6-allylsulfanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one | 850911-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-allylsulfanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
• 英文别名: 1-Phenyl-6-(prop-2-EN-1-ylsulfanyl)-1H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-one；1-phenyl-6-prop-2-enylsulfanyl-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 850911-53-4
• 化学式: C₁₄H₁₂N₄OS
• mdl: MFCD03667623
• 分子量: 284.341
• InChiKey: HCHKQILQJJXOAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-allylsulfanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 在 硫酸 作用下， 反应 14.0h， 以92%的产率得到8-methyl-1-phenyl-1,4,7,8-tetrahydropyrazolo[4,3-e][1,3]thiazolo[3,2-a]pyrimidin-4-one
  参考文献：
  名称：

  Electrophilic heterocyclization of 6-alken(yn)ylsulfanyl-pyrazolo[3,4-d]pyrimidin-4(5H)-ones

  摘要：

  6-Allylsulfanyl-1-arylpyrazolo[3,4-d]pyrimidin-4(5H)-ones react with iodine and sulfuric acid to give angular pyrazolothiazolopyrimidine derivatives. The reaction of 6-(prop-2-yn-1-ylsulfanyl)-1-(4-tolyl)-pyrazolo[3,4-d]pyrimidin-4(5H)-one with sulfuric acid gives angularly fused pyrazolo[4,3-e][1,3]thiazolo-[3,2-a]pyrimidin-4-one, whereas in the reaction with sodium methoxide linearly fused pyrazolo[3,4-d][1,3]-thiazolo[3,2-a]pyrimidin-4-one was formed. Linearly fused pyrazolo[3',4':4,5]pyrimido[2,1-b][1,3]thiazole derivatives were also obtained by reaction of 1-aryl-6-(3-phenylprop-2-en-1-ylsulfanyl)pyrazolo[3,4-d]pyrimidin-4(5H)-ones with sulfuric acid.

  DOI：

  10.1134/s1070428008090194
• 作为产物：
  描述：

  4H-吡唑并[3,4-d]嘧啶-4-酮,1,5,6,7-四氢-1-苯基-6-硫代- 、 3-溴丙烯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以77%的产率得到6-allylsulfanyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  Electrophilic heterocyclization of 6-alken(yn)ylsulfanyl-pyrazolo[3,4-d]pyrimidin-4(5H)-ones

  摘要：

  6-Allylsulfanyl-1-arylpyrazolo[3,4-d]pyrimidin-4(5H)-ones react with iodine and sulfuric acid to give angular pyrazolothiazolopyrimidine derivatives. The reaction of 6-(prop-2-yn-1-ylsulfanyl)-1-(4-tolyl)-pyrazolo[3,4-d]pyrimidin-4(5H)-one with sulfuric acid gives angularly fused pyrazolo[4,3-e][1,3]thiazolo-[3,2-a]pyrimidin-4-one, whereas in the reaction with sodium methoxide linearly fused pyrazolo[3,4-d][1,3]-thiazolo[3,2-a]pyrimidin-4-one was formed. Linearly fused pyrazolo[3',4':4,5]pyrimido[2,1-b][1,3]thiazole derivatives were also obtained by reaction of 1-aryl-6-(3-phenylprop-2-en-1-ylsulfanyl)pyrazolo[3,4-d]pyrimidin-4(5H)-ones with sulfuric acid.

  DOI：

  10.1134/s1070428008090194

文献信息

• Cyclofunctionalization of 6-alkenylsulfanylpyrazolo[3,4-d]-pyrimidin-4(5H)-ones with arenesulfenyl chlorides
  作者：A. I. Vas’kevich、A. V. Bentya、V. I. Staninets

  DOI：10.1134/s1070428009120161

  日期：2009.12

  Reactions of 6-allylsulfanylpyrazolo[3,4-d]pyrimidin-4(5H)-one with arenesulfenyl chlorides in chloroform gave products of addition of the latter at the exocyclic double bond, while analogous reactions in acetic acid in the presence of LiClO4 were accompanied by intramolecular electrophilic cyclization involving the N7 atom. 6-Cinnamylsulfanylpyrazolo[3,4-d]pyrimidin-4(5H)-one reacted with arenesulfenyl chlorides

  6-烯丙基硫烷基吡唑并[3,4- d ]嘧啶-4（5 H）-one与亚芳基磺酰氯在氯仿中的反应得到后者在环外双键上的加成产物，而类似的反应是在乙酸中以LiClO存在4个伴随有涉及N 7原子的分子内亲电环化。6-肉桂基硫烷基吡唑并[3,4- d ]嘧啶-4（5 H）-在没有电解质的情况下，与乙酸亚芳基氯在乙酸中反应生成稠合的吡唑并[4'，3'：5,6]嘧啶并[2， 1- b ] [1,3]噻嗪衍生物。将大体积的苯基引入吡唑并[3,4- d]的位置1由于同时形成无环加成产物，]嘧啶体系降低了在N 7处相应分子内环化产物的产率。土井