Methanone, phenyl(3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-yl)- | 99934-01-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanone, phenyl(3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-yl)-
• 英文别名: phenyl-(3-phenyltriazolo[4,5-d]pyrimidin-7-yl)methanone
• CAS: 99934-01-7
• 化学式: C₁₇H₁₁N₅O
• 分子量: 301.307
• InChiKey: MTWMTEHBQGSEMF-UHFFFAOYSA-N

物化性质

• 熔点：
  141 °C
• 沸点：
  522.4±53.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methanone, phenyl(3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-yl)- 在 potassium cyanide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-phenyl-3H-[1,2,3]triazolo-[4,5-d]pyrimidine
  参考文献：
  名称：

  Carbon-Carbon Bond Cleavage of .ALPHA.-Hydroxybenzylheteroarenes Catalyzed by Cyanide Ion: Retro-Benzoin Condensation Affords Ketones and Heteroarenes and Benzyl Migration Affords Benzylheteroarenes and Arenecarbaldehydes.

  摘要：

  4-(α-苄基-α-羟基苄基)喹唑啉(4a)在氰离子催化下经历逆苯偶姻缩合反应，生成脱氧苯偶姻(2a)和喹唑啉(5a)。同样，多个含氮杂环芳烃(4, 9, 12, 16-19)在其氮原子的α位上具有α-羟基苄基的结构，也经历逆苯偶姻型缩合反应，生成了酮(2)和杂环芳烃(5)。然而，具有α-苄基-α-羟基苄基结构的吡唑嘧啶(13, 14, 15)在类似的反应中引发了苄基迁移，生成了苄基吡唑嘧啶(8)和芳烃羰醛(3)。四丁基铵氰(11, Bu4NCN)比KCN(10)更有效地作为氰离子的供体。逆苯偶姻缩合反应被应用于从2-氯-4-芳酰基喹唑啉(34)合成2-取代喹唑啉(38)，使用芳酰基作为保护和电子 withdrawing 基团。

  DOI：

  10.1248/cpb.46.199
• 作为产物：
  描述：

  7-chloro-3-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine 在 正丁基锂 、 四甲基乙二胺 、 sodium iodide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 73.5h， 生成 Methanone, phenyl(3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-yl)-
  参考文献：
  名称：

  Triazolo[4,5-d]pyrimidines. X. Halogen-Metal Exchange Reaction of 7-Halo-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidines with Butyllithium.

  摘要：

  通过在卤代甲烷中使用亚硝酸异戊酯处理，3H-1，2，3-三唑并[4，5-d]嘧啶环上位于 7 位的氨基被转化为卤素原子，产率令人满意。在 N，N，N'，N'-四甲基乙二胺存在下，7-碘-3-苯基-3H-1，2，3-三唑并[4，5-d]嘧啶（2）与丁锂发生卤金属交换反应，得到 7-硫代化合物（9）。硫代锂化合物 (9) 与亲电物顺利反应，得到相应的 7-取代化合物 (15-18)。另一方面，7-氯-3-苯基-3H-1，2，3-三唑并[4，5-d]嘧啶（1）与丁锂反应得到了环裂变产物 5-氨基-1-苯基-1H-1，2，3-三唑-4-甲腈（14）。

  DOI：

  10.1248/cpb.39.2793

文献信息

• Catalytic Action of Azolium Salts. IX. Synthesis of 6-Aroyl-9H-purines and Their Analogues by Nucleophilic Aroylation Catalyzed by Imidazolium or Benzimidazolium Salt.
  作者：Akira MIYASHITA、Yumiko SUZUKI、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.46.390

  日期：——

  In the presence of 1, 3-dimethylimidazolium iodide (1), 6-chloro-9-phenyl-9H-purine (7) and 4-chloro-5, 6-dimethylpyrrolo[2, 3-d]pyrimidines 40-42 undrwent uncleophilic aroylation with arenecarbaldehydes (5) to give the corresponding fused aroylpyrimidines 8 and 43-45. 1, 3-Dimethylbenzimidazolium iodide (2) was an effective catalyst for the similar synthesis of 7-aroyl-3-phenyl-3H-1, 2, 3-triazolo[4, 5-d]pyrimidines 16-21. In the synthesis of 4-aroyl-1H-pyrazolo[3, 4-d]pyrimidines 26-32, both azolium salts 1 and 2 were effective as catalysts. Moreover, 4-aroyl-7H-pyrrolo[2, 3-d]pyrimidines 43-45 were obtained in good yields via the 4-tosyl derivatives, in the presence of catalytic amounts of sodium p-toluenesulfinate (46) and the imidazolium salt 1. This catalytic aroylation was found to be a facile and useful method for the synthesis of 6-aroyl-9H-purines and their analogues.

  在1, 3-二甲基咪唑鎓碘化物（1）的存在下，6-氯-9-苯基-9H-嘌呤（7）和4-氯-5, 6-二甲基吡咯并[2, 3-d]嘧啶（40-42）与芳烃醛（5）发生亲核芳酰化反应，生成相应的融合芳酰嘧啶（8和43-45）。1, 3-二甲基苯并咪唑鎓碘化物（2）是合成7-酰基-3-苯基-3H-1, 2, 3-三唑并[4, 5-d]嘧啶（16-21）的有效催化剂。在合成4-酰基-1H-吡唑并[3, 4-d]嘧啶（26-32）中，咪唑盐（1和2）均表现出良好的催化效果。此外，通过4-托磺酸衍生物，在催化量的对甲苯磺酸钠（46）和咪唑盐（1）的存在下，获得了良好产率的4-酰基-7H-吡咯并[2, 3-d]嘧啶（43-45）。这种催化芳酰化反应被发现是一种简便而有效的方法，用于合成6-酰基-9H-嘌呤及其类似物。
• Synthesis and Reactivities of 1,3-Dimethyl-2-(a-hydroxybenzyl)imidazolium and 1,3-Dimethyl-2-(a-hydroxybenzyl)benzimidazolium Iodides
  作者：Akira Miyashita、Akihito Kurachi、Yoshiyuki Matsuoka、Noriko Tanabe、Yumiko Suzuki、Ken-ichi Iwamoto、Takeo Higashino

  DOI：10.3987/com-96-s40

  日期：——

  1,3-Dimethyl-2-(alpha-hydroxybenzyl)benzimidazolium iodide (3a) was synthesized from 1-methylbenzimidazole (10) through two steps involving lithiation and quaternization. Treatment of 3a with 4-chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (6) afforded 4-benzoyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (15a). 4-Benzoylquinazoline (14a) and 7-benzoyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine (16a) were given by reaction of 3a with 4-chloroquinazolin (5) and 7-chloro-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidine. (7). Treatment of 3a with benzaldehyde (9a) gave benzoin (8a). Similar results were obtained in the reactions of 1,3-dimethyl-2-(alpha-hydroxybenzyl)imidazo iodide (4a).
• 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.
• Higashino, Takeo; Takemoto, Masumi; Miyashita, Akira, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 4, p. 1395 - 1399
  作者：Higashino, Takeo、Takemoto, Masumi、Miyashita, Akira、Hayashi, Eisaku

  DOI：——

  日期：——
• HIGASHINO, TAKEO;TAKEMOTO, MASUMI;MIYASHITA, AKIRA;HAYASHI, EISAKU, CHEM. AND PHARM. BULL., 1985, 33, N 4, 1395-1399
  作者：HIGASHINO, TAKEO、TAKEMOTO, MASUMI、MIYASHITA, AKIRA、HAYASHI, EISAKU

  DOI：——

  日期：——