间羟基-2-羰基丙酸 | 4607-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 间羟基-2-羰基丙酸
• 英文名称: 3-hydroxy-α-oxo-benzenepropanoic acid
• 英文别名: 3-hydroxyphenylpyruvic acid；<3-Hydroxy-phenyl>-brenztraubensaeure；(3-Hydroxy-phenyl)-brenztraubensaeure；α-Oxo-β-(3-oxy-phenyl)-propionsaeure；3-(3-Hydroxyphenyl)-2-oxopropanoic acid
• CAS: 4607-41-4
• 化学式: C₉H₈O₄
• 分子量: 180.16
• InChiKey: PNYWALDMLUDDTA-UHFFFAOYSA-N

物化性质

• 熔点：
  165 °C (decomp)
• 沸点：
  383.0±25.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  间羟基-2-羰基丙酸 在 iron sulfide 、 碳酸氢铵 作用下， 以 水 为溶剂， 反应 336.0h， 以45%的产率得到DL-间酪氨酸
  参考文献：
  名称：

  Primordial Amino Acids by Reductive Amination of α-Oxo Acids in Conjunction with the Oxidative Formation of Pyrite

  摘要：

  DOI：

  10.1016/00404-0399(50)10086-
• 作为产物：
  描述：

  4-(3-acetoxy-benzylidene)-2-methyl-4H-oxazol-5-one 在 盐酸 作用下， 生成 间羟基-2-羰基丙酸
  参考文献：
  名称：

  Acheson, Journal of the Chemical Society, 1957, p. 499

  摘要：

  DOI：

文献信息

• A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A
  作者：Jean Paul Bourgault、Amarendar Reddy Maddirala、Peter R. Andreana

  DOI：10.1039/c4ob01148a

  日期：——

  The herbicide (±)-thaxtomin A has been synthesized in a one-pot two step process through an Ugi reaction followed by base-mediated cyclization.

  除草剂(±)-thaxtomin A已经通过一锅两步法合成，该方法是通过Ugi反应后进行碱介导的环化反应。
• Preparation of prodrugs for selective drug delivery
  申请人：Mills L. Randell

  公开号：US20050080260A1

  公开（公告）日：2005-04-14

  Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。
• Total Synthesis of Thaxtomin A and Its Stereoisomers and Findings of Their Biological Activities
  作者：Hongbo Zhang、Xin Ning、Hang Hang、Xuyan Ru、Haichen Li、Yonghong Li、Lizhong Wang、Xiao Zhang、Shujing Yu、Yuanyuan Qiao、Xin Wang、Peng George Wang

  DOI：10.1021/ol4026556

  日期：2013.11.15

  The first and facile total synthesis of thaxtomin A and its three stereoisomers has been achieved. The synthetic approach involves intramolecular nucleophilic cyclization of an amide toward a ketoamide group to produce a C-hydroxydiketopiperazine scaffold. The most amazing discovery was that each of the four stereoisomers of TA exhibits different phytotoxic, fungicidal, and antiviral activities.

  已经成功实现了纤溶酶A及其三种立体异构体的首次合成。合成方法涉及酰胺向酮酰胺基团的分子内亲核环化，以产生C-羟基二酮哌嗪骨架。最令人惊讶的发现是，TA的四种立体异构体中的每一种均表现出不同的植物毒，杀真菌和抗病毒活性。
• Process for the preparation of halogenated beta-lactam compounds
  申请人：BIOCHIMICA OPOS SPA

  公开号：EP0570058A2

  公开（公告）日：1993-11-18

  There is described the preparation of halogenated ß-lactam derivatives by introduction of a chlorine atom in the 3-position of the cephem nucleus starting from a 3-sulfonyloxycephem. Such starting materials are reacted with a chlorine ions donor in a basic medium.

  这里介绍了一种卤化 ß-内酰胺衍生物的制备方法，即从 3-磺酰氧基头孢烷开始，在头孢烷核的 3 位引入一个氯原子。这种起始材料在碱性介质中与氯离子供体发生反应。
• Process for production of phenyllactic acid derivative
  申请人：NITTO CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0696566A1

  公开（公告）日：1996-02-14

  A process for producing a phenyllactic acid derivative comprises hydrogenating a phenylpyruvic acid derivative in the presence of a catalyst containing at least one element selected from the Group VIII elements of the periodic table. The process provides a phenyllactic acid derivative useful as an intermediate in the production of pharmaceuticals and agricultural chemicals. The process uses as a starting material a phenylpyruvic acid derivative which is easily synthesized. The process is simpler in operation and provides a higher yield than conventional processes.

  生产苯乳酸衍生物的工艺包括在含有至少一种选自元素周期表第八族元素的催化剂存在下氢化苯丙酮酸衍生物。该工艺提供了一种苯基乳酸衍生物，可用作生产药品和农药的中间体。该工艺使用易于合成的苯丙酮酸衍生物作为起始原料。与传统工艺相比，该工艺操作简单，产率高。