2-[2-(2-oxo-2-phenylethyl)phenyl]acetic acid | 72686-12-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[2-(2-oxo-2-phenylethyl)phenyl]acetic acid
• 英文别名: 2-(2-Phenacylphenyl)acetic acid；2-(2-phenacylphenyl)acetic acid
• CAS: 72686-12-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: AVZOHHXDYUKKKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-(2-oxo-2-phenylethyl)phenyl]acetic acid 在 ammonium acetate 、 四丁基碘化铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 20.0~120.0 ℃ 、500.01 kPa 条件下， 反应 5.0h， 生成 3-benzyl-4-phenyl-1,3-dihydro-3-benzoazepin-2-one
  参考文献：
  名称：

  Microwave assisted synthesis of 3-benzazepin-2-ones as building blocks for 2,3-disubstituted tetrahydro-3-benzazepines

  摘要：

  Microwave assisted condensation of primary amines with keto acids 1a-c provided directly 3,4-disubstituted 1,3-dihydro-3-benzazepin-2-ones 2. Whereas small amine size, such as NH3 afforded high yields of secondary lactams 2a, 2d, and 2g, primary amines with larger substituents in alpha-position led to lower yields of 2 or even to regioisomeric indanone derivatives 4. However, subsequent alkylation of 2a, 2d, and 2g with various alkyl halides provided the corresponding N-substituted 3-benzazepin-2-ones 2 in good yields. Hydrogenation of 2 followed by BH3 reduction led to 3-benzazepines 9. 3-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (9c) reveals high sigma(1) affinity and selectivity over sigma(2) and NMDA receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.052
• 作为产物：
  描述：

  1,2-苯二乙酸 、 苯基锂 以 四氢呋喃 、 二丁醚 为溶剂， 反应 24.0h， 以35%的产率得到2-[2-(2-oxo-2-phenylethyl)phenyl]acetic acid
  参考文献：
  名称：

  Synthesis of Phenylacetic Acids with 2-Oxoalkyl Substituents in theortho-Position fromo-Phenylenediacetic Acid

  摘要：

  本文介绍了一步合成 2-(2-氧代烷基)取代的苯乙酸的方法。将有机锂化合物非常缓慢地加入邻苯二乙酸是以高产率获得所需的δ-氧代酸的关键特征。在半金属阴离子形成的基础上，解释了从二元酸中选择性形成牺 牲-氧代酸的原因。

  DOI：

  10.1055/s-2008-1067201

文献信息

• Asymmetric Synthesis of Enantiomerically Pure 2-Substituted Tetrahydro-3-benzazepines and Their Affinity to σ₁ Receptors
  作者：Syed Masood Husain、Roland Fröhlich、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1021/jo900087e

  日期：2009.4.3

  pairs of enantiomerically pure 2-substituted tetrahydro-3-benzazepines 12a−d and ent-12a−d, which were tested for their σ1, σ2, and NMDA receptor affinities. The 2-butyl and the 2-phenyl derivatives 12c and 12d show very high σ1 affinity with Ki values of 16 and 50 nM, respectively. The eudismic ratios are greater than 50, reflecting highly stereoselective interaction with the σ1 receptor. Both σ1

  描述了对映体纯的2-取代的四氢-3-苯并ze庚因的非常短的不对称合成。首先，合成3-苯基-2,3,11,11a-四氢[1,3]恶唑并[2,3- b ] [3]苯并ze庚因-5（6 H）-酮3a - d和4a - d。的缩合2-（2-氧代）苯基乙酸1A - d与（[R）-phenylglycinol（2）。除11a-苯基衍生物3d / 4d（比例为91：9）外，非对映体11a-烷基衍生物3a - c / 4a - c的比例差不多是50:50。通过NOE实验以及X射线晶体结构分析证明了在11a位新形成的手性中心的构型。恶唑并[2,3-的减少b ] [3]苯并吖庚因5（6 ħ） -酮的反式- 3和顺式- 4与的AlCl 3 /的LiAlH 4（1：3）发生了与配置的保留，并且得到2,3-二取代的四氢-3-苯并ze庚因10和11。在最后一步中，从10和11中除去N-（2-羟基-1-苯乙基）残基通过
• Asymmetric synthesis and σ receptor affinity of enantiomerically pure 1,4-disubstituted tetrahydro-1H-3-benzazepines
  作者：Syed Masood Husain、Marie Theres Heim、Dirk Schepmann、Bernhard Wünsch

