5-[[4-oxo-6-(prop-2-enylamino)-1H-pyrimidin-5-yl]disulfanyl]-6-(prop-2-enylamino)-1H-pyrimidin-4-one | 159897-69-5

• 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: 5-[[4-oxo-6-(prop-2-enylamino)-1H-pyrimidin-5-yl]disulfanyl]-6-(prop-2-enylamino)-1H-pyrimidin-4-one
• CAS: 159897-69-5
• 化学式: C₁₄H₁₆N₆O₂S₂
• 分子量: 364.452
• InChiKey: YRFPKPDWJBRDCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  115.56
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-[[4-oxo-6-(prop-2-enylamino)-1H-pyrimidin-5-yl]disulfanyl]-6-(prop-2-enylamino)-1H-pyrimidin-4-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 sodium dithionite 作用下， 生成 6-Allylamino-5-methylsulfanyl-3H-pyrimidin-4-one
  参考文献：
  名称：

  Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.

  摘要：

  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.

  DOI：

  10.1007/bf00811521
• 作为产物：
  描述：

  3-Allyl-3H,6H-thiazolo[4,5-d]pyrimidine-2,7-dione 在 sodium hydroxide 、 air 作用下， 反应 20.0h， 生成 5-[[4-oxo-6-(prop-2-enylamino)-1H-pyrimidin-5-yl]disulfanyl]-6-(prop-2-enylamino)-1H-pyrimidin-4-one
  参考文献：
  名称：

  Zur Chemie der 4-Amino-thiazolin-2-thione, 2. Mitt.

  摘要：

  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.

  DOI：

  10.1007/bf00811521

文献信息

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

  DOI：——

  日期：——