5-Chloro-3-(4-chlorophenyl)-1-methylpyrazole-4-carboxaldehyde | 117007-78-0

• 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-Chloro-3-(4-chlorophenyl)-1-methylpyrazole-4-carboxaldehyde
• 英文别名: 5-Chloro-3-(4-chlorophenyl)-1-methyl-1h-pyrazole-4-carboxaldehyde；5-chloro-3-(4-chlorophenyl)-1-methylpyrazole-4-carbaldehyde
• CAS: 117007-78-0
• 化学式: C₁₁H₈Cl₂N₂O
• 分子量: 255.103
• InChiKey: JHTCJVOSRZCISE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Chloro-3-(4-chlorophenyl)-1-methylpyrazole-4-carboxaldehyde 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 生成 1-(Azidomethyl)-3-(4-chlorophenyl)-4-cyanopyrazole
  参考文献：
  名称：

  5-azido-4-formylpyrazole意外的开环-闭环反应

  摘要：

  由于开环-闭环反应的结果，在与过量的叠氮化钠在二甲基亚砜（DMSO）中反应时，5-氯-4-甲酰基-1-甲基吡唑类化合物会生成1-叠氮基甲基-4-氰基吡唑类化合物。已经确定了叠氮基甲基吡唑的晶体结构。

  DOI：

  10.1039/c39880000541
• 作为产物：
  描述：

  3-(4-chlorophenyl)-1-methyl-2-pyrazolin-5-one 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以80%的产率得到5-Chloro-3-(4-chlorophenyl)-1-methylpyrazole-4-carboxaldehyde
  参考文献：
  名称：

  Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes

  摘要：

  5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3. Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields. Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields. In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.

  DOI：

  10.1021/jo00033a039

文献信息

• Microwave-Assisted Synthesis of Ethyl 1,3-Disubstituted-1,6-dihydropyrrolo[2,3-c]pyrazole-5-carboxylates
  作者：Lijun Gu、Xiangguang Li

  DOI：10.1002/jhet.1115

  日期：2013.3

  A novel series of ethyl 1,3‐disubstituted‐1,6‐dihydropyrrolo[2,3‐c]pyrazole‐5‐carboxylates can be rapidly and efficiently synthesized in excellent yields by condensing a variety of 1,3‐substituted‐4‐formyl‐5‐chloropyrazole with ethyl isocyanoacetate in the presence of 1‐methyl‐3‐butylimidazolium hydroxide under microwave irradiation. The simple experimental procedure, DMSO‐free condition, short period

  通过缩合各种1,3-取代的-4--羟基化合物，可以快速有效地合成一系列新颖的1,3-二取代的-1,6-二氢吡咯并[2,3-c]吡唑-5-羧酸乙酯。在微波辐射下，在1-甲基-3-丁基咪唑鎓氢氧化物存在下，将甲酰基-5-氯吡唑与异氰基乙酸乙酯混合。简单的实验程序，无DMSO的条件，短的转化时间和优异的收率是本方法的优势。新型化合物的结构已通过IR，1 H NMR，13 C NMR，MALDI-TOF MS和元素分析得到证实。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Nuevolution A/S

  公开号：EP2558577B1

  公开（公告）日：2018-12-12
• BI-FUNCTINAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Gouliaev Alex Haahr

  公开号：US20130281324A1

  公开（公告）日：2013-10-24

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.
• Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes
  作者：Jan Becher、Per Lauge Joergensen、Krystian Pluta、Niels J. Krake、Birgitte Falt-Hansen

  DOI：10.1021/jo00033a039

  日期：1992.3

  5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3. Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields. Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields. In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.