3-chloro-1-methyl-1H-pyrazole-4-carbaldehyde | 797798-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-1-methyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 1H-Pyrazole-4-carboxaldehyde, 3-chloro-1-methyl-；3-chloro-1-methylpyrazole-4-carbaldehyde
• CAS: 797798-26-6
• 化学式: C₅H₅ClN₂O
• mdl: MFCD22572495
• 分子量: 144.56
• InChiKey: OLVAYPUPZXSZFO-UHFFFAOYSA-N

物化性质

• 沸点：
  241.5±20.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-chloro-1-methyl-1H-pyrazole-4-carbaldehyde 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AS DIHYDROOROTATE DEHYDROGENASE INHIBITORS
  [FR] COMPOSÉS HÉTÉROCYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE LA DIHYDROOROTATE DÉSHYDROGÉNASE

  摘要：

  本文披露了一种通过调节DHODH来治疗受影响的疾病、紊乱或医疗状况的化合物、组合物和方法。这些化合物的实施例由以下的化学式(I)和化学式(II)表示：其中R1、R2、R3、R4、R5、R6、R7、R8、X1、X2、X3、X4、Y和Z在此定义。

  公开号：

  WO2021156787A1
• 作为产物：
  描述：

  1-甲基-1H-吡唑-4-甲醛 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到3-chloro-1-methyl-1H-pyrazole-4-carbaldehyde
  参考文献：
  名称：

  通过烯丙基硼化/环封闭-置换序列非对映选择性合成反式-2,3-二芳基（杂芳基）-3,6-二氢吡喃

  摘要：

  使用从相应的烯丙醇原位形成的烯丙基硼烷，通过烯丙基硼化/闭环复分解序列合成反式-2,3-二芳基（杂芳基）-二氢吡喃。因此，芳基（杂芳基）取代基以反式非对映选择性地安装在二氢吡喃环上。将这些二取代的二氢吡喃进一步转化成单糖状的四氢吡喃。

  DOI：

  10.1002/ejoc.201700448

文献信息

• Novel Diamino Derivatives of [1,2,4]Triazolo[1,5-a][1,3,5]triazine as Potent and Selective Adenosine A_2a Receptor Antagonists
  作者：Chi B. Vu、Deborah Pan、Bo Peng、Gnanasambandam Kumaravel、Glenn Smits、Xiaowei Jin、Deepali Phadke、Thomas Engber、Carol Huang、Jennifer Reilly、Stacy Tam、Donna Grant、Gregg Hetu、Russell C. Petter

  DOI：10.1021/jm0498396

  日期：2005.3.1

  Piperazine derivatives of 2-furanyl[1,2,4]triazolo[1,5-a][1,3,5]triazine have recently been demonstrated to be potent and selective adenosine A(2a) receptor antagonists with oral activity in rodent models of Parkinson's disease. We have replaced the piperazinyl group with a variety of linear, monocyclic, and bicyclic diamines. Of these diamines, (R)-2-(aminomethyl)pyrrolidine is a particularly potent and selective replacement for the piperazinyl group. With this diamine component, we have been able to prepare numerous analogues with low nanomolar affinity toward the A(2a) receptor and good selectivity with respect to the A(1) receptor (> 200-fold in some cases). Selected analogues from this series of [1,2,4]triazolo[1,5-a][1,3,5]triazine have now been shown to be orally active in the mouse catalepsy model.
• Iron-Catalyzed Synthesis of C2 Aryl- and <i>N</i>-Heteroaryl-Substituted Tetrahydropyrans
  作者：Cyril Bosset、Patrick Angibaud、Ian Stanfield、Lieven Meerpoel、Didier Berthelot、Amandine Guérinot、Janine Cossy

  DOI：10.1021/acs.joc.5b02371

  日期：2015.12.18

  An iron-catalyzed cyclization of hydroxy allylic derivatives into tetrahydropyrans possessing an N-heteroaryl at C2 is disclosed. The reaction proceeds with good yield and in high diastereoselectivity in favor of the more stable isomer. The diastereoselectivity results from an iron-induced reopening of the tetrahydropyrans, allowing a thermodynamic equilibration. The method allows access to a variety of 2,6-disubstituted as well as 2,4,6-trisubstituted tetrahydropyrans that could be considered as attractive scaffolds for the pharmaceutical industry.
• Lewis Basicity Modulation of <i>N</i>-Heterocycles: A Key for Successful Cross-Metathesis
  作者：Kevin Lafaye、Lionel Nicolas、Amandine Guérinot、Sébastien Reymond、Janine Cossy

  DOI：10.1021/ol502016h

  日期：2014.10.3

  Cross-metathesis involving N-heteroaromatic olefinic dervatives is disclosed. The introduction of an appropriate substitutent on the heteroaromatic ring decreases the lewis basicity of the nitrogen atom, thus preventing the deactivation of the ruthenium-centered catalyst. The reaction is quite general in terms of both N-heterocycles and olefinic partners.
• Piperazine Derivatives of [1,2,4]Triazolo[1,5-<i>a</i>][1,3,5]triazine as Potent and Selective Adenosine A₂_a Receptor Antagonists
  作者：Chi B. Vu、Bo Peng、Gnanasambandam Kumaravel、Glenn Smits、Xiaowei Jin、Deepali Phadke、Thomas Engber、Carol Huang、Jennifer Reilly、Stacy Tam、Donna Grant、Gregg Hetu、Liqing Chen、Jianbo Zhang、Russell C. Petter

  DOI：10.1021/jm0498405

  日期：2004.8.1

  The [1,2,4]triazolo[1,5-a]triazine derivative 3, more commonly known in the field of adenosine research as ZM-241385, has previously been demonstrated to be a potent and selective adenosine A(2a) receptor antagonist, although with limited oral bioavailability. This [1,2,4]triazolo[1,5-a]triazine core structure has now been improved by incorporating various piperazine derivatives. With some preliminary optimization, the A2a binding affinity of some of the best piperazine derivatives is almost as good as that of compound 3. The selectivity level over the adenosine A, receptor subtype for some of the more active analogues is also fairly high, >400-fold in some cases. Many compounds within this piperazine series of [1,2,4]triazolo[1,5-a]triazine have now been shown to have good oral bioavailability in the rat, with some as high as 89% (compound 35). More significantly, some piperazines derivatives of [1,2,4]triazolo[1,5-a]triazine also possessed good oral efficacy in rodent models of Parkinson's disease. For instance, compound 34 was orally active in the rat catalepsy model at 3 mg/kg. In the 6-hydroxydopamine-lesioned rat model, this compound was also quite effective, with a minimum effective dose of 3 mg/kg po.
• HETEROCYCLIC COMPOUNDS AS DIHYDROOROTATE DEHYDROGENASE INHIBITORS
  申请人：Janssen Biotech, Inc.

  公开号：EP4100124A1

  公开（公告）日：2022-12-14