ethyl 5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate | 113697-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate
• 英文别名: 5-(methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester；ethyl 7-methyl-5-(4-methoxyphenyl)-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 5-(4-methoxyphenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate；5-(4-methoxyphenyl)-7-methyl-3-oxo-3,5-dihydro-2-thiazolo[2,3-a]pyrimidine-6-carboxylic acid ethyl ester；ethyl 5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate；ethyl 5-(4-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 113697-60-2
• 化学式: C₁₇H₁₈N₂O₄S
• 分子量: 346.407
• InChiKey: ZBTFIXITBSYPJD-UHFFFAOYSA-N

物化性质

• 熔点：
  205-206 °C(Solv: ethanol (64-17-5))
• 沸点：
  481.0±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以66%的产率得到ethyl 2-(hydroxyimino)-5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5-[1,3]thiazolo[3,2-]pyrimidine-6-carboxylate
  参考文献：
  名称：

  5 H-噻唑并[3,2- a]嘧啶-3（2 H）-一的亚硝化

  摘要：

  室温下，2,3-二氢-5 H-噻唑并[3,2 - a ]嘧啶-3-酮与亚硝酸钠在乙酸中的反应得到2-（羟基亚氨基）-5Н-噻唑并[3,2-一个]嘧啶3（2 Н） -酮，根据NMR数据，其作为单一异构体。通过B3LYP / 6-311 ++ G（d，p）方法进行的计算表明，羟基亚氨基衍生物的Å-异构体比Z-异构体的亲和力高15.7 kJ / mol 。

  DOI：

  10.1007/s10593-015-1710-9
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 cerium(III) chloride heptahydrate 、 sodium acetate 作用下， 以 乙醇 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 11.0h， 生成 ethyl 5-(4-methoxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo<3,2-a>pyrimidine-6-carboxylate
  参考文献：
  名称：

  Biological evaluation of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives targeting the YycG histidine kinase

  摘要：

  With an intention to potent inhibitors of YycG histidine kinase, a series of halogenated thiazolo[3,2-a]pyrimidin-3-one carboxylic acid derivatives were synthesized and evaluated for their antibacterial, antibiofilm and hemolytic activities. The majority of the compounds showed good activity against Staphylococcus epidermidis and Staphylococcus aureus, with MIC values of 1.56-6.25 mu M, simultaneously presented promising antiobifilm activity against S. epidermidis ATCC35984 at 50 mu M. The test of inhibitory activity on YycG kinase suggested the antibacterial activities of these derivatives are based on inhibiting the enzyme activity of the YycG HK domain. The hemolytic activity test suggested these compounds exhibited in vitro antibacterial activity at non-hemolytic concentrations. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.096

文献信息

• Alkylation of 2-(hydroxyimino)-5H-[1,3]thiazolo[3,2-a]-pyrimidin-3(2H)-ones
  作者：E. A. Lashmanova、V. S. Larina、A. K. Shiryaev

  DOI：10.1134/s1070428017080152

  日期：2017.8

  products were obtained from ethyl 2-(hydroxyimino)-7-methyl-3-oxo-5-aryl-2,3- dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-carboxylates at the treatment with alkyl halides, dimethyl sulfate, and diazomethane. Diazomethane alkylated the initial substrate at the oxygen atom of the carbonyl group of the thiazolidine fragment, the other reagents, at the oxygen atom of the hydroxyimino group.

  从2-（羟基亚氨基）-7-甲基-3-氧代-5-芳基-2,3-二氢-5 H- [1,3]噻唑洛[3,2-a]嘧啶-6-获得烷基化产物。在用卤代烷，硫酸二甲酯和重氮甲烷处理的过程中羧酸盐。重氮甲烷在噻唑烷片段的羰基的氧原子处将起始底物烷基化，其他试剂在羟基亚氨基的氧原子处烷基化。
• Synthesis of some new derivatives of thiazolopyrimidines and hydrolysis of its arylidene derivative
  作者：H NAGARAJAIAH、IMTIYAZ AHMED M KHAZI、NOOR SHAHINA BEGUM

  DOI：10.1007/s12039-015-0797-y

  日期：2015.3

  procedure for the synthesis of arylidene derivatives of thiazolopyrimidine is described. The main advantages of this protocol is that it is economical, short reaction time, commonly available chemicals, and ease of isolation of products. In addition, a new series of thiazole-fused pyrimidines were synthesized and hydrolysis of one of its arylidene derivative studied. All the compounds were characterized

