Ethyl 2-(4-methoxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylate | 1332708-68-5

• 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: Ethyl 2-(4-methoxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylate
• CAS: 1332708-68-5
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: BRGUHAIKHFLUIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(4-methoxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylate 在 氧气 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以83%的产率得到2-(4-甲氧基苯基)-噻唑-4-羧酸乙酯
  参考文献：
  名称：

  Copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles

  摘要：

  A mild copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles has been developed. Various substrates with alkyl or aryl substitutions at 2-position on azoline ring could be smoothly oxidized to the desired products in good to excellent yields. Moreover, the hydrolysis of the ester group could be avoided under this method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.016

文献信息

• [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 substituted thiazoline carboxylic acids
  申请人：Genzyme Corporation

  公开号：US20040082796A1

  公开（公告）日：2004-04-29

  A useful and efficient method of preparing an alkylated thiazoline carboxylic acid, or a derivative thereof, comprises coupling a substituted aryl nitrile such as, for example, 2,4-dimethoxybenzonitrile or 4-methoxybenzonitrile, with a cysteine ester to form a substituted thiazoline carboxylic acid ester; optionally hydrolyzing the substituted thiazoline carboxylic acid ester to form a substituted thiazoline carboxylic acid; optionally, protecting the carboxyl group; alkylating the thiazoline ring at the 4-carbon position, as indicated in Structural Formula (I), with a compound of the formula R 1 —L, wherein R 1 is as defined above and L is a leaving group, in the presence of a phase transfer catalyst; and, optionally, deprotecting the carboxyl group. In one embodiment of the present invention, a cinchona-alkaloid derived phase transfer catalyst is used to alkylate a protected substituted thiazoline carboxylic acid.

  一种制备烷基化噻唑啉羧酸或其衍生物的有用且高效方法包括：将取代芳基腈（例如2,4-二甲氧基苯腈或4-甲氧基苯腈）与半胱氨酸酯偶合形成取代噻唑啉羧酸酯；可选择水解取代噻唑啉羧酸酯形成取代噻唑啉羧酸；可选择保护羧基；在相转移催化剂存在下，用式R1-L的化合物烷基化噻唑啉环的4-碳位，如结构式（I）所示，其中R1如上所定义，L是一个离去基团；可选择去保护羧基。在本发明的一种实施例中，使用奎宁生物碱衍生的相转移催化剂烷基化保护的取代噻唑啉羧酸。
• SYNTHESIS OF 2-ALKYLCYSTEINES, 2-(HYDROXYLATED PHENYL)-4-ALKYLTHIAZOLINE-4-CARBOXYLIC ACIDS AND DERIVATIVES THEREOF
  申请人：Genzyme Corporation

  公开号：EP1529037A2

  公开（公告）日：2005-05-11
• US6982335B2
  申请人：——

  公开号：US6982335B2

  公开（公告）日：2006-01-03
• US7285670B2
  申请人：——

  公开号：US7285670B2

  公开（公告）日：2007-10-23