2-羟基-3-(2-硝基-苯基)-丙酸 | 104145-71-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 2-羟基-3-(2-硝基-苯基)-丙酸
• 英文名称: 2-hydroxy-3-(2-nitro-phenyl)-propionic acid
• 英文别名: α-Oxy-β-(2-nitro-phenyl)-propionsaeure；2-Hydroxy-3-(2-nitro-phenyl)-propionsaeure；β-(2-Nitro-phenyl)-milchsaeure；2-Nitro-α-oxy-hydrozimtsaeure；α-hydroxy-2-nitrobenzenepropanoic acid；alpha-hydroxy-2-nitrobenzenepropanoic acid；2-Hydroxy-3-(2-nitrophenyl)propanoic acid
• CAS: 104145-71-3；106025-39-2；106025-44-9
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: IEHZEDWCLJYWMU-UHFFFAOYSA-N

物化性质

• 沸点：
  411.1±30.0 °C(Predicted)
• 密度：
  1.475±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-羟基-3-(2-硝基-苯基)-丙酸 在 sodium hydroxide 作用下， 生成 甲基硝基苯
  参考文献：
  名称：

  Jaenisch, Chemische Berichte, 1923, vol. 56, p. 2450

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-硝基苯基)丙酸 在 磷化氢 、 溴 、 silver nitrate 作用下， 生成 2-羟基-3-(2-硝基-苯基)-丙酸
  参考文献：
  名称：

  Jaenisch, Chemische Berichte, 1923, vol. 56, p. 2450

  摘要：

  DOI：

文献信息

• Process for preparing indoline-2-carboxylic acids via
  申请人：American Home Products Corporation

  公开号：US04585879A1

  公开（公告）日：1986-04-29

  Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivatives thereof) comprising the following steps: (a) reducing .alpha.-oxo-2-nitrobenzenepropanoic acid to .alpha.-hydroxy-2-nitrobenzenepropanoic acid, (b) replacing the hydroxyl group of the latter with a chlorine atom utilizing a selected Vilsmeier chlorinating reagent at temperatures of at least 20.degree. C., (c) reducing the nitro group of the resulting .alpha.-chloro-2-nitrobenzenepropanoic acid to obtain .alpha.-chloro-2-aminobenzenepropanoic acid, and (d) cyclizing the latter in aqueous base to form the desired indoline-2-carboxylic acid. Alternately, steps (c) and (d) may be combined in a one pot step by using, for example, a Raney nickel-hydrazine reducing medium.

  披露的是一种获取吲哚-2-羧酸（或其衍生物）的过程，包括以下步骤：(a)将α-氧代-2-硝基苯丙酸还原为α-羟基-2-硝基苯丙酸，(b)利用选定的Vilsmeier氯化试剂，在至少20℃的温度下，将后者的羟基替换为氯原子，(c)将得到的α-氯-2-硝基苯丙酸的硝基还原为α-氯-2-氨基苯丙酸，以及(d)将后者在碱性水溶液中环合以形成所需的吲哚-2-羧酸。另外，步骤(c)和(d)可以通过使用例如Raney镍-肼还原介质，在一个锅中步骤合并。
• Process for the asymmetric synthesis of chiral indoline-2-carboxylic
  申请人：American Home Products Corporation

  公开号：US04614806A1

  公开（公告）日：1986-09-30

  Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises: (a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV; (b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.degree. C., in order to obtain, respectively, and (R) or (S)-.alpha.-chloro-2-nitrobenzenepropanoic acid IV; (c) reducing the nitro group of said (R) or (S)-.alpha.-chloro-2-nitrobenzenepropanoic acid (V) to an amino group; and (d) cyclizing the resulting (R) or (S)-.alpha.-chloro-2-aminobenzenepropanoic acid in aqueous base.

  本文披露了一种制备结构式为：##STR1## 其中X为氢、溴、氯、C.sub.1-4烷基或C.sub.1-4烷氧基的不对称吲哚-2-羧酸的方法，包括：(a)将o-硝基苯丙酮酸III与(R)-脯氨酸或(S)-脯氨酸及硼氢化钠在惰性溶剂中形成还原复合物，分别得到(S)或(R)-α-羟基-2-硝基苯丙酸IV；(b)将(S)或(R)-α-羟基-2-硝基苯丙酸III与Vilsmeier氯化试剂反应，其中其氯化试剂选择自硫酰氯、草酰氯、氧氯化磷、五氯化磷和磺酰氯的一组，其酰胺选择自二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺和二乙基乙酰胺的一组，反应温度至少为20°C，以分别获得(R)或(S)-α-氯-2-硝基苯丙酸IV；(c)还原(R)或(S)-α-氯-2-硝基苯丙酸(V)的硝基为氨基；(d)在水性碱中使所得的(R)或(S)-α-氯-2-氨基苯丙酸环化。
• Process for the asymmetric synthesis of chiral
  申请人：American Home Products Corporation

  公开号：US04727183A1

  公开（公告）日：1988-02-23

  Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises: (a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV; (b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.degree. C., in order to obtain, respectively, and (R) or (S)-.alpha.-chloro-2-nitrobenzenepropanoic acid IV; (c) reducing the nitro group of said (R) or (S)-.alpha.-chloro-2-nitrobenzenepropanoic acid (V) to an amino group; and (d) cyclizing the resulting (R) or (S)-.alpha.-chloro-2-aminobenzenepropanoic acid in aqueous base.

  本文公开了一种制备不对称吲哚-2-羧酸的方法，其结构式为：##STR1## 其中X为氢、溴、氯、C.sub.1-4烷基或C.sub.1-4烷氧基，包括以下步骤：(a)将o-硝基苯丙酮酸III与(R)-脯氨酸或(S)-脯氨酸及氢化硼钠在惰性溶剂中形成还原复合物，以非对称还原的方式，分别形成(S)或(R)-α-羟基-2-硝基苯丙酸IV；(b)将(S)或(R)-α-羟基-2-硝基苯丙酸IV与维尔斯迈尔氯化试剂反应，所述氯化试剂的氯化剂选自一组，包括氯化硫酰、草酰氯、氧化三磷酰、五氯化磷和氯化亚磺基，其酰胺选自一组，包括二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺和二乙基乙酰胺，在至少20°C的温度下进行反应，以分别获得(R)或(S)-α-氯-2-硝基苯丙酸IV；(c)还原(R)或(S)-α-氯-2-硝基苯丙酸(V)的硝基基团为氨基基团；(d)在水性碱中环化所得的(R)或(S)-α-氯-2-氨基苯丙酸。
• WO2006/113432
  申请人：——

  公开号：——

  公开（公告）日：——
• Deracemisation of aryl substituted α-hydroxy esters using Candida parapsilosis ATCC 7330: effect of substrate structure and mechanism
  作者：B. Baskar、N.G. Pandian、K. Priya、Anju Chadha

  DOI：10.1016/j.tet.2005.09.104

  日期：2005.12

  Candida parapsilosis ATCC 7330 was found to be an efficient biocatalyst for the deracemisation of aryl alpha-hydroxy esters (65-85% yield and 90-99% ee). A variety of aryl and aryl substituted alpha-hydroxy esters were synthesized to reflect steric and electronic effects on biocatalytic deracemisation. The mechanism of this biocatalytic deracemisation was found to be stereoinversion. (c) 2005 Elsevier Ltd. All rights reserved.