1-Hydrazino-3-thioxo-5,6,7,8-tetrahydro-3H-isothiochromene-4-carbonitrile | 180746-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 1-Hydrazino-3-thioxo-5,6,7,8-tetrahydro-3H-isothiochromene-4-carbonitrile
• CAS: 180746-38-7
• 化学式: C₁₀H₁₁N₃S₂
• 分子量: 237.349
• InChiKey: PLFSFWQHJTYFTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.84
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-Hydrazino-3-thioxo-5,6,7,8-tetrahydro-3H-isothiochromene-4-carbonitrile 、 碘甲烷 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以52%的产率得到4,5-Butano-6-hydrazono-2-methylthio-6H-thiopyran-3-carbonitril
  参考文献：
  名称：

  Darstellung und Reaktionen von 2-Mercapto-6-thioxo-thiopyran-3-carbons�ure-Derivaten

  摘要：

  6-Amino-thiopyran-2-thiones (1) react with dihydrogen sulfide in the presence of pyridine and triethyl amine to yield 6-thioxo-thiopyran-2-thiolates (2). Methylation of 2 gives the methylthio compounds 3 and 4. Further methylation of 3a and 4a yields the thiapyrylium salt (7). The reaction of 2-imino-thiopyran (6) with carbon disulfide represents another route to the 6-methylthio-thiopyran-2-thione (4a). The 2-methylthio-thiopyran-6-thione (3a) undergoes substitution of the methylthio group with amines to 8 or reacts with phenylhydrazine to phenylhydrazono-thiopyrane (9c). 6-Thioxo-thiophen-2-thiolates (2a,b) react with hydrazine hydrate to give hydrazono-thiopyranes (10a,b) which can be S-methylated. On the contrary 2c gives with hydrazine hydrate under ring transformation the pyridine-2-thiolate (11). N,S-Acetals (12) and 1,3,4-thiadiazoles (15), which give rise to new pyridine derivatives (14) and (17), can be obtained from 1-Amino-pyridin-2-thiolate (11).

  DOI：

  10.1002/prac.19963380198
• 作为产物：
  描述：

  1H-2-苯并硫代吡喃-4-甲腈,5,6,7,8-四氢-3-氨基-1-硫代- 在 硫化氢 、 一水合肼 、 三乙胺 作用下， 反应 192.0h， 生成 1-Hydrazino-3-thioxo-5,6,7,8-tetrahydro-3H-isothiochromene-4-carbonitrile
  参考文献：
  名称：

  Darstellung und Reaktionen von 2-Mercapto-6-thioxo-thiopyran-3-carbons�ure-Derivaten

  摘要：

  6-Amino-thiopyran-2-thiones (1) react with dihydrogen sulfide in the presence of pyridine and triethyl amine to yield 6-thioxo-thiopyran-2-thiolates (2). Methylation of 2 gives the methylthio compounds 3 and 4. Further methylation of 3a and 4a yields the thiapyrylium salt (7). The reaction of 2-imino-thiopyran (6) with carbon disulfide represents another route to the 6-methylthio-thiopyran-2-thione (4a). The 2-methylthio-thiopyran-6-thione (3a) undergoes substitution of the methylthio group with amines to 8 or reacts with phenylhydrazine to phenylhydrazono-thiopyrane (9c). 6-Thioxo-thiophen-2-thiolates (2a,b) react with hydrazine hydrate to give hydrazono-thiopyranes (10a,b) which can be S-methylated. On the contrary 2c gives with hydrazine hydrate under ring transformation the pyridine-2-thiolate (11). N,S-Acetals (12) and 1,3,4-thiadiazoles (15), which give rise to new pyridine derivatives (14) and (17), can be obtained from 1-Amino-pyridin-2-thiolate (11).

  DOI：

  10.1002/prac.19963380198