5-(2-chlorophenyl)-6-(ethoxycarbonyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin | 313276-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-chlorophenyl)-6-(ethoxycarbonyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin
• 英文别名: ethyl 5-(2-chlorophenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS: 313276-45-8
• 化学式: C₁₆H₁₅ClN₂O₃S
• 分子量: 350.826
• InChiKey: DAHNASBFKGPBQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-chlorophenyl)-6-(ethoxycarbonyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以86%的产率得到ethyl 5-(2-chlorophenyl)-2-hydroxyimino-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-(2-氯苯基)-1,2,3,4-四氢-6-甲基-2-硫代-5-嘧啶羧酸乙酯 、 氯乙酸乙酯 在 氨 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以61%的产率得到5-(2-chlorophenyl)-6-(ethoxycarbonyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin
  参考文献：
  名称：

  Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent

  摘要：

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.014

文献信息

• Pathak, Arun; Narayanaswamy, Venugopala Katharigatta; Joshi, Aakanksha, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 273 - 276
  作者：Pathak, Arun、Narayanaswamy, Venugopala Katharigatta、Joshi, Aakanksha、Rao, Gopal Krishna、Devi, Kalpana

  DOI：——

  日期：——
• Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent
  作者：Eugenia A. Lashmanova、Anastasiya I. Kirdyashkina、Pavel A. Slepukhin、Andrey K. Shiryaev

  DOI：10.1016/j.tetlet.2018.02.014

  日期：2018.3

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.
• Nitrosation of 5H-thiazolo[3,2-a]pyrimidin-3(2H)-ones
  作者：Evgenia A. Lashmanova、Andrey K. Shiryaev

  DOI：10.1007/s10593-015-1710-9

  日期：2015.4

  The reaction of 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-ones with sodium nitrite in acetic acid at room temperature gave 2-(hydroxyimino)-5Н-thiazolo[3,2-a]pyrimidin-3(2Н)-ones, which exist as a single isomer according to NMR data. Calculations by the B3LYP/6-311++G(d,p) method indicated that the Е-isomer of hydroxyimino derivative was favored by 15.7 kJ/mol over the Z-isomer.

  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 。