(R)-(-)-3-nitromandelic acid | 75172-64-4

• 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)-(-)-3-nitromandelic acid
• 英文别名: (R)-hydroxy-(3-nitro-phenyl)-acetic acid；3-nitro-D-mandelic acid；3-Nitro-D-mandelsaeure；3-Nitro-(R)-(-)-mandelsaeure；(2R)-2-hydroxy-2-(3-nitrophenyl)acetic acid
• CAS: 75172-64-4
• 化学式: C₈H₇NO₅
• mdl: MFCD00041429
• 分子量: 197.147
• InChiKey: KNSULVUQBMUBCX-SSDOTTSWSA-N

物化性质

• 熔点：
  134 °C
• 沸点：
  405.3±35.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (R)-(-)-3-nitromandelic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (6R)-3-acetoxymethyl-7t-[(R)-2-(3-amino-phenyl)-2-hydroxy-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  半合成头孢菌素。7-mandelamido-3-cephem-4-羧酸的合成及其构效关系。

  摘要：

  DOI：

  10.1021/jm00247a008
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (R)-(-)-3-nitromandelic acid
  参考文献：
  名称：

  Fredga; Andersson, Arkiv foer Kemi, 1941, vol. 14B, # 18, p. 2,3

  摘要：

  DOI：

文献信息

• A chemoselective oxidation of monosubstituted ethylene glycol: facile synthesis of optically active α-hydroxy acids
  作者：Kiran Chinthapally、Sundarababu Baskaran

  DOI：10.1039/c4ob00601a

  日期：——

  A mild and efficient method for the synthesis of optically active α-hydroxy acids through chemoselective oxidation of monosubstituted ethylene glycols using the TEMPO–NaOCl reagent system is described. It is evident from our studies that the solvent, pH and reaction temperature are very crucial for the success of this oxidation. The versatility of this method has been demonstrated with a variety of

  描述了一种使用TEMPO-NaOCl试剂系统通过单取代乙二醇的化学选择性氧化合成旋光性α-羟基酸的温和有效方法。从我们的研究中可以明显看出，溶剂，pH和反应温度对于这种氧化的成功至关重要。已经用带有各种官能团的各种脂族，芳族和碳水化合物底物证明了该方法的多功能性。
• Ein einfacher Zugang zu (<i>R</i>)-α-Hydroxycarbonsäuren und (<i>R</i>)- 1-Amino-2-alkoholen aus (<i>R</i>)-Cyanhydrinen
  作者：Thomas Ziegler、Brigitte Hörsch、Franz Effenberger

  DOI：10.1055/s-1990-26945

  日期：——

  A Convenient Route to (R)-α-Hydroxy Carboxylic Acids and (2R)-1-Amino-2-alkanols from (R)-Cyanohydrins (R)-Cyanohyrins, prepared in good to excellent yields with high optical purity by enzyme-catalyzed addition of hydrogen cyanide to aldehydes in organic solvents, are hydrolyzed with concentrated hydrochloric acid at ambient temperature, usually in very high yield, without any trace of racemization to give (R)-α-hydroxy carboxylic acids. Likewise, no racemization is observed by direct reduction of the (R)-cyanohydrins with lithium aluminum hydride to give (2R)-1-amino-2-alkanols.

  一条便捷途径：由(R)-氰醇制备(R)-α-羟基羧酸和(2R)-1-氨基-2-烷醇 通过酶催化氢氰酸与醛在有机溶剂中加成反应制备的(R)-氰醇，具有良好的至极佳的产率和高光学纯度。这些(R)-氰醇在室温下用浓盐酸水解，通常以非常高的产率，且无任何消旋化痕迹，生成(R)-α-羟基羧酸。同样地，通过直接用氢化锂铝还原(R)-氰醇，也未观察到消旋化现象，从而得到(2R)-1-氨基-2-烷醇。
• [EN] SUBSTITUTED alpha -HYDROXY ACID CASPASE INHIBITORS AND THE USE THEREOF<br/>[FR] ACIDES alpha -HYDROXY SUBSTITUES INHIBITEURS DE CASPASES ET LEURS UTILISATIONS
  申请人：CYTOVIA INC

  公开号：WO2001016093A1

  公开（公告）日：2001-03-08

  The present invention is directed to novel substituted α-hydroxy acid thereof, represented by general Formula (I), where R1-R5, X and Z are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are potent inhibitors of caspases and apoptotic cell death. Therefore, the inhibitors of this invention can retard or block cell death in a variety of clinical conditions in which the loss of cells, tissues or entire organs occurs.

