N-(1,1-二甲基-2-氧代-2-苯基乙基)-苯甲酰胺 | 56965-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-(1,1-二甲基-2-氧代-2-苯基乙基)-苯甲酰胺
• 英文名称: N-(2-methyl-1-oxo-1-phenylpropan-2-yl)benzamide
• 英文别名: 2-benzoylamino-2-methyl-1-phenyl-1-propanone；N-(1,1-dimethyl-2-oxo-2-phenyl-ethyl)-benzamide；N-(1,1-Dimethyl-2-oxo-2-phenyl-aethyl)-benzamid；α-Benzamino-isobutyrophenon；N-(1,1-Dimethyl-2-oxo-2-phenyl-ethyl)-benzamide
• CAS: 56965-16-3
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: PZQPMVQLTCLXNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 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-(1,1-二甲基-2-氧代-2-苯基乙基)-苯甲酰胺 在 sodium sulfide 、 二乙胺基三氟化硫 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.17h， 生成 N-(2-methyl-1-oxo-1-phenylpropan-2-yl)benzothioamide
  参考文献：
  名称：

  DAST-Mediated Cyclization of α,α-Disubstituted-α-acylaminoketones: Efficient and Divergent Synthesis of Unprecedented Heterocycles

  摘要：

  The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of alpha,alpha-disubstituted-alpha-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substituted by a range of nucleophiles to provide in high yields a diverse array of unprecedented heterocyclic frameworks.

  DOI：

  10.1021/ol102454e
• 作为产物：
  描述：

  5-fluoro-4,4-dimethyl-2,5-diphenyl-4,5-dihydrooxazole 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-(1,1-二甲基-2-氧代-2-苯基乙基)-苯甲酰胺
  参考文献：
  名称：

  DAST-Mediated Cyclization of α,α-Disubstituted-α-acylaminoketones: Efficient and Divergent Synthesis of Unprecedented Heterocycles

  摘要：

  The design of a new potent nonsteroidal ecdysone agonist led to the discovery of a diethylaminosulfur trifluoride (DAST)-mediated cyclization of alpha,alpha-disubstituted-alpha-acylaminoketones. The resulting fluorooxazolines can be ring-opened or selectively substituted by a range of nucleophiles to provide in high yields a diverse array of unprecedented heterocyclic frameworks.

  DOI：

  10.1021/ol102454e

文献信息

• Solid phase synthesis of α-acylamino-α,α-disubstituted ketones
  作者：Colin M. Tice、Enrique L. Michelotti、Ernesto G. Mata、Ernesto Nicolàs、Javier Garcia、Fernando Albericio

  DOI：10.1016/s0040-4039(02)01803-8

  日期：2002.10

  α-Acylamino-α,α-disubstituted ketones are of interest as ecdysone agonists. Solid phase synthesis of prototypical α-acylamino-α,α-disubstituted ketones on two different solid supports is described. In both cases the ketone was formed by reaction of a Grignard reagent with an N-acyl-α,α-disubstituted amino acid immobilized through its carboxylate as a Weinreb amide derivative.

  α-酰基氨基-α，α-二取代的酮作为蜕皮激素激动剂是令人感兴趣的。描述了在两种不同的固体载体上的原型α-酰基氨基-α，α-二取代酮的固相合成。在这两种情况下，酮都是通过格氏试剂与通过其羧酸盐固定为Weinreb酰胺衍生物的N-酰基-α，α-二取代氨基酸反应形成的。
• Alpha-acylaminoketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
  申请人：Intrexon Corporation

  公开号：EP2392561A1

  公开（公告）日：2011-12-07

  This invention relates to a method to modulate exogenous gene expression in which an ecdysone receptor complex comprising: a DNA binding domain; a ligand binding domain; a transactivation domain; and a ligand is contacted with a DNA construct comprising: the exogenous gene and a response element; wherein the exogenous gene is under the control of the response element and binding of the DNA binding domain to the response element in the presence of the ligand results in activation or suppression of the gene. The ligands comprise a class of ketones.

  本发明涉及一种调节外源基因表达的方法，其中包括 DNA 结合结构域、配体结合结构域、转录激活结构域和配体的蜕皮激素受体复合物与包括外源基因和反应元件的 DNA 构建体接触；其中外源基因受反应元件控制，DNA 结合结构域在配体存在的情况下与反应元件结合导致基因的激活或抑制。配体包括一类酮。
• Synthesis and SAR of α-Acylaminoketone ligands for control of gene expression
  作者：Colin M Tice、Robert E Hormann、Christine S Thompson、Jennifer L Friz、Caitlin K Cavanaugh、Enrique L Michelotti、Javier Garcia、Ernesto Nicolas、Fernando Albericio

  DOI：10.1016/s0960-894x(02)00980-0

  日期：2003.2

  A lead discovery library and a follow-up focused library of alpha-acylaminoketones were designed based on known dibenzoylhydrazine ecdysone agonists, including GS(TM)-E. The compounds were assayed in mammalian cells expressing the ecdysone receptor from Bombyx mori for their ability to cause expression of a reporter gene downstream of an ecdysone response element. The most potent alpha-acylaminoketones were comparable to GS(TM)-E in this assay. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Reactions of azirines with sulfur nucleophiles. 4. Treatment of 2H-azirine with mercaptosubstituted acids. reactions of aziridinyl alkyl sulfides with carboxylic acids and acyl chloride derivatives
  作者：R. S. �l'kinson、A. V. Eremeev

  DOI：10.1007/bf00519936

  日期：1986.2
• Bachstez, Chemische Berichte, 1914, vol. 47, p. 3166
  作者：Bachstez

  DOI：——

  日期：——