1-(2,4-dimethylphenyl)-2,5-dimethyl-1H-pyrrole | 140137-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2,4-dimethylphenyl)-2,5-dimethyl-1H-pyrrole
• 英文别名: N-(2',4'-dimethylphenyl)-2,5-dimethylpyrrole；1-(2,4-dimethylphenyl)-2,5-dimethylpyrrole
• CAS: 140137-33-3
• 化学式: C₁₄H₁₇N
• mdl: MFCD03576673
• 分子量: 199.296
• InChiKey: QUOSFPJTOSHSQI-UHFFFAOYSA-N

物化性质

• 沸点：
  310.4±31.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethylphenyl)-2,5-dimethyl-1H-pyrrole 在 哌啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 5-[[1-(2,4-dimethylphenyl)-2,5-dimethylpyrrol-3-yl]methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype

  摘要：

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.049
• 作为产物：
  描述：

  2,5-己二酮 、 2,4-二甲基苯胺 在 草酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以92%的产率得到1-(2,4-dimethylphenyl)-2,5-dimethyl-1H-pyrrole
  参考文献：
  名称：

  用于通过 Paal-Knorr 反应有机催化合成吡咯的天然有机酸

  摘要：

  在这项研究中，常见的天然有机酸，即草酸、丙二酸、琥珀酸、酒石酸和柠檬酸（作为安全、廉价和可生物降解的有机催化剂）已被用于 Paal-Knorr 吡咯合成。证明有机催化反应在 60 °C 下在乙醇中是有效的。然而，反应速率主要取决于官能团在底物芳环上的性质和位置。这种无金属工艺可以容忍一系列官能团，应该被视为制药行业的一项资产，因为在吡咯支架的合成过程中不会发生金属污染。

  DOI：

  10.1007/s11164-020-04260-2

文献信息

• Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines
  作者：Xi Chen、Meng Yang、Min Zhou

  DOI：10.1016/j.tetlet.2016.10.029

  日期：2016.11

  An efficient and facile Pd(OCOCF3)2-catalyzed one-pot cascade protocol has been developed for the synthesis of multiple substituted pyrroles in good to excellent yields. Unlike the reported method starting from the 2-alkenal-1,3-carbonyl compounds, the process utilizes the less reactive 5-hexen-2-one and the method has great potential as a complement to the current developed methods.

  已经开发了一种有效且简便的Pd（OCOCF 3）2催化的一锅级联方案，用于合成多个取代的吡咯，产率高至优异。与报道的从2-链烯基-1,3-羰基化合物开始的方法不同，该方法利用了反应性较低的5-己烯-2-酮，该方法具有很大的潜力作为对当前开发方法的补充。
• Microwave assisted synthesis of pyrroles
  作者：Timothy N Danks

  DOI：10.1016/s0040-4039(99)00620-6

  日期：1999.5

  The synthesis of pyrroles by reaction of hexane-2,5-dione with primary amines has been shown to occur in less than 2 minutes under microwave activation.

  已经表明，在微波活化下，在不到2分钟的时间内，通过己烷-2，5-二酮与伯胺的反应合成吡咯。
• Hazlewood et al., Journal and Proceedings - Royal Society of New South Wales, 1937, vol. 71, p. 92,101
  作者：Hazlewood et al.

  DOI：——

  日期：——
• Synthesis of Pyrrole Derivatives Promoted by Fe(ClO4)3/SiO2 as an Environmentally Friendly Catalyst
  作者：K. Arabpourian、F. K. Behbahani

  DOI：10.1134/s1070428019050166

  日期：2019.5

  N-Substituted pyrroles have been prepared in high isolated yields (702-99%) by the reaction of hexane-2,5-dione with amines or diamines in the presence of Fe(ClO4)(3)/SiO2 at ambient temperature under solvent-free conditions. The experimental procedure involves simple operations, and the products are readily separated by short column chromatography. The same reaction of hexane-2,5-dione with amines containing electron-acceptor substituents, such as 4-nitroaniline, resulted in fair yields of pyrrole derivatives.
• Synthesis of Fe₃O₄@<i>L</i>-proline@SO₃H as a novel and reusable acidic magnetic nanocatalyst and its application for the synthesis of <i>N</i>-substituted pyrroles at room temperature under ultrasonic irradiation and without solvent
  作者：Fatemeh Shokri、Farahnaz K. Behbahani

  DOI：10.1080/24701556.2021.1963278

  日期：2022.8.3