4-iodo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine | 205640-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-iodo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 4-Iodo-1-phenylpyrazolo[3,4-d]pyrimidine
• CAS: 205640-06-8
• 化学式: C₁₁H₇IN₄
• 分子量: 322.108
• InChiKey: SKXAXZMFHXIIOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 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：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-iodo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine 在 indium 、 水 作用下， 反应 2.0h， 以30%的产率得到1-苯基吡唑并[3,4-d]嘧啶
  参考文献：
  名称：

  Dehalogenation and Barbier-Type Hydroxyalkylation of π-Deficient Haloheterocycles Using Indium

  摘要：

  The reaction of pi-deficient haloheterocycles with indium metal in water gave corresponding dehalogenated heterocycles. The use of diluted hydrochloric acid instead of water accelerated the reductive reactivity of indium metal. Furthermore, Barbier-type additions proceeded by reactions of alpha-iodoheterocycles with indium in the presence of pivalaldehyde.

  DOI：

  10.3987/com-08-s(f)95
• 作为产物：
  描述：

  4-羟基-1-苯基吡唑并[3,4-D]嘧啶 在 N-氯代丁二酰亚胺 、 氢碘酸 、 三苯基膦 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 4-iodo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  鏻盐在各种酰胺反应中的应用

  摘要：

  由三苯基膦和N-卤代琥珀酰亚胺制备的鏻盐1和2证明适用于酰胺化合物的转化。特别是，与磷酰卤的卤化相比，用这些试剂卤化缺电子杂芳族醇似乎是一种方便的方法。

  DOI：

  10.1002/1522-2675(20010516)84:5<1112::aid-hlca1112>3.0.co;2-8

文献信息

• The Selective Deiodination of Iodoheterocycles Using the PhSiH3 – In(OAc)3 System
  作者：Osamu Sugimoto、Ken-ichi Tanji、Minami Sugiyama

  DOI：10.3987/com-09-s(s)19

  日期：——

  Nitrogen-containing pi-deficient heterocyclic iodides such as iodoquinolines or iodopyridines were deiodinated by treatment with phenylsilane catalyzed by indium acetate to give the corresponding deiodinated heterocycles at ambient temperature.
• Chemistry of Heteroaryltriphenylphosphonium Iodides: Preparation from Iodoheteroaromatics and Elimination of the Phosphonium Iodide Group Using Basic Solvents
  作者：Osamu Sugimoto、Ken-ichi Tanji、Akihiro Sato

  DOI：10.3987/com-09-11799

  日期：——

  alpha- and gamma-lodoheteroaromatics were found to react with triphenylphosphine to give heteroaromatictriphenylphosphonium iodides in excellent yields. beta-lodoheteroaromatics, which are less reactive with triphenylphosphine compared to alpha- or gamma-compounds, were converted into the corresponding phosphonium iodides using palladium catalysts. Treatment of heteroaromatictriphenylphosphonium iodides resulted in the elimination of the phosphonium iodide group using basic solvents such as aqueous sodium hydroxide or ethanol - triethylamine.
• Indium-mediated dehalogenation of haloheteroaromatics in water
  作者：Natsumi Hirasawa、Yukiko Takahashi、Eri Fukuda、Osamu Sugimoto、Ken-ichi Tanji

  DOI：10.1016/j.tetlet.2007.12.116

  日期：2008.2

  It turned out that indium metal was applicable to the dehalogenation of aromatic halides in water. This method is facile and safe compared with the conventional methods such as Pd-C, Raney Ni, or halogen-metal exchange. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.