(2R)-2-[3-(phenylcarbonyl)phenyl]propanamide | 188252-75-7

• 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: (2R)-2-[3-(phenylcarbonyl)phenyl]propanamide
• 英文别名: (R)-2-(3-benzoylphenyl)propanamide；(R)-2-(3-benzoylphenyl)propionamide；Ketoprofen amide, (R)-；(2R)-2-(3-benzoylphenyl)propanamide
• CAS: 188252-75-7
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: KLWMCJJRUWWDSW-LLVKDONJSA-N

物化性质

• 沸点：
  469.3±38.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-[3-(phenylcarbonyl)phenyl]propanamide 在 三乙胺 、 三氯乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 (2R)-[3-(phenylcarbonyl)phenyl]propanenitrile
  参考文献：
  名称：

  Retention of stereochemistry in the microwave assisted synthesis of 1H-tetrazole bioisosteric moiety from chiral phenyl-acetic acid derivatives

  摘要：

  Chiral substituted phenylethyl-1H-tetrazoles were built-up from the corresponding carboxylic acid derivatives by a useful three-step synthesis. The procedure, that preserves the chiral center from racemization, was successfully applied to a selection of several hit compounds by conversion of the carboxylic acid moiety to the nitrile derivatives and subsequent reaction with trimethylstannyl azide, under microwave conditions. A useful application to the corresponding tetrazole analogue has been found also in the conversion of the aminoacidic moiety like (R)-N-Cbz-phenylglycine showing a wide potential synthetic application. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.022
• 作为产物：
  描述：

  (2R)-2-(3-苯甲酰基苯基)丙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R)-2-[3-(phenylcarbonyl)phenyl]propanamide
  参考文献：
  名称：

  Retention of stereochemistry in the microwave assisted synthesis of 1H-tetrazole bioisosteric moiety from chiral phenyl-acetic acid derivatives

  摘要：

  Chiral substituted phenylethyl-1H-tetrazoles were built-up from the corresponding carboxylic acid derivatives by a useful three-step synthesis. The procedure, that preserves the chiral center from racemization, was successfully applied to a selection of several hit compounds by conversion of the carboxylic acid moiety to the nitrile derivatives and subsequent reaction with trimethylstannyl azide, under microwave conditions. A useful application to the corresponding tetrazole analogue has been found also in the conversion of the aminoacidic moiety like (R)-N-Cbz-phenylglycine showing a wide potential synthetic application. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.022

文献信息

• Substrate Evaluation of<i>Rhodococcus erythropolis</i>SET1, a Nitrile Hydrolysing Bacterium, Demonstrating Dual Activity Strongly Dependent on Nitrile Sub-Structure
  作者：Tracey M. Coady、Lee V. Coffey、Catherine O'Reilly、Claire M. Lennon

  DOI：10.1002/ejoc.201403201

  日期：2015.2

  Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position

  红球菌 SET1 是一种新型腈水解细菌分离株，已使用 34 种腈、33 种手性和 1 种前手性进行了评估。这些底物主要由 β-羟基腈组成，在 β 位具有不同的烷基和芳基，并且在几种化合物中含有与腈不同的 α 取代基。在 α 位没有取代的 β-羟基腈的情况下，由于分离物的腈水解酶活性，酸是获得的主要产物，以及生物转化后回收的腈。出乎意料的是，当 β-羟基腈在该位置具有乙烯基时，发现酰胺是主要的水解产物。为了进一步探索这种行为，评估了在 α 位置包含吸电子基团的其他相关底物，在 SET1 存在下的生物转化过程中也观察到了酰胺。因此，这种新的分离物也证明了对似乎是底物依赖性的腈类的 NHase 活性。
• 2-Arylpropionic Acid Derivatives and Pharmaceutical Compositions Containing Them
  申请人：Allegretti Marcello

  公开号：US20080312293A1

  公开（公告）日：2008-12-18

  The present invention relates to selected (R)-2-phenyl-propionamides and (R)-2-phenyl-sulfonamides with a hydrogen bond acceptor atom/group in a well defined position in the chemical space. These compounds show a surprising potent inhibitory effect on C5a induced human PMN chemotaxis. The compounds of the invention absolutely lack of CXCL8 inhibitory activity. Said compounds are useful in the treatment of pathologies depending on the chemotactic activation of neutrophils and monocytes induced by the fraction C5a of the complement. In particular, the compounds of the invention are useful in the treatment of sepsis, psoriasis, rheumatoid arthritis, ulcerative colitis, acute respiratory distress syndrome, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of injury caused by ischemia and reperfusion.

  本发明涉及在化学空间中具有氢键受体原子/基团的选定（R）-2-苯基-丙酰胺和（R）-2-苯基-磺酰胺。这些化合物表现出惊人的强烈抑制C5a诱导的人类PMN趋化性的效果。本发明的化合物绝对缺乏CXCL8抑制活性。所述化合物在治疗与补体C5a诱导的中性粒细胞和单核细胞趋化活化有关的病理过程中有用。特别是，在治疗败血症、牛皮癣、类风湿性关节炎、溃疡性结肠炎、急性呼吸窘迫综合征、特发性纤维化、肾小球肾炎以及缺血再灌注损伤的预防和治疗方面，本发明的化合物非常有用。
• 2-ARYLPROPIONIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：DOMPE' pha.r.ma S.p.A.

  公开号：EP1856031B1

  公开（公告）日：2009-02-25
• US7939521B2
  申请人：——

  公开号：US7939521B2

  公开（公告）日：2011-05-10
• Retention of stereochemistry in the microwave assisted synthesis of 1H-tetrazole bioisosteric moiety from chiral phenyl-acetic acid derivatives
  作者：Mara Tomassetti、Michela Fanì、Gianluca Bianchini、Sandra Giuli、Andrea Aramini、Sandro Colagioia、Giuseppe Nano、Samuele Lillini

  DOI：10.1016/j.tetlet.2013.09.022

  日期：2013.11

  Chiral substituted phenylethyl-1H-tetrazoles were built-up from the corresponding carboxylic acid derivatives by a useful three-step synthesis. The procedure, that preserves the chiral center from racemization, was successfully applied to a selection of several hit compounds by conversion of the carboxylic acid moiety to the nitrile derivatives and subsequent reaction with trimethylstannyl azide, under microwave conditions. A useful application to the corresponding tetrazole analogue has been found also in the conversion of the aminoacidic moiety like (R)-N-Cbz-phenylglycine showing a wide potential synthetic application. (C) 2013 Elsevier Ltd. All rights reserved.