N-(2-oxo-2-(thiophen-2-yl)ethyl)acetamide | 6660-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-oxo-2-(thiophen-2-yl)ethyl)acetamide
• 英文别名: Acetamidoacetylthiophene；N-(2-oxo-2-thiophen-2-ylethyl)acetamide
• CAS: 6660-07-7
• 化学式: C₈H₉NO₂S
• 分子量: 183.231
• InChiKey: TYDRYAXSQDKHEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-oxo-2-(thiophen-2-yl)ethyl)acetamide 在 硫酸 作用下， 反应 1.5h， 以64%的产率得到2-methyl-5-(thiophen-2-yl)-1,3-oxazole
  参考文献：
  名称：

  Probing the ‘bipolar’ nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms

  摘要：

  A series of potent inhibitors of human carbonic anhydrase (CA) isoforms I and II has been prepared via a direct, chemoselective sulfochlorination of a range of 1,3-oxazolyl benzenes and thiophenes, followed by primary sulfonamide synthesis. The latter functionality is a known zinc-binding group (ZBG) responsible for anchoring the inhibitors to the CA's zinc metal ion. The compound's periphery as well as the overall scaffold geometry was designed to enable optimal interactions with the two distinct sides of the enzyme's active site, one of which is lined with hydrophobic residues and while the other is predominantly hydrophilic. As a result, several compounds inhibiting the therapeutically important cytosolic CA I and CA II in picomolar range have been identified. These compounds are one of the most potent CA inhibitors identified to-date. Not only the remarkable (>10 000-fold), cytosolic CA I and CA II selectivity vs. the membrane-bound CA IX and CA XII isoforms, but also the pronounced CA II/I selectivity observed in some cases, allow considering this series as a set of isoform-selective chemical biology tools and promising starting points for drug candidate development. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.022
• 作为产物：
  描述：

  2-溴-1-(2-THIENYL)-1-ETHANONE 在 吡啶 、 乌洛托品 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 N-(2-oxo-2-(thiophen-2-yl)ethyl)acetamide
  参考文献：
  名称：

  Probing the ‘bipolar’ nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms

  摘要：

  A series of potent inhibitors of human carbonic anhydrase (CA) isoforms I and II has been prepared via a direct, chemoselective sulfochlorination of a range of 1,3-oxazolyl benzenes and thiophenes, followed by primary sulfonamide synthesis. The latter functionality is a known zinc-binding group (ZBG) responsible for anchoring the inhibitors to the CA's zinc metal ion. The compound's periphery as well as the overall scaffold geometry was designed to enable optimal interactions with the two distinct sides of the enzyme's active site, one of which is lined with hydrophobic residues and while the other is predominantly hydrophilic. As a result, several compounds inhibiting the therapeutically important cytosolic CA I and CA II in picomolar range have been identified. These compounds are one of the most potent CA inhibitors identified to-date. Not only the remarkable (>10 000-fold), cytosolic CA I and CA II selectivity vs. the membrane-bound CA IX and CA XII isoforms, but also the pronounced CA II/I selectivity observed in some cases, allow considering this series as a set of isoform-selective chemical biology tools and promising starting points for drug candidate development. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.022

文献信息

• Potassium-Base-Mediated Autoxidative Diastereoselective Homocoupling of <i>N</i>-Acyl-2-aminoacetophenones
  作者：Yingwei Wang、Mingrong Yang、Chichou Lao、Zhihong Jiang

  DOI：10.1021/acs.orglett.2c00618

  日期：2022.4.15

  general and highly efficient method for the synthesis of dl-2,3-diamide-1,4-diones via autoxidative dehydrogenative homocoupling of N-acyl-2-aminoacetophenones mediated by t-BuOK. The transformation is mild, operationally simple, and environmentally friendly. Control experiments and stereochemical results suggest that the substrate undergoes autoxidation followed by a diastereoselective SN2 reactopm.

  我们在此报告了一种通用且高效的方法，用于通过由t -BuOK 介导的N-酰基-2-氨基苯乙酮的自氧化脱氢同源偶联来合成dl -2,3-diamide-1,4- diones。改造温和、操作简单、环保。对照实验和立体化学结果表明，底物发生自氧化，然后发生非对映选择性 S N 2 反应。
• Oxidative Cross-Coupling of α-Amino Ketones with Alcohols Enabled by I₂-Catalyzed C–H Hydroxylation
  作者：Yingwei Wang、Mingrong Yang、Chichou Lao、Hanxuan Wang、Zhihong Jiang

  DOI：10.1021/acs.joc.3c01469

  日期：2023.10.20

  oxidative cross-coupling of α-amino ketones with a wide range of alcohols is described. Using a combination of air and dimethyl sulfoxide (DMSO) as oxidants, the protocol allows an efficient synthesis of α-carbonyl N,O-acetals with high functional group tolerance and enables the late-stage introduction of α-amino ketones into biorelevant alcohols. Moreover, the present method can be used in the coupling of

  描述了α-氨基酮与多种醇的I 2催化氧化交叉偶联。该方案使用空气和二甲基亚砜（DMSO）的组合作为氧化剂，可以有效合成具有高官能团耐受性的α-羰基N,O-缩醛，并能够在后期将α-氨基酮引入生物相关醇中。此外，该方法可用于α-氨基酮与其他种类的亲核试剂的偶联，这对于α-氨基酮的官能化具有很大的通用性。初步的机理研究表明，α-氨基酮的 C-H 羟基化已被认为是随后脱水偶联的关键步骤。
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