2-甲基-4,5-二氢-1,3-噻唑-4-羧酸甲酯 | 2519-89-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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
• 中文名称: 2-甲基-4,5-二氢-1,3-噻唑-4-羧酸甲酯
• 英文名称: (4R)-2-methyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
• 英文别名: L-2-Methyl-4-methoxycarbonyl-Δ²-thiazolin；(4R)-4-methoxycarbonyl-2-methyl-2-thiazoline；(R)-4-(methoxycarbonyl)-2-methyl-thiazoline；(3R)-2-methyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester；(R)-2-methyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester；methyl (R)-2-methyl-4,5-dihydrothiazole-4-carboxylate；methyl (4R)-2-methyl-4,5-dihydro-1,3-thiazole-4-carboxylate
• CAS: 2519-89-3
• 化学式: C₆H₉NO₂S
• 分子量: 159.209
• InChiKey: GRNYICVXEZMNSA-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-4,5-二氢-1,3-噻唑-4-羧酸甲酯 在 盐酸 、 水 作用下， 反应 24.0h， 以94%的产率得到L-半胱氨酸盐酸盐无水物
  参考文献：
  名称：

  Efficient synthesis of primary 2-aminothiols from 2-aminoalcohols and methyldithioacetate

  摘要：

  Various primary 2-aminothiols have been prepared by a general and efficient method, in three steps, starting from commercially available 2-aminoalcohols and methyldithioacetate as a convenient source of sulfur. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.014
• 作为产物：
  描述：

  methyl (2S)-2-(ethanethioylamino)-3-hydroxypropanoate 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到2-甲基-4,5-二氢-1,3-噻唑-4-羧酸甲酯
  参考文献：
  名称：

  Efficient synthesis of primary 2-aminothiols from 2-aminoalcohols and methyldithioacetate

  摘要：

  Various primary 2-aminothiols have been prepared by a general and efficient method, in three steps, starting from commercially available 2-aminoalcohols and methyldithioacetate as a convenient source of sulfur. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.014

文献信息

• One-Pot Synthesis of 2,4-Disubstituted Thiazoline from β-Azido Disulfide and Carboxylic Acid
  作者：Yi Liu、Jun Liu、Xiangbing Qi、Yuguo Du

  DOI：10.1021/jo301030k

  日期：2012.8.17

  A concise and efficient one-pot four-step synthesis of 2,4-disubstituted thiazoline via a cascade disulfide bond cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction is established. Treatment of various carboxylic acids with β-azido disulfides under this one-pot procedure obtained the desired thiazolines in good to excellent isolated yields.

  建立了通过级联二硫键裂解/硫代羰基化/施陶丁格还原/氮杂-维蒂希反应的2,4-二取代噻唑啉的简洁高效的一锅四步合成方法。在该一锅法中，用β-叠氮基二硫化物处理各种羧酸可得到所需的噻唑啉，分离产率高至优异。
• Versatile Synthesis of Secondary 2-Amino Thiols and/or Their Disulfides via Thiazolinium Salts
  作者：Guillaume Mercey、Jean-François Lohier、Annie-Claude Gaumont、Jocelyne Levillain、Mihaela Gulea

  DOI：10.1002/ejoc.200900514

  日期：2009.9

  Commercially available β-amino alcohols have been transformed into various secondary β-amino thiols and/or their disulfides by using methyl dithioacetate as a source of sulfur. The transformation involves a thiazolinium salt as a versatile key intermediate, which enables easy modulation of the product structure by varying the substituents on the heterocycle and the N-alkylating agent.(© Wiley-VCH Verlag

  通过使用二硫代乙酸甲酯作为硫源，已将市售的 β-氨基醇转化为各种仲 β-氨基硫醇和/或其二硫化物。该转化涉及作为通用关键中间体的噻唑啉盐，它可以通过改变杂环和 N-烷基化剂上的取代基轻松调节产品结构。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany , 2009)
• Synthesis of Densely Functionalized <i>N</i>-Alkenyl 2-Pyridones via Benzyne-Induced Ring Opening of Thiazolino-Fused 2-Pyridones
  作者：Pardeep Singh、Andrew G. Cairns、Dan E. Adolfsson、Jörgen Ådén、Uwe H. Sauer、Fredrik Almqvist

  DOI：10.1021/acs.orglett.9b02549

  日期：2019.9.6

  We report the synthesis of 6-arylthio-substituted-N-alkenyl 2-pyridones by ring opening of bicyclic thiazolino-2-pyridones with arynes. Varied functionalization was used to investigate scope and substituent influences on reactivity. Selected conditions favor thioether ring opening over [4 + 2] cycloaddition and an unusual aryne incorporating ring expansion. Deuterium labeling was used to clarify observed

  我们报告了与芳烃的双环噻唑啉-2-吡啶酮的开环反应，合成了6-芳硫基取代的-N-烯基2-吡啶酮。各种功能化用于研究范围和取代基对反应性的影响。选定的条件比[4 + 2]环加成更有利于硫醚开环，并且不寻常的芳烃具有扩环功能。氘标记用于澄清观察到的反应性。利用这些知识，我们制备了具有复杂取代模式的类药物分子，并展示了硫醚开环如何可用于具有竞争反应性的支架上。
• Cu(<scp>i</scp>)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates: synthesis of 4,4′-bithiazoline derivatives
  作者：Xinxin Fang、Kaifan Zhang、Hequan Yao、Yue Huang

  DOI：10.1039/c6ob01471b

  日期：——

  Cu(I)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates with good functional group tolerance has been developed. The methodology presented an efficient method to directly construct vicinal carbon-hetero quaternary centers existing in numerous functional molecules and could be applied to the synthesis of 4,4′-bithiazoles which are difficult to prepare by direct C–H activation.

  已经开发了具有良好官能团耐受性的Cu（I）催化的噻唑啉-4-羧酸酯的氧化均偶联剂。该方法学提供了一种直接构建存在于众多功能分子中的邻近碳杂四元中心的有效方法，可用于合成难以通过直接C–H活化制备的4,4'-联噻唑。
• Regioselective Halogenations and Subsequent Suzuki−Miyaura Coupling onto Bicyclic 2-Pyridones
  作者：Christoffer Bengtsson、Fredrik Almqvist

  DOI：10.1021/jo902458g

  日期：2010.2.5

  A selective synthesis of 6-bromo-8-iodo dihydro thiazolo ring-fused 2-pyridones is described. These halogenated 2-pyridones are selectively arylated by sequential Suzuki−Miyaura couplings. This approach can advantageously be used to synthesize focused libraries of substituted ring-fused 2-pyridones, a class of compounds with novel antibacterial properties.

  描述了6-溴-8-碘二氢噻唑环稠合的2-吡啶酮的选择性合成。这些卤化的2-吡啶酮通过顺序的Suzuki-Miyaura偶联选择性地芳基化。该方法可以有利地用于合成取代的环稠合的2-吡啶酮的聚焦库，取代的环稠合的2-吡啶酮是一类具有新型抗菌特性的化合物。