5-二甲氨基-1,3-二甲基-1H-吡唑-4-甲醛 | 26990-64-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5-二甲氨基-1,3-二甲基-1H-吡唑-4-甲醛
• 英文名称: 5-dimethylamino-1,3-dimethyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 5-(dimethylamino)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde；5-(dimethylamino)-1,3-dimethylpyrazole-4-carbaldehyde
• CAS: 26990-64-7
• 化学式: C₈H₁₃N₃O
• mdl: MFCD10690081
• 分子量: 167.211
• InChiKey: LUYRUQPYHUYINP-UHFFFAOYSA-N

物化性质

• 沸点：
  300.0±35.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-二甲氨基-1,3-二甲基-1H-吡唑-4-甲醛 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 6.0h， 生成 2-[5-(Dimethylamino)-1,3-dimethylpyrazol-4-yl]-1-(3-methoxypropyl)-5-oxopyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides

  摘要：

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.

  DOI：

  10.1021/co4001277
• 作为产物：
  描述：

  1,3-二甲基-5-吡唑酮 在 三氯氧磷 作用下， 生成 5-二甲氨基-1,3-二甲基-1H-吡唑-4-甲醛
  参考文献：
  名称：

  Identification of antitumor activity of pyrazole oxime ethers

  摘要：

  A series of pyrazole oxime ether derivatives were prepared and examined as cytotoxic agents. In particular, 5-phenoxypyrazole was comparable to doxorubicin, while exhibiting very potent cytotoxicity against XF 498 and HCT15. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.082

文献信息

• Introduction of <i>N</i>‐Containing Heterocycles into Pyrazole by Nucleophilic Aromatic Substitution
  作者：Min‐Sup Park、Hyun‐Ja Park、Koon Ha Park、Kee‐In Lee

  DOI：10.1081/scc-120030741

  日期：2004.12.31

  Abstract The nucleophilic aromatic substitution on 5‐chloropyrazoles activated by the electron‐withdrawing formyl group offers a useful method to introduce a wide range of N‐containing heterocycles into them. The rate of reaction was greatly affected by the electronic nature of the N‐1 substitution.

  摘要 吸电子甲酰基活化的 5-氯吡唑上的亲核芳香取代为将各种含氮杂环引入其中提供了一种有用的方法。N-1取代的电子性质对反应速率有很大影响。
• Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Dmitry S. Granat、Eugeniy N. Ostapchuk、Dmitriy V. Kryvoruchko、Oleksandr O. Grygorenko

  DOI：10.1021/co4001277

  日期：2014.3.10

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.
• Identification of antitumor activity of pyrazole oxime ethers
  作者：Hyun-Ja Park、Kyung Lee、Su-Jin Park、Bangle Ahn、Jong-Cheol Lee、HeeYeong Cho、Kee-In Lee

  DOI：10.1016/j.bmcl.2005.03.082

  日期：2005.7

  A series of pyrazole oxime ether derivatives were prepared and examined as cytotoxic agents. In particular, 5-phenoxypyrazole was comparable to doxorubicin, while exhibiting very potent cytotoxicity against XF 498 and HCT15. (c) 2005 Elsevier Ltd. All rights reserved.