4-methyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid | 62175-38-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-methyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid
• 英文别名: (S)-4-methyl-2-phenylthiazoline-4-carboxylic acid；4-methyl-2-phenylthiazoline-4-carboxylic acid；4-Thiazolecarboxylic acid, 4,5-dihydro-4-methyl-2-phenyl-；4-methyl-2-phenyl-5H-1,3-thiazole-4-carboxylic acid
• CAS: 62175-38-6
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: FLAKUVQNFZVTSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid 在 草酰氯 作用下， 生成 3-Mercapto-2-methyl-2-[(4-methyl-2-phenyl-4,5-dihydro-thiazole-4-carbonyl)-amino]-propionic acid ethyl ester
  参考文献：
  名称：

  Natural products as pesticides: Two examples of stereoselective synthesis

  摘要：

  The strategy and synthetic efforts leading to efficient stereoselective syntheses of thiangazole, a tris-thiazolinyl-oxazole metabolite isolated from Poly-angium spp., and of hydantocidin, a spironucleoside metabolite isolated from Streptomyces hygroscopicus, are discussed.

  DOI：

  10.1002/(sici)1096-9063(199601)46:1<37::aid-ps339>3.0.co;2-k
• 作为产物：
  描述：

  苯甲亚胺酸乙酯盐酸盐 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 生成 4-methyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Natural products as pesticides: Two examples of stereoselective synthesis

  摘要：

  The strategy and synthetic efforts leading to efficient stereoselective syntheses of thiangazole, a tris-thiazolinyl-oxazole metabolite isolated from Poly-angium spp., and of hydantocidin, a spironucleoside metabolite isolated from Streptomyces hygroscopicus, are discussed.

  DOI：

  10.1002/(sici)1096-9063(199601)46:1<37::aid-ps339>3.0.co;2-k

文献信息

• Process for the preparation of substituted thiazolines and their intermediates
  申请人：——

  公开号：US20030088105A1

  公开（公告）日：2003-05-08

  Process for the preparation of substituted thiazolines of the formula (I) 1 in which Ar is a phenyl, naphthyl, thienyl, pyridyl or quinolinyl radical which can optionally be substituted by one or more substituents from the group consisting of halogen, OH, benzyloxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, COOR 1 where R 1 is H or C 1 -C 4 -alkyl, by coupling of (S)-&agr;-methylcysteine hydrochloride of the formula (II) 2 with a nitrile of the formula (III) Ar—CN in which Ar is as defined above, or a corresponding C 1 -C 4 -alkyl imidate, in which (S)-a-methylcysteine hydrochloride of the formula (II) is reacted in a suitable solvent with a nitrile of the formula (III) or a corresponding C 1 -C 4 -alkyl imidate in the presence of a tertiary base at a pH of 6.5 to 10 at 50° C. up to the reflux temperature to give the corresponding thiazoline of the formula (I), and processes for the preparation of (S)-&agr;-methylcysteine hydrochloride and its use for the preparation of thiazolines of the formula (I).

  制备式(I)的取代噻唑环的过程，其中Ar是苯基、萘基、噻吩基、吡啶基或喹啉基，可以选择性地由卤素、OH、苄氧基、C1-C4烷基、C1-C4烷氧基、COOR1（其中R1为H或C1-C4烷基）中的一个或多个取代基取代，通过(S)-α-甲基半胱氨酸盐酸盐的配对反应，配对反应的反应物为式(II)2和式(III)Ar—CN的腈或相应的C1-C4烷基亚胺，其中(S)-α-甲基半胱氨酸盐酸盐的配对反应物式(II)在适当的溶剂中与式(III)的腈或相应的C1-C4烷基亚胺在三级碱存在下，在pH为6.5至10、50℃至回流温度下反应，得到相应的式(I)的噻唑环，以及制备(S)-α-甲基半胱氨酸盐酸盐的过程及其用于制备式(I)的噻唑环的方法。
• [EN] SYNTHESIS OF 2-ALKYLCYSTEINES, 2-(HYDROXYLATED PHENYL)-4-ALKYLTHIAZOLINE-4-CARBOXYLIC ACIDS AND DERIVATIVES THEREOF<br/>[FR] SYNTHESE DES ACIDES 2-ALKYLCYSTEINES, 2-(PHENYLE HYDROXYLE)-4-ALKYLTHIAZOLINE-4-CARBOXYLIQUES ET DE LEURS DERIVES
  申请人：GENZYME CORP

  公开号：WO2003097622A2

  公开（公告）日：2003-11-27

  The present invention provides methods of preparing 2-alkylcysteine derivatives, many of which can be performed stereoselectively. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. An example of these iron chelating agents are 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-alkyl-thiazole-4-carboxylic acids, such as 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-methyl-thiazole-4-carboxylic acid.

