(2S)-2-羟基-2-甲基-3-苯丙酸 | 164333-77-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (2S)-2-羟基-2-甲基-3-苯丙酸
• 英文名称: (S)-α-methylphenyllactic acid
• 英文别名: (S)-2-hydroxy-2-methyl-3-phenylpropanoic acid；(-)-2-Hydroxy-2-methyl-3-phenylpropionsaeure；(S)-2-hydroxy-2-methyl-3-phenyl-propionic acid；(S)-2-Hydroxy-2-methyl-3-phenyl-propionsaeure；(2S)-2-hydroxy-2-methyl-3-phenylpropanoic acid
• CAS: 164333-77-1
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: IBIBMVNOBCIJNU-JTQLQIEISA-N

物化性质

• 沸点：
  333.5±22.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  (2S)-2-羟基-2-甲基-3-苯丙酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 61.5h， 生成 (S)-Hippuryl-alpha-methylphenyllactic acid
  参考文献：
  名称：

  Hippuryl-α-methylphenylalanine and hippuryl-α-methylphenyllactic acid as substrates for carboxypeptidase A. Syntheses, kinetic evaluation and mechanistic implication

  摘要：

  (R)- and (S)-Hippuryl-alpha-methylphenylalanine [(R)- and (S)-Hipp-alpha-MePhe] and (S)-hippuryl-alpha-methylphenyllactic acid [(S)-Hipp-alpha-MeOPhe] were synthesized and evaluated as substrates for carboxypeptidase A (CPA) in an effort to shed further light on the catalytic mechanism of the enzyme. The rate of CPA-catalyzed hydrolysis of (S)-Hipp-alpha-MePhe was reduced by 105-fold compared with that of (S)-Hipp-Phe. but the hydrolysis rate of (S)-Hipp-OPhe was lowered by only 6.8-fold by the introduction of a methyl group at the alpha-position. (R)-Hipp-alpha-MePhe failed to be hydrolyzed initially, then started to undergo hydrolysis in about 2 h at a much reduced rate. The results of present study may be envisioned on the basis of the proposition that while peptide substrate is hydrolyzed via a tetrahedral transition state formed by the attack of the zinc-bound water molecule at the peptide carbonyl carbon, ester hydrolysis takes the path that involves an anhydride intermediate generated by the attack of the carboxylate of Glu-270 at the ester carbonyl carbon, (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00006-7
• 作为产物：
  描述：

  (R,S)-2-hydroxy-2-methyl-3-phenylpropanoic acid 在 马钱子碱 作用下， 生成 (2S)-2-羟基-2-甲基-3-苯丙酸
  参考文献：
  名称：

  Davies et al., Journal of the Chemical Society, 1957, p. 3154,3156

  摘要：

  DOI：

文献信息

• [EN] ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS<br/>[FR] COMPOSÉS DEPSIPEPTIDIQUES ANTHELMINTHIQUES
  申请人：MERIAL INC

  公开号：WO2018093920A1

  公开（公告）日：2018-05-24

  The present invention provides cyclic depsipeptide compounds of formula (I) wherein the stereochemical configuration of at least one carbon atom bearing the groups Cy1, Cy2, R1, R2, R3, R4, Ra and Rb is inverted compared with the naturally occurring cyclic depsipeptide PF1022A. The invention also provides compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

  本发明提供了公式（I）的环状脱氨肽化合物，其中至少一个碳原子的立体化学构型与自然存在的环状脱氨肽PF1022A的基团Cy1、Cy2、R1、R2、R3、R4、Ra和Rb相比发生了倒置。该发明还提供了包含这些化合物的组合物，对危害动物的寄生虫具有有效性。这些化合物和组合物可用于对抗哺乳动物和鸟类体内或体表的寄生虫。该发明还提供了一种改进的方法，用于根除、控制和预防鸟类和哺乳动物的寄生虫感染。
• Method and compositions for identifying anti-HIV therapeutic compounds
  申请人：GILEAD SCIENCES, INC.

  公开号：US20040121316A1

  公开（公告）日：2004-06-24

  Methods are provided for identifying anti-HIV therapeutic compounds substituted with carboxyl ester or phosphonate ester groups. Libraries of such compounds are screened optionally using the novel enzyme GS-7340 Ester Hydrolase. Compositions and methods relating to GS-7340 Ester Hydrolase also are provided.

  提供了一种鉴定含有羧酸酯或磷酸酯基团抗HIV治疗化合物的方法。可以选择使用新型酶GS-7340酯水解酶筛选这类化合物的文库。还提供了与GS-7340酯水解酶相关的组合物和方法。
• [EN] SPIRO-OXAZOLONES<br/>[FR] SPIRO-OXAZOLONES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015124541A1

  公开（公告）日：2015-08-27

  The present invention provides spiro-oxazolones, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments. The present compounds are useful as therapeutics acting peripherally and centrally in the conditions of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.

  本发明提供了螺环噁唑酮，其作为V1a受体调节剂，特别是作为V1a受体拮抗剂，其制备方法，含有它们的药物组合物以及它们作为药物的用途。本化合物在周围和中枢作用下，对于不当分泌加压素、焦虑、抑郁症、强迫症、自闭症谱系障碍、精神分裂症、攻击性行为和相位错位性睡眠障碍，特别是时差反应等症状的治疗具有用处。
• Electrophilic asymmetric syntheses of α-hydroxy carboxylic acids
  作者：Jerry W. Ludwig、Martin Newcomb、David E. Bergbreiter

  DOI：10.1016/s0040-4039(00)84629-8

  日期：——

  Asymmetric electrophilic synthesis of α-hydroxy carboxylic acids from chiral amide derivatives of tert-butyl- and trialkylsilyl- protected glycolic and lactic acids are described which lead to chiral α-hydroxy carboxylic acids in 60–95% diastereomic excess.

  描述了由叔丁基和三烷基甲硅烷基保护的乙醇酸和乳酸的手性酰胺衍生物的不对称亲电合成α-羟基羧酸，导致非手性过量60-95％的手性α-羟基羧酸。
• Aymmetric synthesis of () - and ()-citramalate in high enantiomeric purity
  作者：Stephen V. Frye、Ernest L. Eliel

  DOI：10.1016/s0040-4039(00)98684-2

  日期：1985.1

  An asymmetric synthesis of both isomers of dimethyl 2-acetoxycitramalate in over 96% enantiomeric excess is described.

  描述了2-乙酰氧基柠檬酸二甲酯的两种异构体的不对称合成，其对映体过量超过96％。