(4R)-2-phenyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester | 3113-46-0

• 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-phenyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
• 英文别名: 4-carbomethoxy-2-phenyl-δ²-thiazoline；(R)-2-phenyl-4-methoxycarbonyl-4,5-dihydrothiazole；methyl 2-phenyl-4,5-dihydrothiazole-4-carboxylate；L-2-Phenyl-4-methoxycarbonyl-Δ²-thiazolin；(R)-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester；S,N-phenylmethanylylidene-L-cysteine methyl ester；methyl 2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylate；methyl (R)-2-phenyl-4,5-dihydrothiazole-4-carboxylate；(4R)-4-methoxycarbonyl-2-phenyl-2-thiazoline；Methyl (4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylate
• CAS: 3113-46-0
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: ZJGPNHWFWJZYHJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-phenyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester 在 氨 作用下， 以 甲醇 为溶剂， 生成 2-Phenyl-2-thiazolin-4-carboxamid
  参考文献：
  名称：

  结构变化对δ-2-噻唑啉水解的影响。

  摘要：

  DOI：

  10.1021/ja01090a036
• 作为产物：
  描述：

  硫代苯甲酸 S-苯基酯 在 劳森试剂 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 甲苯 为溶剂， 反应 6.5h， 生成 (4R)-2-phenyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Compound embodiments that release H2S by reaction with a reactive compound and methods of making and using the same

  摘要：

  本文揭示了一种供体化合物的实施例，通过与反应性化合物发生反应释放H2S。本文描述的供体化合物实施例可用于向受试者或样品释放H2S，并且进一步可用于给药治疗剂。供体化合物实施例还可以促进生物共轭。还公开了制备和使用供体化合物实施例的方法。

  公开号：

  US11078157B1

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。
• The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
  作者：Maria J. Petersson、Ian D. Jenkins、Wendy A. Loughlin

  DOI：10.1039/b818310d

  日期：——

  β-Hydroxy amides6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time,

  β-羟基酰胺6和7用三苯基anhydride酸酐三氟甲烷磺酸盐（3）或环状类似物4在温和条件下产生2-恶唑啉5和8。通过检查试剂3或4或二异丙基乙胺的当量数来优化反应，以达到最佳环化效果。还研究了改变反应温度，反应时间，浓度，溶剂和添加速率的影响。然而，发现使用三苯甲基来封闭起始酰胺的羟基或硫醇基团上的反应，以及随后在不存在碱的情况下进行原位去三苯甲基化反应，可以大大提高收率。试剂4 在提纯产品方面具有显着优势，可用于脱水一系列三苯甲基衍生物，以高产率（85-99％）生成四恶唑啉，噻唑啉和二氢-1,3-恶嗪，以及四氢呋喃。 -1,3-奥氮平（31％）。
• 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。
• Indole grignard reaction. III. Synthesis, crystal structure, and anglgesic activity of (R)- and (S)-3-amino-2,3,4,9-tetrahydrothiopyrano(2,3-b)indoles.
  作者：Natsuki ISHIZUKA、Tomohiro SATO、Yasuo MAKISUMI

  DOI：10.1248/cpb.38.1396

  日期：——

  the crystal structure of one of them was determined by X-ray crystallography. The indole Grignard reaction was effective for synthesizing the key intermediate of the (R)-isomers. The analgesic activities of the products were compared with those of 4-methylaminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (1), Isoxal, and Tiaramide. The (R)-isomers were more potent than the corresponding (S)-isomers

  合成了标题化合物的两种对映体，并通过X射线晶体学测定了其中一种的晶体结构。吲哚格氏试剂对于合成（R）-异构体的关键中间体是有效的。将产品的镇痛活性与4-甲基氨基甲基-2,3,4,9-四氢硫代吡喃并[2,3-b]吲哚（1），Isoxal和Tiaramide的镇痛活性进行了比较。（R）异构体比相应的（S）异构体更有效，并且比Isoxal和Tiaramide更有效，但比1。
• Design and Synthesis of New 2-Aryl-4,5-Dihydro-thiazole Analogues: In Vitro Antibacterial Activities and Preliminary Mechanism of Action
  作者：Fangfang Tan、Baojun Shi、Jian Li、Wenjun Wu、Jiwen Zhang

  DOI：10.3390/molecules201119680

  日期：——

  Sixty 2-aryl-4,5-dihydrothiazoles were designed and synthesized in yields ranging from 64% to 89% from cysteine and substituted-benzonitriles via a novel metal- and catalyst-free method. The structures of the title compounds were confirmed mainly by NMR spectral data analysis. Antibacterial activity assays showed that the compounds (S)-2-(2′-hydroxyphenyl)-4-hydroxy-methyl- 4,5-dihydrothiazole (7h) and (R)-2-(2′-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydro-thiazole (7h′) exhibited significant inhibition against Ralstonia solanacearum, Pseudomonas syringae pv. actinidiae, Bacillus subtilis and Bacillus cereus, with minimum inhibitory concentrations (MICs) ranging from 3.91 to 31.24 μg·mL−1. The effect of substituents showed that not only electron-withdrawing groups, but also electron-donating groups could abolish the antibacterial activities unless a 2′-hydroxy group was introduced on the 2-aryl substituent of the 4,5-dihydrothiazole analogues. The results of scanning electron microscope (SEM) and fatty acid exposure experiments indicated that these antibacterial compounds influence fatty acid synthesis in the tested bacteria.

  通过一种新型的无金属和催化剂方法，设计并合成了 60 个 2-芳基-4,5-二氢噻唑类化合物，其中半胱氨酸和取代苯腈类化合物的产率为 64% 至 89%。标题化合物的结构主要通过核磁共振光谱数据分析得到了证实。抗菌活性测定结果表明，(S)-2-(2′-羟基苯基)-4-羟甲基-4,5-二氢噻唑（7h）和(R)-2-(2′-羟基苯基)-4-羟甲基-4,5-二氢噻唑（7h′）化合物对茄属拉氏菌（Ralstonia solanacearum）、丁香假单胞菌（Pseudomonas syringae pv.最低抑菌浓度为 3.91 μg-mL-1 至 31.24 μg-mL-1。取代基的影响表明，不仅取电子基团会削弱抗菌活性，而且供电子基团也会削弱抗菌活性，除非在 4,5-二氢噻唑类似物的 2-芳基取代基上引入 2′-羟基。扫描电子显微镜（SEM）和脂肪酸暴露实验的结果表明，这些抗菌化合物会影响受试细菌的脂肪酸合成。