variation was prepared. (C) 1997, Elsevier Science Ltd.