(4R)-2-ethyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester | 373385-36-5

• 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: (4R)-2-ethyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
• 英文别名: methyl (4R)-2-ethyl-4,5-dihydro-1,3-thiazole-4-carboxylate
• CAS: 373385-36-5
• 化学式: C₇H₁₁NO₂S
• 分子量: 173.236
• InChiKey: NCTVKZJCHQITDT-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (4R)-2-ethyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester 在 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate 、 氧气 、 potassium carbonate 、 copper(II) sulfate 、 三氟乙酸 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 20.05h， 生成 methyl (3R)-5-azido-7-methyl-6-[(1-naphthyl)methyl]-4-oxo-1-thia-3a-aza-3-indancarboxylate
  参考文献：
  名称：

  通过硝基插入反应合成多环融合2-吡啶酮：α-突触核蛋白淀粉样蛋白形成的荧光调节剂。

  摘要：

  据报道，一种高效，直接的方法可通过无催化剂，微波辅助的分子内C–H胺化反应合成噻唑-2-吡啶酮嵌入的拟肽多杂环化合物。评价所有合成的多杂环化合物的荧光性质以及对α-突触核蛋白淀粉样蛋白形成的影响。

  DOI：

  10.1021/acs.orglett.5b03190
• 作为产物：
  描述：

  ethyl propanimidate hydrochloride 、 L-半胱氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (4R)-2-ethyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester 、 (4S)-2-ethyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  An Enantioselective Ketene−Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones

  摘要：

  Previously, a method for the stereoselective synthesis of P-lactams, starting from 2H-Delta (2)-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-Delta (2)-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 --> 78 degreesC. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 --> 64 degreesC led to the desired 2-pyridinones;in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different Delta (2)-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.

  DOI：

  10.1021/jo015794u

文献信息

• Microwave-assisted decarboxylation of bicyclic 2-pyridone scaffolds and identification of Aβ-peptide aggregation inhibitors
  作者：Veronica Åberg、Fredrik Norman、Erik Chorell、Andreas Westermark、Anders Olofsson、A. Elisabeth Sauer-Eriksson、Fredrik Almqvist

  DOI：10.1039/b503294f

  日期：——

  A reagent-free microwave-assisted decarboxylation procedure for carboxylic acid functionalized bicyclic 2-pyridones has been developed. This new method, based on microwave heating at 220 °C for 600 seconds in N-methyl pyrrolidone (NMP), proved to be practical and very efficient, resulting in decarboxylated 2-pyridones in near-quantitative yields. The decarboxylated products and the intermediate 2-pyridones in the form of carboxylic acid methyl esters and carboxylic acids were screened for their effect on Aβ-peptide aggregation. Two out of the 21 2-pyridones described in this study inhibited amyloid formation of the Alzheimer Aβ(1–40) peptide. The effect was seen even at a 4 : 1 ratio of 2-pyridone and monomeric Aβ-peptide.

  开发了一种无试剂的微波辅助去羧化程序，用于羧酸功能化的双环2-吡啶酮。该新方法基于在N-甲基吡咯烷酮（NMP）中以220°C加热600秒，证明实用且非常高效，产生的去羧化2-吡啶酮几乎定量。去羧化产品和羧酸甲酯及羧酸形式的中间体2-吡啶酮被筛选以研究其对Aβ肽聚集的影响。在本研究中描述的21种2-吡啶酮中，有两种抑制了阿尔茨海默病Aβ(1–40)肽的淀粉样蛋白形成。即使在2-吡啶酮与单体Aβ肽的比率为4:1时，仍观察到了这种效果。
• 2,3-Dihydro-Thiazolo[3,2-A]Pyridin-5-One Derivatives, Intermediates Thereof, and Their Use as Antibacterial Agents
  申请人：Quretech Bio AB

  公开号：US20170334931A1

  公开（公告）日：2017-11-23

  The disclosure relates to certain novel substituted ring-fused thiazolino 2-pyridines of Formula I, to processes for preparing such compounds, to their use in treating a bacterial infection such as Chlamydia infection, to methods for their therapeutic use and to pharmaceutical compositions containing them.
• An Enantioselective Ketene−Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones
  作者：Hans Emtenäs、Lisa Alderin、Fredrik Almqvist

  DOI：10.1021/jo015794u

  日期：2001.10.1

  Previously, a method for the stereoselective synthesis of P-lactams, starting from 2H-Delta (2)-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-Delta (2)-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 --> 78 degreesC. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 --> 64 degreesC led to the desired 2-pyridinones;in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different Delta (2)-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.
• Synthesis of Multiring Fused 2-Pyridones via a Nitrene Insertion Reaction: Fluorescent Modulators of α-Synuclein Amyloid Formation
  作者：Pardeep Singh、Erik Chorell、K. Syam Krishnan、Tomas Kindahl、Jörgen Åden、Pernilla Wittung-Stafshede、Fredrik Almqvist

  DOI：10.1021/acs.orglett.5b03190

  日期：2015.12.18

  catalyst-free, microwave-assisted, intramolecular C–H amination reaction is reported. All the synthesized polyheterocycles were evaluated for their fluorescent properties and effect on α-synuclein amyloid formation.

  据报道，一种高效，直接的方法可通过无催化剂，微波辅助的分子内C–H胺化反应合成噻唑-2-吡啶酮嵌入的拟肽多杂环化合物。评价所有合成的多杂环化合物的荧光性质以及对α-突触核蛋白淀粉样蛋白形成的影响。