  描述了一种新的乙酸铵辅助，方便和有效的合成噻唑并嘧啶的亚芳基衍生物的方法。该方案的主要优点是经济，反应时间短，常用化学品以及易于分离的产物。另外，合成了一系列新的噻唑稠合的嘧啶，并研究了其亚芳基衍生物的水解。所有化合物均通过分析和光谱法表征。此外，通过X射线晶体结构分析确认了水解产物和其他两种化合物的结构。晶体结构通过分子间CH稳定。。.O，CH。。.N，CH。。。π和π。。。π弱互动。为了测试它们的抗菌和抗真菌活性，对化合物进行了抗菌筛选。 描述了一种新的乙酸铵辅助，方便，有效的合成噻唑并嘧啶的亚芳基衍生物的方法。此外，合成了一系列新的噻唑基融合的嘧啶，并研究了亚芳基衍生物的水解。
• Rearrangement of thiazolo[3,2-a]pyrimidines into triazolo[4,3-a]pyrimidines induced by C=N bond reduction
  作者：Eugenia A. Lashmanova、Artem S. Agarkov、Victor B. Rybakov、Andrey K. Shiryaev

  DOI：10.1007/s10593-019-02604-4

  日期：2019.12

  Triazolo[4,3-a]pyrimidines were prepared by the reduction of 5,6,7-trisubstituted 2-(arylhydrazinylidene)-5H-[1,3]thiazolo[3,2-a]- pyrimidin-3(2H)-ones with NaBH4 in the presence of V2O5 at room temperature. The structure of ethyl 3-(hydroxymethyl)- 5-(4-methoxyphenyl)-7-methyl-1-phenyl-1,5-dihydro[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylate was proven by the single crystal X-ray diffraction data

  通过还原5,6,7-三取代的2-（芳基肼基亚基）-5 H- [1,3]噻唑并[3,2 - a ]-嘧啶-3（2 ）制备三唑并[4,3- a ]嘧啶在室温下在V 2 O 5存在下用NaBH 4形成H）一。乙基3-（羟甲基）-5-（4-甲氧基苯基）-7-甲基-1-苯基-1,5-二氢[1,2,4]三唑并[4,3 - a ]嘧啶-6-的结构通过单晶X射线衍射数据证明了羧酸盐。讨论了包括过渡笼结构在内的反应机理。
• Synthesis of thiazolo[3,2-a]pyrimidines based on 4-aryl-substituted 3,4-dihydro-pyrimidine(1H)-2-thiones and the crystal structure of ethyl 5-(2,4-dimethoxyphenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo-[3,2-a]pyrimidine-6-carboxylate
  作者：I. V. Kulakov、O. A. Nurkenov、D. M. Turdybekov、G. M. Issabaeva、A. S. Mahmutova、K. M. Turdybekov

  DOI：10.1007/s10593-009-0346-z

  日期：2009.7

  Thiazolo[3,2-a]pyrimidines were obtained in good yield by the reaction of 4-aryl-substituted 3,4-dihydropyrimidine(1H)-2-thiones and methyl chloroacetate in boiling toluene. Their structures were shown by 1H NMR spectroscopy and X-ray crystallography.

  通过使4-芳基取代的3，4-二氢嘧啶（1H）-2-硫酮与氯乙酸甲酯在沸腾的甲苯中反应，以高收率获得噻唑并[3，2- a ]嘧啶。它们的结构通过1 H NMR光谱和X射线晶体学显示。
• A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
  作者：Murugan Sathishkumar、Sangaraiah Nagarajan、Poovan Shanmugavelan、Murugan Dinesh、Alagusundaram Ponnuswamy

  DOI：10.3762/bjoc.9.78

  日期：——

  A rapid and efficient one pot solvent/scavenger-free protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2-phenylcyclohex-2-enylimino)thiazolidin-4-one as the sole product in good yield. The selectivities observed have been rationalized based on the relative magnitude of the allylic strains developed during the course of the reaction. This is the first report wherein the impact of allylic strains in directing the regiocyclization has been noted.

  已经开发了一种快速高效的单锅无溶剂/清除剂合成2-亚氨基噻唑啉-4-酮的方案。有趣的是，区域/立体选择性合成只产生区异构体(Z)-3-烷基/芳基-2-(2-苯基环己-2-烯基亚氨基)噻唑啉-4-酮，收率良好。观察到的选择性是基于反应过程中产生的联烯应变相对大小的合理化。这是第一篇注意到联烯应变对定向区域环化的影响的报告。