  本发明提供了制备2-烷基半胱氨酸衍生物的方法，其中许多可以进行立体选择性。本发明还披露了一种制备与去铁蒺藜菌素相关的一类铁螯合剂的方法，所有这些铁螯合剂都含有噻唑环。这些铁螯合剂的一个例子是4,5-二氢-2-(2,4-二羟基苯基)-4-烷基噻唑-4-羧酸，例如4,5-二氢-2-(2,4-二羟基苯基)-4-甲基噻唑-4-羧酸。
• Synthesis of 2-alkylcysteine
  申请人：Genzyme Corporation

  公开号：US20030229231A1

  公开（公告）日：2003-12-11

  Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. A method of preparing a 2-alkylcysteine involves condensing cysteine with an aryl nitrile to form a 2-arylthiazoline-4-carboxylic acid, followed by alkylating the 2-arylthiazoline-4-carboxylic acid at the 4-position. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, an aryl nitrile or imidate is condensed with cysteine or a 2-alkyl cysteine.

  非天然氨基酸，例如2-烷基氨基酸，可以合成更多种类的肽类和非肽类药物活性剂。一种制备2-烷基半胱氨酸的方法涉及将半胱氨酸与芳基腈缩合形成2-芳基噻唑啉-4-羧酸，随后在4位烷基化2-芳基噻唑啉-4-羧酸。本发明还揭示了一种制备与去铁胆碱相关的一类含噻唑啉环的铁螯合剂的方法。在这种方法中，芳基腈或咪唑酯与半胱氨酸或2-烷基半胱氨酸缩合。
• Verfahren zur Herstellung von substituierten Thiazolinen und deren Zwischenprodukte
  申请人：DSM Fine Chemicals Austria Nfg GmbH & Co KG

  公开号：EP1302467A2

  公开（公告）日：2003-04-16

  Verfahren zur Herstellung von substituierten Thiazolinen der Formel (1) in der Ar einen Phenyl-, Naphthyl-, Thienyl-, Pyridyl- oder Chinolinylrest bedeuten, der gegebenenfalls durch ein oder mehrere Substituenten aus der Gruppe Halogen, OH, Benzyloxy, C1-C4-Alkyl, C1-C4-Alkoxy, COOR1 mit R1 gleich H oder C1-C4-Alkyl substituiert sein kann, durch Kopplung von (S)-α-Methylcystein-Hydrochlorid der Formel (II) mit einem Nitril der Formel (III)         Ar-CN in der Ar wie oben definiert ist, oder einem korrespondierenden C1-C4-Alkylimidat, bei welchem (S)-α-Methylcystein-Hydrochlorid der Formel (II) in einem geeigneten Lösungsmittel mit an einem Nitril der Formel (III) oder einem korrespondierenden C1-C4-Alkylimidat in Gegenwart einer tertiären Base bei einem pH-Wert von 6.5 bis 10 bei 50°C bis zur Rückflusstemperatur zu dem entsprechenden Thiazolin der Formel (I) umgesetzt wird, sowie Verfahren zur Herstellung von (S)-α-Methylcystein-Hydrochlorid und dessen Verwendung zur Herstellung von Thiazolinen der Formel (I).

  一种制备式（1）取代的噻唑类化合物的工艺 其中 Ar 为苯基、萘基、噻吩基、吡啶基或喹啉基，可任选被卤素、OH、苄氧基、C1-C4-烷基、C1-C4-烷氧基、COOR1（其中 R1 为 H 或 C1-C4-烷基）组成的组中的一个或多个取代基取代、 通过将式（II）的(S)-α-甲基半胱氨酸盐酸盐 与式 (III) 的腈偶联 Ar-CN 式（II）的(S)-α-甲基半胱氨酸盐酸盐在合适的溶剂中与式（III）的腈或相应的 C1-C4 烷基亚氨 酸在叔碱存在下反应，pH 值为 6.5至10、50℃至回流温度下反应，得到相应的式(I)噻唑啉，以及制备(S)-α-甲基半胱氨酸盐酸盐及其用于制备式(I)噻唑啉的工艺。
• Direct α-Lithiation of 4,5-Dihydro-1,3-thiazole-4-carboxylic Acids and Electrophilic Substitution¹
  作者：Waldemar ADAM、Volker EHRIG

  DOI：10.1055/s-1976-24219

  日期：——