(-)-(R)-2-phenoxy-2-phenylacetic acid | 950993-21-2

• 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: (-)-(R)-2-phenoxy-2-phenylacetic acid
• 英文别名: (2R)-2-phenoxy-2-phenylacetic acid
• CAS: 950993-21-2
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: ABUKMOCUMIPDHV-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  碘苯 、 D-扁桃酸 在 copper(l) iodide 、 caesium carbonate 作用下， 以 丁腈 为溶剂， 反应 15.0h， 以17%的产率得到(-)-(R)-2-phenoxy-2-phenylacetic acid
  参考文献：
  名称：

  One-step synthesis of homochiral O-aryl and O-heteroaryl mandelic acids and their use as efficient 1H NMR chiral solvating agents

  摘要：

  Job and Buchwald's one-step copper-promoted arylation of hydroxyl groups was explored and modified so that it could be applied to the coupling of mandelic acid with several halobenzenes and haloheteroarenes. A number of new homochiral O-aryl and O-heteroaryl mandelic acids, generally presenting high enantiomeric purities, were obtained. Although yields were moderate at the best, ranging from 9% to 41%, the reaction was convenient enough to prepare new mandelic acid derivatives, some of which performed as efficient chiral solvating agents (CSAs) for the direct H-1 NMR ee value determination of several clinically and pharmacologically relevant amines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.002

文献信息

• Silver‐Catalyzed Asymmetric Insertion into Phenolic O−H Bonds using Aryl Diazoacetates and Theoretical Mechanistic Studies
  作者：Shingo Harada、Koki Tanikawa、Haruka Homma、Chigaya Sakai、Tsubasa Ito、Tetsuhiro Nemoto

  DOI：10.1002/chem.201902126

  日期：2019.9.18

  into the O-H bond of phenols was developed. A homobinuclear silver complex with a chiral phosphorous ligand was created in situ from AgNTf2 and (S)-XylylBINAP (in a 2:1 mole ratio). Detailed mechanistic studies using combined experimental and computational techniques revealed that one silver atom center of the catalyst forms a silver carbene and another one works as a Lewis acid for the nucleophilic

  已开发了由供体-受体取代的重氮化合物生成的羧甲基银对苯酚的OH键的对映选择性插入反应。由AgNTf2和（S）-XylylBINAP（以2：1的摩尔比）原位产生具有手性磷配体的同双核银络合物。使用组合的实验和计算技术进行的详细机理研究表明，催化剂的一个银原子中心形成银卡宾，而另一个作为路易斯酸用于苯酚的亲核加成。两个抗衡阴离子，两个水分子和两个银原子协同介导随后的质子化事件，从而降低活化能并控制对映选择性，从而提供了一系列有价值的α-芳基-α-芳氧基酯。
• Process for the stereoselective preparation of (-)-halofenate and derivatives thereof
  申请人：Zhu Yan

  公开号：US20070072858A1

  公开（公告）日：2007-03-29

  The present invention provides a compounds the formula (IV): and methods for producing an α-(phenoxy)phenylacetic acid compound of the formula: wherein R 1 is a member selected from the group consisting of: each R 2 is a member independently selected from the group consisting of (C 1 -C 4 )alkyl, halo, (C 1 -C 4 )haloalkyl, amino, (C 1 -C 4 )aminoalkyl, amido, (C 1 -C 4 )amidoalkyl, (C 1 -C 4 )sulfonylalkyl, (C 1 -C 4 )sulfamylalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )heteroalkyl, carboxy and nitro; the subscript n is 1 when R 1 has the formula (a) or (b) and 2 when R 1 has the formula (c) or (d); the subscript m is an integer of from 0 to 3; * indicates a carbon which is enriched in one stereoisomeric configuration; and the wavy line indicates the point of attachment of R 1 ; and compounds

  本发明提供了化合物的公式(IV)：及其制备α-(苯氧基)苯乙酸化合物的方法：其中R1是从以下组成的成员中选择的：每个R2是独立从以下组成的组中选择的成员：(C1-C4)烷基，卤素，(C1-C4)卤代烷基，氨基，(C1-C4)氨基烷基，酰胺基，(C1-C4)酰胺基烷基，(C1-C4)磺酰基烷基，(C1-C4)磺酰胺基烷基，(C1-C4)烷氧基，(C1-C4)杂烷基，羧基和硝基；当R1具有公式(a)或(b)时，下标n为1，当R1具有公式(c)或(d)时，下标n为2；下标m为0至3的整数；*表示富含一种立体异构体的碳；波浪线表示R1的连接点；和化合物
• CARBOXYLIC ACID DERIVATIVE AS AT2R RECEPTOR ANTAGONIST
  申请人：Shandong Danhong Pharmaceutical Co., Ltd.

  公开号：EP3620454B1

  公开（公告）日：2021-05-05
• US7714131B2
  申请人：——

  公开号：US7714131B2

  公开（公告）日：2010-05-11
• One-step synthesis of homochiral O-aryl and O-heteroaryl mandelic acids and their use as efficient 1H NMR chiral solvating agents
  作者：Maria Maddalena Cavalluzzi、Claudio Bruno、Giovanni Lentini、Angelo Lovece、Alessia Catalano、Alessia Carocci、Carlo Franchini

  DOI：10.1016/j.tetasy.2009.08.002

  日期：2009.9

  Job and Buchwald's one-step copper-promoted arylation of hydroxyl groups was explored and modified so that it could be applied to the coupling of mandelic acid with several halobenzenes and haloheteroarenes. A number of new homochiral O-aryl and O-heteroaryl mandelic acids, generally presenting high enantiomeric purities, were obtained. Although yields were moderate at the best, ranging from 9% to 41%, the reaction was convenient enough to prepare new mandelic acid derivatives, some of which performed as efficient chiral solvating agents (CSAs) for the direct H-1 NMR ee value determination of several clinically and pharmacologically relevant amines. (C) 2009 Elsevier Ltd. All rights reserved.