N-(2-acetyl-3-oxo-1-phenylbutyl)acetamide | 195969-43-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-acetyl-3-oxo-1-phenylbutyl)acetamide
• CAS: 195969-43-8
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: IOXVORSURGWLGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 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：
  63.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-acetyl-3-oxo-1-phenylbutyl)acetamide 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以66%的产率得到N-[(3,5-dimethyl-1H-pyrazol-4-yl)(phenyl)methyl]acetamide
  参考文献：
  名称：

  N-(α-Amidoalkyl)benzotriazole-mediated synthesis of β′-amido β-diketones: a general synthetic protocol for N-[β-(3,5-di and 1,3,5-trisubstituted pyrazol-4-yl)alkyl] amides

  摘要：

  Various beta '-amido-beta-diketones were first synthesized with N-(alpha-amidoalkyl)benzotriazole-mediated amidoalkylation of 1,3-diketones in moderate yields. These intermediates undergo rapid condensation with hydrazines to give the corresponding N-[beta-(3,5-di and 1,3,5-trisubstituted pyrazol-4-yl)alkyl]amides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.047
• 作为产物：
  描述：

  N-(1-benzotriazoyl-1-phenylmethyl)acetamide 、 乙酰丙酮 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.67h， 以89%的产率得到N-(2-acetyl-3-oxo-1-phenylbutyl)acetamide
  参考文献：
  名称：

  N-(α-Amidoalkyl)benzotriazole-mediated synthesis of β′-amido β-diketones: a general synthetic protocol for N-[β-(3,5-di and 1,3,5-trisubstituted pyrazol-4-yl)alkyl] amides

  摘要：

  Various beta '-amido-beta-diketones were first synthesized with N-(alpha-amidoalkyl)benzotriazole-mediated amidoalkylation of 1,3-diketones in moderate yields. These intermediates undergo rapid condensation with hydrazines to give the corresponding N-[beta-(3,5-di and 1,3,5-trisubstituted pyrazol-4-yl)alkyl]amides. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.10.047

文献信息

• Facile and diastereoselective synthesis of β-acetamido ketones and keto esters via direct Mannich-type reaction
  作者：Hui Mao、Jieping Wan、Yuanjiang Pan

  DOI：10.1016/j.tet.2008.11.071

  日期：2009.1

  A Mannich-type three-component reaction involving aldehydes, acetamide, and enolizable ketones or β-keto esters for the preparation of β-acetamido carbonyl compounds in the presence of TMSCl is described. This newly developed protocol is operationally convenient, widely applicable, and highly diastereoselective.

  描述了用于在TMCSC1存在下制备β-乙酰氨基羰基化合物的涉及醛，乙酰胺和可烯醇化的酮或β-酮酯的曼尼希型三组分反应。该新开发的协议操作方便，适用范围广且具有非对映选择性。
• Mannich Curcuminoids as Potent Anticancer Agents
  作者：Márió Gyuris、László Hackler、Lajos I. Nagy、Róbert Alföldi、Eszter Rédei、Annamária Marton、Tibor Vellai、Nóra Faragó、Béla Ózsvári、Anasztázia Hetényi、Gábor K. Tóth、Péter Sipos、Iván Kanizsai、László G. Puskás

  DOI：10.1002/ardp.201700005

  日期：2017.7

  A series of novel curcuminoids were synthesised for the first time via a Mannich‐3CR/organocatalysed Claisen–Schmidt condensation sequence. Structure–activity relationship (SAR) studies were performed by applying viability assays and holographic microscopic imaging to these curcumin analogues for anti‐proliferative activity against A549 and H1975 lung adenocarcinoma cells. The TNFα‐induced NF‐κB inhibition

  通过 Mannich-3CR/有机催化的 Claisen-Schmidt 缩合序列，首次合成了一系列新型姜黄素。通过对这些姜黄素类似物应用活力测定和全息显微成像，对 A549 和 H1975 肺腺癌细胞具有抗增殖活性，进行构效关系 (SAR) 研究。TNFα 诱导的 NF-κB 抑制和自噬诱导作用与类似物的细胞毒性潜力密切相关。当在 A549 异种移植模型中以最大耐受剂量的六分之一将最有效的类似物 44 添加到脂质体中时，观察到对肿瘤生长的显着抑制。这些曼尼希姜黄素的新活性谱需要进一步的临床前研究。
• 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。
• A Modified and Green Procedure for the Synthesis of<i>β</i>-Amido Ketones Using a Br?nsted-Acidic Ionic Liquid as Novel and Reusable Catalyst
  作者：Abolghasem Davoodnia、Majid M. Heravi、Leila Rezaei-Daghigh、Niloofar Tavakoli-Hoseini

  DOI：10.1002/cjoc.201090091

  日期：2010.1

  and improved method for the synthesis of β‐amido ketones through one‐pot multi‐component reaction of an enolizable ketone, aryl aldehyde, acetonitrile or benzonitrile in the presence of trimethylsilyl chloride using 3‐methyl‐1‐(4‐sulfonic acid)butylimidazolium hydrogen sulfate [(CH2)4SO3HMIM][HSO4], a Br?nsted‐acidic ionic liquid, as an effective and recyclable catalyst is described. The present methodology

  在三甲基氯硅烷存在下，使用3-甲基-1-（4-磺酸）在三甲基甲硅烷基氯的存在下，通过可烯化的酮，芳基醛，乙腈或苄腈的单锅多组分反应，合成绿色改进的β-酰胺基酮的方法介绍了一种布朗斯台德酸性离子液体，即有效的可回收催化剂）-丁基咪唑硫酸氢盐[（CH 2）4 SO 3 HMIM] [HSO 4 ]。本方法具有许多优点，例如操作简单，易于操作，相对较短的反应时间以及良好的收率。
• [EN] NOVEL MEDICINAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS MÉDICAUX
  申请人：AVIDIN KUTATO FEJLESZTOE ES KERESKEDELMI KORLATOLT

  公开号：WO2013041895A1

  公开（公告）日：2013-03-28

  The invention relates to novel compounds of general formula (I), and their preparation, pharmaceutical preparations containing compounds of general formula (I), and the use of these compounds in therapeutic procedures. The invention also relates to compounds of general formula (VI), which can be used as intermediates in the processes for the preparation of compounds of general formula (I).

  该发明涉及一般式（I）的新化合物，以及它们的制备、含有一般式（I）化合物的药物制剂，以及这些化合物在治疗程序中的使用。该发明还涉及一般式（VI）的化合物，可用作制备一般式（I）化合物的过程中的中间体。