2-(3-Methylphenyl)butanoyl chloride | 51631-47-1

• 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-(3-Methylphenyl)butanoyl chloride
• 英文别名: 2-(3-methylphenyl)butanoyl chloride
• CAS: 51631-47-1
• 化学式: C₁₁H₁₃ClO
• 分子量: 196.677
• InChiKey: RZOZVUWAOJOCQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-Methylphenyl)butanoyl chloride 在 三乙胺 作用下， 以 乙醚 为溶剂， 以790 mg的产率得到m-tolyl ethyl ketene
  参考文献：
  名称：

  路易斯酸催化双环[1.1.0]丁烷与乙烯酮的缩甲醛(3+2)-环加成反应

  摘要：

  提出了一种温和、高效且无过渡金属的方法，通过路易斯酸催化容易获得的双环[1.1.0]丁烷和乙烯酮的形式(3+2)-环加成来制备有价值的双环[2.1.1]己烷。双环[2.1.1]己烷核心3位上的官能团具有优异的耐受性和多种取代模式。

  DOI：

  10.1002/anie.202304771
• 作为产物：
  描述：

  2-(m-tolyl)butanoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(3-Methylphenyl)butanoyl chloride
  参考文献：
  名称：

  路易斯酸催化双环[1.1.0]丁烷与乙烯酮的缩甲醛(3+2)-环加成反应

  摘要：

  提出了一种温和、高效且无过渡金属的方法，通过路易斯酸催化容易获得的双环[1.1.0]丁烷和乙烯酮的形式(3+2)-环加成来制备有价值的双环[2.1.1]己烷。双环[2.1.1]己烷核心3位上的官能团具有优异的耐受性和多种取代模式。

  DOI：

  10.1002/anie.202304771

文献信息

• Addition–Rearrangement of Ketenes with Lithium<i>N</i>-<i>tert</i>-Butanesulfinamides: Enantioselective Synthesis of α,α-Disubstituted α-Hydroxycarboxylic Acid Derivatives
  作者：Peng-Ju Ma、Fan Tang、Yun Yao、Chong-Dao Lu

  DOI：10.1021/acs.orglett.9b01555

  日期：2019.6.21

  Addition of the lithium salts of chiral N-substituted tert-butanesulfinamides to ketenes and subsequent silylation initiates stereoselective [2,3]-rearrangement, which affords enantioenriched α,α-disubstituted α-sulfenyloxy carboxamides through a reaction that faithfully transfers the absolute stereochemistry of the lithiated sulfinylamides to the α-carbon of the amide products. This addition–rearrangement

  将手性N-取代叔丁亚磺酰胺的锂盐加到乙烯酮中，随后进行甲硅烷基化反应，引发立体选择性[2,3]-重排，该反应可通过忠实地转移绝对立体化学的反应得到对映体富集的α，α-二取代的α-亚磺酰氧基羧酰胺。将锂化的亚磺酰胺转化为酰胺产物的α-碳。这种加成-重排可以与在单个烧瓶中由酰氯形成乙烯酮一起进行，从而提供了一种新的实用的合成α-羟基羧酸衍生物的途径。
• Dochnahl, Maximilian; Fu, Gregory C., Angewandte Chemie - International Edition, 2009, vol. 48, p. 2391 - 2393
  作者：Dochnahl, Maximilian、Fu, Gregory C.

  DOI：——

  日期：——
• Competitive Activity-Based Protein Profiling Identifies Aza-β-Lactams as a Versatile Chemotype for Serine Hydrolase Inhibition
  作者：Andrea M. Zuhl、Justin T. Mohr、Daniel A. Bachovchin、Sherry Niessen、Ku-Lung Hsu、Jacob M. Berlin、Maximilian Dochnahl、María P. López-Alberca、Gregory C. Fu、Benjamin F. Cravatt

  DOI：10.1021/ja300799t

  日期：2012.3.21

  Serine hydrolases are one of the largest and most diverse enzyme classes in Nature. Most serine hydrolases lack selective inhibitors, which are valuable probes for assigning functions to these enzymes. We recently discovered a set of aza-beta-lactams (ABLs) that act as potent and selective inhibitors of the mammalian serine hydrolase protein-phosphatase methylesterase-1 (PME-1). The ABLs inactivate PME-1 by covalent acylation of the enzyme's serine nucleophile, suggesting that they could offer a general scaffold for serine hydrolase inhibitor discovery. Here, we have tested this hypothesis by screening ABLs more broadly against cell and tissue proteomes by competitive activity-based protein profiling (ABPP), leading to the discovery of lead inhibitors for several serine hydrolases, including the uncharacterized enzyme alpha,beta-hydrolase domain-containing 10 (ABHD10). ABPP-guided medicinal chemistry yielded a compound ABL303 that potently (IC50 approximate to 30 nM) and selectively inactivated ABHD10 in vitro and in living cells. A comparison of optimized inhibitors for PME-1 and ABHD10 indicates that modest structural changes that alter steric bulk can tailor the ABL to selectively react with distinct, distantly related serine hydrolases. Our findings, taken together, designate the ABL as a versatile reactive group for creating first-in-class serine hydrolase inhibitors.
• [EN] AlphaZetaAlpha-beta-LACTAM COMPOUNDS AND METHODS OF USING<br/>[FR] COMPOSÉS AZA-Beta-LACTAMES ET PROCÉDÉS D'UTILISATION
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2013152272A1

  公开（公告）日：2013-10-10

  The invention is directed to methods of modulation of serine hydrolase ABHD10, which can be selective with respect to other serine hydrolases such as PME-1. The compounds of the invention, or compounds useful in practice of a method of the invention, are aza-β-lactams, of which the (R)-enantiomer is preferred, for modulation of ABHD10. Methods of preparation are provided comprising the cycloaddition of dialkylazodicarboxylates with ketenes using the catalyst PPY*. The invention provides methods of treatment of conditions in patients for which modulation of ABHD10 is indicated, including pain, inflammation, metabolic disorders, solid tumors, or obesity.
• Lewis Acid Catalyzed Formal (3+2)‐Cycloaddition of Bicyclo[1.1.0]butanes with Ketenes
  作者：Niklas Radhoff、Constantin G. Daniliuc、Armido Studer

  DOI：10.1002/anie.202304771

  日期：2023.8.21

  efficient and transition-metal-free method for the preparation of valuable bicyclo[2.1.1]hexanes by Lewis acid catalyzed formal (3+2)-cycloaddition of readily available bicyclo[1.1.0]butanes and ketenes is presented. Excellent tolerance towards functional groups and versatile substitution patterns in the 3-position of the bicyclo[2.1.1]hexane core are demonstrated.

  提出了一种温和、高效且无过渡金属的方法，通过路易斯酸催化容易获得的双环[1.1.0]丁烷和乙烯酮的形式(3+2)-环加成来制备有价值的双环[2.1.1]己烷。双环[2.1.1]己烷核心3位上的官能团具有优异的耐受性和多种取代模式。