1-苯基吡唑并[3,4-d]嘧啶-4-腈 | 65143-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-苯基吡唑并[3,4-d]嘧啶-4-腈
• 英文名称: 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile
• 英文别名: 1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-carbonitrile；1-phenylpyrazolo[3,4-d]pyrimidine-4-carbonitrile
• CAS: 65143-08-0
• 化学式: C₁₂H₇N₅
• 分子量: 221.221
• InChiKey: LGGKAYYYLDMGJD-UHFFFAOYSA-N

物化性质

• 熔点：
  190.5-191.5 °C(Solv: benzene (71-43-2))
• 沸点：
  365.2±35.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苯基吡唑并[3,4-d]嘧啶-4-腈 生成 4-羟基-1-苯基吡唑并[3,4-D]嘧啶
  参考文献：
  名称：

  HAYASHI EISAKU; HIGASHINO TAKEO; SUZUKI SHIN-ICHI, HETEROCYCLES, 1979, 12, NO 1, 202

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-1-苯基吡唑并[3,4-D]嘧啶 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-苯基吡唑并[3,4-d]嘧啶-4-腈
  参考文献：
  名称：

  Tanji, Ken-ichi; Yokoi, Takeshi; Sugimoto, Osamu, Heterocycles, 2003, vol. 60, # 2, p. 413 - 418

  摘要：

  DOI：

文献信息

• Ring transformation of condensed pyrimidines by enamines and ynamines. Formation of condensed pyridines and condensed diazocines.
  作者：Akira MIYASHITA、Naokata TAIDO、Susumu SATO、Ken-ichi YAMAMOTO、Hitoshi ISHIDA、Takeo HIGASHINO

  DOI：10.1248/cpb.39.282

  日期：——

  A [4+2]-cycloaddition of quinazoline (2) and the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidine 4 with enamines 1a-e resulted in ring transformation into the quinolines, 3a and 3c, and the 3H-1, 2, 3-triazolo[4, 5-b]pyridines, 5a-e, respectively. Similarly, the ynamine 13a cycloadded to 2 and its 4-cyano derivative 6, giving the quinolines, 14a and 14b, respectively.On the other hand, the 3H-1, 2, 3-triazolo[4, 5-d]pyrimidines 4, 15, 8, 16, 17, 18, and 19 underwent [2+2]-cycloaddition with the ynamine 13a, resulting in ring transformation into the corresponding 3H-1, 2, 3-triazolo[4, 5-d]-[1, 3]diazocines 21a-27. The 7-methoxy derivative 20, the 4-methoxy- and 4-cyano-1H-pyrazolo[3, 4-d]pyrimidines, 30 and 31, and the 6-cyano-9H-purine 36 also underwent [2+2]-cycloaddition with 13a to give the corresponding 3H-1, 2-3-triazolo[4, 5-b][1, 5]diazocine 28, 1H-pyrazolo[3, 4-b][1, 5]diazocines, 32 and 33, and 3H-imidazo[4, 5-b]-[1, 5]diazocine 37, respectively.The structures of the 1, 3- and 1, 5-diazocines, 21a and 28, were determined by X-ray crystallography.

  喹唑啉（2）和3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4）与烯胺（1a-e）进行[4+2]环加成反应，导致环转化为喹啉（3a和3c）和相应的3H-1, 2, 3-三氮杂[4, 5-b]吡啶（5a-e）。类似地，烯氨（13a）与2及其4-氰基衍生物6进行环加成，分别生成喹啉（14a和14b）。另一方面，3H-1, 2, 3-三氮杂[4, 5-d]嘧啶（4、15、8、16、17、18和19）与烯氨（13a）发生[2+2]环加成反应，导致环转化为相应的3H-1, 2, 3-三氮杂[4, 5-d]-[1, 3]二氮环（21a-27）。7-甲氧基衍生物20、4-甲氧基和4-氰基的1H-吡唑[3, 4-d]嘧啶（30和31）以及6-氰基-9H-嘌呤（36）也与13a发生[2+2]环加成，分别生成相应的3H-1, 2-3-三氮杂[4, 5-b][1, 5]二氮环（28）、1H-吡唑[3, 4-b][1, 5]二氮环（32和33）和3H-咪唑[4, 5-b]-[1, 5]二氮环（37）。1, 3-和1, 5-二氮环（21a和28）的结构通过X射线晶体学确定。
• Higashino, Takeo; Sato, Susumu; Miyashita, Akira, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 11, p. 4569 - 4576
  作者：Higashino, Takeo、Sato, Susumu、Miyashita, Akira、Katori, Tatsuhiko

  DOI：——

  日期：——
• 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.
• Hagishino, Takeo; Sato, Susumu; Miyashita, Akira, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 10, p. 4078 - 4086
  作者：Hagishino, Takeo、Sato, Susumu、Miyashita, Akira、Katori, Tatsuhiko

  DOI：——

  日期：——
• Preparation of Heteroarenecarbonitriles by Reaction of Haloheteroarenes with Potassium Cyanide Catalyzed by Sodium p-Toluenesulfinate
  作者：Akira Miyashita、Yumiko Suzuki、Kiyono Ohta、Takeo Higashino

  DOI：10.3987/com-94-s(b)38

  日期：——

  Several heteroarenecarbonitriles were prepared by reaction of haloheteroarenes with potassium cyanide catalyzed by sodium p-toluenesulfinate (1) or sodium methanesulfinate (2). In the reaction pathway, the cyanation proceeds through the formation of the sulfonylheteroarenes.