  本发明涉及一种新的取代α-羟基酸及其衍生物，其通式表示为（I），其中R1-R5，X和Z的定义如本文所述。本发明还涉及到化合物具有公式（I），是半胱天冬酶和凋亡细胞死亡的有效抑制剂的发现。因此，本发明的抑制剂可以延缓或阻止在细胞、组织或整个器官丢失的多种临床情况中的细胞死亡。
• PROCESS FOR PRODUCING 1,2-ETHANEDIOL DERIVATIVES
  申请人：NITTO CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0816316A1

  公开（公告）日：1998-01-07

  A process for preparing a 1,2-ethanediol derivative in a high yield by reducing an α-hydroxy carboxylic acid ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium boron hydride compound. A process for preparing a 1,2-ethanediol derivative in a high yield by esterifying an α-hydroxy carboxylic acid derivative to synthesize an α-hydroxy carboxylic acid ester derivative, and reducing this ester derivative in a protic solvent or a hydrous aprotic polar solvent in the presence of a sodium borohydride compound in the same reaction vessel.

  一种在氢化硼钠化合物存在下，通过在原生溶剂或含水非丙烯极性溶剂中还原 α-羟基羧酸酯衍生物，以高产率制备 1，2-乙二醇衍生物的工艺。一种通过酯化α-羟基羧酸衍生物合成α-羟基羧酸酯衍生物，并在同一反应容器中，在有硼氢化钠化合物存在的情况下，在质子溶剂或含水非丙烷极性溶剂中还原该酯衍生物，从而高产率制备1，2-乙二醇衍生物的工艺。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE AMINOALCOHOL
  申请人：Mitsubishi Rayon Co., Ltd.

  公开号：EP1219593A1

  公开（公告）日：2002-07-03

  An industrially advantageous process for producing optically active 4-amino-2-methylbutane-1-ol which is useful as an intermediate in synthesizing optically active medicines and pesticides. Racemic 4-amino-2-methylbutane-1-ol is treated with an optically active organic acid. The diastereomeric salt thus obtained is crystallized out and subjected to solid-liquid separation to give optically active 4-amino-2-methylbutane-1-ol. The diastereomeric salt of optically active 4-amino-2-methylbutane-1-ol with an optically active reagent for optical resolution is decomposed by bringing into contact with a solvent and an alkali and subjected to solid-liquid separation, thereby recovering the optically active 4-amino-2-methylbutane-1-ol from the filtrate. Further, the filtration residue containing the alkali salt of the reagent for optical resolution obtained by the solid-liquid separation is brought into contact with a solvent and an acid. Then the reagent for optical resolution thus crystallized out is subjected to solid-liquid separation and recovered.

  一种生产具有光学活性的 4-氨基-2-甲基-1-丁醇的具有工业优势的工艺，该工艺可用作合成具有光学活性的药物和杀虫剂的中间体。外消旋 4-氨基-2-甲基-1-丁醇用光学活性有机酸处理。由此得到的非对映异构盐经结晶和固液分离后，得到具有光学活性的 4-氨基-2-甲基丁烷-1-醇。光学活性 4-氨基-2-甲基丁烷-1-醇的非对映体盐与光学活性试剂进行光学分辨，通过与溶剂和碱接触进行分解，并进行固液分离，从而从滤液中回收光学活性 4-氨基-2-甲基丁烷-1-醇。然后，将含有通过固液分离获得的光学分解试剂碱式盐的过滤残渣与溶剂和酸接触。然后将结晶出的光学分解试剂进行固液分离并回收。