  DOI：10.1016/j.tetasy.2009.05.017

  日期：2009.7

  A very short (three steps) asymmetric synthesis of enantiomerically pure 1,4-disubstituted tetrahydro-1H-3-benzazepines 14 has been elaborated upon, starting from the trans- and cis-configured 11a-substituted 3-phenyl-2,3,11,11a-tetrahydro[1,3]oxazolo[2,3-b]-[3]-benzazepin-5(6H)-ones 6 and 7. The stereoisomerically pure lactams 6 and 7 were benzylated to give 6-benzyl-substituted products 8 and 9.

  非常短的（三步）不对称对映体纯的1,4-二取代四氢-1的合成ħ -3-苯并吖庚因14已被详细阐述，从起始的反式-和顺-型11a的取代的3-苯基-2,3- ，11，11a-四氢[1，3]恶唑并[2，3- b ]-[3] -苯并ze庚因-5（6 H）-一个6和7。将立体异构纯的内酰胺6和7苄基化，得到6-苄基取代的产物8和9。NOE实验显示反苄基残基和11a-位残基的-构型表明苄基化反应的立体化学受11a-位的立体中心控制。用AlCl 3 / LiAlH 4（1/3）还原苄基化的三环苯并内酰胺8和9，得到1,3,4-三取代的3-苯并pine庚因12和13，它们立体选择性地形成并保留构型。最后，通过氢解裂解去除N-（2-羟基-1-苯乙基）残基，形成对映体纯的1,4-二取代的3-苯并ze庚因14。的σ 1，σ 2对映体纯3-苯并ze庚因14和ent - 14的NMDA受体亲和力已在竞争性受体结合研究中进行了研究。丁基衍生物ENT
• Synthesis of Phenylacetic Acids with 2-Oxoalkyl Substituents in the<i>ortho</i>-Position from<i>o</i>-Phenylenediacetic Acid
  作者：Bernhard Wünsch、Syed Husain

  DOI：10.1055/s-2008-1067201

  日期：2008.9

  A one-step procedure for the synthesis of 2-(2-oxoalkyl)-substituted phenylacetic acids is described. Very slow addition of organolithium compounds to o-phenylenediacetic acid is the crucial feature to obtain the desired ε-oxo acids in good yields. The selective formation of the ε-oxo acids from the diacid is explained on the basis of hemiketal anion formation.

  本文介绍了一步合成 2-(2-氧代烷基)取代的苯乙酸的方法。将有机锂化合物非常缓慢地加入邻苯二乙酸是以高产率获得所需的δ-氧代酸的关键特征。在半金属阴离子形成的基础上，解释了从二元酸中选择性形成牺 牲-氧代酸的原因。
• Microwave assisted synthesis of 3-benzazepin-2-ones as building blocks for 2,3-disubstituted tetrahydro-3-benzazepines
  作者：Soumya Sarkar、Syed Masood Husain、Dirk Schepmann、Roland Fröhlich、Bernhard Wünsch

  DOI：10.1016/j.tet.2012.01.052

  日期：2012.3

  Microwave assisted condensation of primary amines with keto acids 1a-c provided directly 3,4-disubstituted 1,3-dihydro-3-benzazepin-2-ones 2. Whereas small amine size, such as NH3 afforded high yields of secondary lactams 2a, 2d, and 2g, primary amines with larger substituents in alpha-position led to lower yields of 2 or even to regioisomeric indanone derivatives 4. However, subsequent alkylation of 2a, 2d, and 2g with various alkyl halides provided the corresponding N-substituted 3-benzazepin-2-ones 2 in good yields. Hydrogenation of 2 followed by BH3 reduction led to 3-benzazepines 9. 3-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (9c) reveals high sigma(1) affinity and selectivity over sigma(2) and NMDA receptors. (C) 2012 Elsevier Ltd. All rights reserved.