(2S)-2-benzamido-2-(4-hydroxyphenyl)acetic acid | 47074-71-5

• 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: (2S)-2-benzamido-2-(4-hydroxyphenyl)acetic acid
• CAS: 47074-71-5
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: AFBMJKAJPZXKPS-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 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：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S)-2-benzamido-2-(4-hydroxyphenyl)acetic acid 在 乙酰氯 作用下， 生成 N-benzoyl-(4-OH)-L-phenylglycine methyl ester
  参考文献：
  名称：

  Genotoxic activity of halogenated phenylglycine derivatives

  摘要：

  The discovery of genotoxic amino acids derived from phenylglycine, and possessing halogen substituents, is described. The utility of hypervalent iodine reagents in the synthesis of this class of compounds is highlighted. The mechanism of action of the (haloaryl)glycines was studied in Saccharomyces cerevisiae.

  DOI：

  10.1016/j.bmcl.2006.08.111
• 作为产物：
  描述：

  4-p-Hydroxybenzyl-2-phenyloxazolin-5-on 以 水 为溶剂， 反应 120.0h， 生成 (R)-N-benzoyl-4-hydroxyphenylglycine 、 (2S)-2-benzamido-2-(4-hydroxyphenyl)acetic acid
  参考文献：
  名称：

  化学酶促氨基酸的不对称合成。对映选择性水解2-苯基-恶唑啉-5-酮。

  摘要：

  猪胰脂肪酶和黑曲霉的脂肪酶催化一系列4-取代的-2-苯基-恶唑啉-5-酮的对映选择性水解，分别产生光学活性的（）-和（）-N-苯甲酰基氨基酸。

  DOI：

  10.1016/0040-4039(92)88111-h

文献信息

• Pheny (alkyl)carboxylic acid derivatives and dionic phenylalkylheterocyclic derivatives and their use as medicines with serum glucose and/or serum lipid lowering activity
  申请人：Giannessi Fabio

  公开号：US20050032787A1

  公开（公告）日：2005-02-10

  Formula (I) compounds are described: Where the groups are as defined here below, and their use as medinies, particularly as serum glucose and serum lipid lowering agents. Said medicines are useful for the prophylaxis and treatment of diabetes, particularly type 2, and its complications, Syndrome X, the various forms of insulin resistance, and hyperlipidaemias, and present reduced side effects, and, particularly, reduced or no liver toxicity.

  描述了公式(I)化合物：其中各组如下所定义，并且它们的用途作为药物，特别是作为血清葡萄糖和血清脂质降低剂。所述药物对于预防和治疗糖尿病，特别是2型糖尿病及其并发症，综合征X，各种形式的胰岛素抵抗和高脂血症非常有用，并且具有减少的副作用，特别是减少或无肝毒性。
• PHENY(ALKYL)CARBOXYLIC ACID DERIVATIVES AND DIONIC PHENYLALKYLHETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDICINES WITH SERUM GLUCOSE AND/OR SERUM LIPID LOWERING ACTIVITY
  申请人：SIGMA-TAU IndustrieFarmaceutiche Riunite S.p.A.

  公开号：EP1465858A2

  公开（公告）日：2004-10-13
• [EN] PHENY(ALKYL)CARBOXYLIC ACID DERIVATIVES AND DIONIC PHENYLALKYLHETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDICINES WITH SERUM GLUCOSE AND/OR SERUM LIPID LOWERING ACTIVITY<br/>[FR] DERIVES D'ACIDE PHENY(ALKYL)CARBOXYLIQUE ET DERIVES PHENYLALKYLHETEROCYCLIQUES DIONIQUES ET LEUR UTILISATION COMME MEDICAMENTS A ACTIVITE D'ABAISSEMENT DE NIVEAU DE GLUCOSE SERIQUE ET/OU LIPIDES SERIQUES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2003059864A2

  公开（公告）日：2003-07-24

  Formula (I) compounds are described: Where the groups are as defined here below, and their use as medinies, particularly as serum glucose and serum lipid lowering agents. Said medicines are useful for the prophylaxis and treatment of diabetes, particularly type 2, and its complications, Syndrome X, the various forms of insulin resistance, and hyperlipidaemias, and present reduced side effects, and, particularly, reduced or no liver toxicity.
• Chemo-enzymatic asymmetric synthesis of amino acids. Enantioselective hydrolyses of 2-phenyl-oxazolin-5-ones.
  作者：Rui-Lin Gu、Ik-Soo Lee、Charles J. Sih

  DOI：10.1016/0040-4039(92)88111-h

  日期：1992.4

  Porcine pancreatic lipase and the lipase of Aspergillus niger catalyze the enantioselective hydrolysis of a series of 4-substituted-2-phenyl-oxazolin-5-ones to yield optically active ()-and ()-N-benzoyl amino acids respectively.

  猪胰脂肪酶和黑曲霉的脂肪酶催化一系列4-取代的-2-苯基-恶唑啉-5-酮的对映选择性水解，分别产生光学活性的（）-和（）-N-苯甲酰基氨基酸。
• Genotoxic activity of halogenated phenylglycine derivatives
  作者：Alicia Boto、Juan A. Gallardo、Rosendo Hernández、Francisco Ledo、Ana Muñoz、José R. Murguía、Mauricio Menacho-Márquez、Aurelio Orjales、Carlos J. Saavedra

  DOI：10.1016/j.bmcl.2006.08.111

  日期：2006.12

  The discovery of genotoxic amino acids derived from phenylglycine, and possessing halogen substituents, is described. The utility of hypervalent iodine reagents in the synthesis of this class of compounds is highlighted. The mechanism of action of the (haloaryl)glycines was studied in Saccharomyces cerevisiae.