5-Iodo-1,3-dimethylpyrazole-4-carbonamide | 133053-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Iodo-1,3-dimethylpyrazole-4-carbonamide
• 英文别名: 5-iodo-1,3-dimethyl-1H-pyrazole-4-carboxamide；5-iodo-1,3-dimethylpyrazole-4-carboxamide
• CAS: 133053-60-8
• 化学式: C₆H₈IN₃O
• 分子量: 265.054
• InChiKey: CRZJLOQCQXRSSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.91
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-Iodo-1,3-dimethylpyrazole-4-carbonamide 在 bis-triphenylphosphine-palladium(II) chloride 氢氧化钾 、 copper(l) iodide 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 1,3-Dimethyl-6-phenoxymethyl-1,5-dihydro-pyrazolo[4,3-c]pyridin-4-one
  参考文献：
  名称：

  Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides

  摘要：

  Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or five-membered lactam ring. The formation of a gamma-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.

  DOI：

  10.1007/bf00958258
• 作为产物：
  描述：

  1,3-二甲基-1H-吡唑-4-羧酸 在 氯化亚砜 、 硫酸 、 氨 、 碘 、 碘酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 5-Iodo-1,3-dimethylpyrazole-4-carbonamide
  参考文献：
  名称：

  Cyclization of vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides

  摘要：

  Vicinal acetylenic derivatives of pyrazolecarbonamides and benzamides cyclize in alcoholic solution in the presence of KOH with closure of the six- or five-membered lactam ring. The formation of a gamma-lactam (from o-phenylethynylbenzamide) has been noted for the first time. Condensation of vicinal iodopyrazolecarbonamides with copper phenylacetylide gives the pyrazolylacetylenes without concurrent intramolecular cyclization of the product to give the cyclopentadienone ring. We have been unable to repeat the reported similar cyclocondensation of o-iodobenzamide to 3-amino-2-phenylindenone.

  DOI：

  10.1007/bf00958258

文献信息

• Functionalized buta-1,3-diynyl- N -methylpyrazoles by sequential “diacetylene zipper” and Sonogashira coupling reactions
  作者：Anastasiya I. Govdi、Alexandra E. Kulyashova、Sergey F. Vasilevsky、Irina A. Balova

  DOI：10.1016/j.tetlet.2017.01.032

  日期：2017.2

  A reaction sequence consisting of the “Diacetylene zipper” of buta-1,3-diynes from internal to terminal isomers, followed by Sonogashira cross-coupling with 3-,4- or 5-iodopyrazoles, was investigated as a new approach to buta-1,3-diynyl-N-methylpyrazoles. Various pyrazoles bearing alkyl and hydroxyalkyl containing buta-1,3-diyne substituents in the 3-,4- or 5-position and functional groups at the neighboring

  研究了由内部异构体到末端异构体的Buta-1,3-diynes的“二乙炔拉链”，然后将Sonogashira与3-，4-或5-碘吡唑交叉偶联的反应顺序，是一种新的Buta- 1,3-二炔基-N-甲基吡唑。得到了各种带有在3-，4-或5-位上含有buta-1，3-diyne取代基和在环的相邻位置上具有官能团的烷基和羟烷基的吡唑。
• VASILEVSKIJ, S. F.;SHVARTSBERG, M. S., IZV. AN CCCP. CEP. XIM.,(1990) N, S. 2089-2093
  作者：VASILEVSKIJ, S. F.、SHVARTSBERG, M. S.

  DOI：——

  日期：——