1-phenyl-4-(toluene-4-sulfonyl)-1H-pyrazolo[3,4-d]pyrimidine | 66421-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-4-(toluene-4-sulfonyl)-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 4-(4-Methylphenyl)sulfonyl-1-phenylpyrazolo[3,4-d]pyrimidine
• CAS: 66421-39-4
• 化学式: C₁₈H₁₄N₄O₂S
• 分子量: 350.401
• InChiKey: JFNWMXMKUWNMCY-UHFFFAOYSA-N

物化性质

• 沸点：
  523.4±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-phenyl-4-(toluene-4-sulfonyl)-1H-pyrazolo[3,4-d]pyrimidine 、 苯甲醛 在 potassium cyanide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以74%的产率得到phenyl-(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone
  参考文献：
  名称：

  Several Approaches to Cyanide Ion-catalyzed Synthesis of 4-Aroyl-1-phenyl-1H-pyrazolo-[3,4-d]pyrimidines

  摘要：

  4-Aroyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidines (5) were formed in low yields by reaction of 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (4) with arenecarbaldehydes (3) in the presence of potassium cyanide. Similar reaction of 4-tosyl-1-phenyl-1H-pyrazolo [3,4-d]pyrimidine (9) with 3 gave the ketones (5) in higher yields (60-74%). In the presence of catalytic amounts of both sodium p-toluenesulfinate (10) and potassium cyanide, the reaction of 4 with 3 gave the ketones (5) in good yields.

  DOI：

  10.3987/com-97-s(n)53
• 作为产物：
  描述：

  4-氯-1-苯基-1H-吡唑并[3,4-d]嘧啶 在 sodium hydride 、 硫脲 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-phenyl-4-(toluene-4-sulfonyl)-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide

  摘要：

  Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).

  DOI：

  10.3987/com-97-7740

文献信息

• US4182878A
  申请人：——

  公开号：US4182878A

  公开（公告）日：1980-01-08
• Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide
  作者：Akira Miyashita、Izuru Nagasaki、Akiko Kawano、Yumiko Suzuki、Ken-ichi Iwamoto、Takeo Higashino

  DOI：10.3987/com-97-7740

  日期：——

  Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).
• Several Approaches to Cyanide Ion-catalyzed Synthesis of 4-Aroyl-1-phenyl-1H-pyrazolo-[3,4-d]pyrimidines
  作者：Akira Miyashita、Yumiko Suzuki、Kiyono Ohta、Ken-ichi Iwamoto、Takeo Higashino

  DOI：10.3987/com-97-s(n)53

  日期：——

  4-Aroyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidines (5) were formed in low yields by reaction of 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (4) with arenecarbaldehydes (3) in the presence of potassium cyanide. Similar reaction of 4-tosyl-1-phenyl-1H-pyrazolo [3,4-d]pyrimidine (9) with 3 gave the ketones (5) in higher yields (60-74%). In the presence of catalytic amounts of both sodium p-toluenesulfinate (10) and potassium cyanide, the reaction of 4 with 3 gave the ketones (5) in good yields.