3-Allyl-2,3-dihydrothiazolo<4,5-d>pyrimidin-2,7-dithion | 130089-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-Allyl-2,3-dihydrothiazolo<4,5-d>pyrimidin-2,7-dithion
• 英文别名: 3-allyl-6H-thiazolo[4,5-d]pyrimidine-2,7-dithione；3-prop-2-enyl-4H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dithione
• CAS: 130089-92-8
• 化学式: C₈H₇N₃S₃
• 分子量: 241.362
• InChiKey: SNFAFVQLTMGBOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  342.9±52.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Allyl-2,3-dihydrothiazolo<4,5-d>pyrimidin-2,7-dithion 以80%的产率得到
  参考文献：
  名称：

  Gewald K., Hain U., Schindler R., Gruner M., Monatsh. Chem, 125 (1994) N 10, S 1129-1143

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Allyl-2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-one 在 tetraphosphorus decasulfide 作用下， 以 xylene 为溶剂， 反应 5.0h， 以73%的产率得到3-Allyl-2,3-dihydrothiazolo<4,5-d>pyrimidin-2,7-dithion
  参考文献：
  名称：

  Condensed thiazoles, II: Synthesis of 7-substituted thiazolo[4,5-d]pyrimidines as possible anti-HIV, anticancer, and antimicrobial agents

  摘要：

  Some 3-substituted 2-thioxothiazolo[4,5-d]pyrimidin-7(6H)-ones (2a, b; 4) have been synthesized and converted to their 7-chloro (3, 5), 7-diethanolamino (6a,b), 7-bis(2-chloroethyl)amino (7), 7-azido (8), 7-amino (9), 7-hydrazino (10), 7-mercapto (11a, b), and 7-methylthio (12) derivatives. These compounds were evaluated for their in vitro antimicrobial, anti-HIV, and anticancer activities.

  DOI：

  10.1007/bf00844697

文献信息

• Gewald, K.; Schindler, R., Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 2, p. 223 - 228
  作者：Gewald, K.、Schindler, R.

  DOI：——

  日期：——
• Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.
  作者：K. Gewald、U. Hain、R. Schindler、M. Gruner

  DOI：10.1007/bf00811521

  日期：1994.10

  6-Amino-thiazolo[4,5-c]isothiazole derivatives 4 are obtained by addition of hydrogen sulfide to the 4-Amino-thiazoline-5-carbonitrile 2 followed by cyclooxidation of the intermediate thioamides 3. In the presence of sodium sulfite the hydrolysis of the 4-amino-2-methylthio-thiazolium salts 5 derived from the title compounds 1 yields the 4-amino-thiazolin-2-ones 6. By their further hydrolysis the 2,4-dioxo-thiazolidin-5-carboxamides 8 are formed. The 2-oxo-and 2-thioxo-thiazolo [4,5-d]pyrimidin-7-ones and -thiones available from 1 undergo ring opening by hydrolysis to give the substituted 4-amino-6-oxo- and 4-amino-6-thioxo-pyrimidine-5-thiols 15a-h and 13i-e. They have been isolated as their disulfides 14 or 5-alkyl derivatives i.e. the substituted 4-amino-5-alkylthiopyrimidin-6-ones and -thiones 16. In analogy, the intermediate 6-amino-7-oxo-thiazolo[4,5-d] pyrimidin-2-thione 18 and the 7-amino-thiazolo[4,5-d]-pyrimidin-2-thione 24 derived from 1 react by ring cleavage to yield the 1,4- and 4,6-diamino-pyrimidin-5-thiole derivatives 22 and 27, respectively, isolated as their disulfides or alkylthio-derivatives. From the pyrimidine 16b the pyrimido[5,4-b]1,4-thiazine derivative 18 can be obtained.