1-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole | 54609-18-6

• 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-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole
• 英文别名: 1-(4-ethoxyphenyl)-2,5-dimethylpyrrole
• CAS: 54609-18-6
• 化学式: C₁₄H₁₇NO
• mdl: MFCD03482748
• 分子量: 215.295
• InChiKey: ZDIOYIPJINVOQA-UHFFFAOYSA-N

物化性质

• 熔点：
  63 °C
• 沸点：
  331.3±30.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole 在 四氯化锡 、 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-Cyclopropyl-6-(4-ethoxy-phenyl)-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazine
  参考文献：
  名称：

  Synthesis and biological evaluation of 6-aryl-6 H -pyrrolo[3,4- d ]pyridazine derivatives: high-affinity ligands to the α 2 δ subunit of voltage gated calcium channels

  摘要：

  A novel class of 6-aryl-6H-pyrrolo[3,4-d]pyridazine ligands for the alpha(2)delta subunit of voltage-gated calcium channels has been described. Substitutions in the aryl ring of the molecule were generally not tolerated, and resulted in diminished binding to the alpha(2)delta subunit. Modifications to the pyridazine ring revealed numerous permissive substitutions, and detailed SAR studies were carried out in this portion of the molecule. Replacement of the pyridazine ring methyl group with an aminomethyl functionality provided greatly improved potency over the initial lead. The initial lead compound displayed good rat pharmacokinetic properties, and was shown to be efficacious in the Chung model for neuropathic pain in rats. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.036
• 作为产物：
  描述：

  2,5-己二酮 、 对乙氧基苯胺 在 氨基磺酸 作用下， 反应 1.0h， 以96%的产率得到1-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole
  参考文献：
  名称：

  氨基磺酸作为合成吡咯、呋喃和噻吩衍生物的高效且可重复使用的催化体系

  摘要：

  氨基磺酸首次被用作一种高效且可重复使用的催化体系，用于从 1,4-二酮合成杂芳烃，如吡咯、呋喃和噻吩衍生物。与报道的结果相比，这种新程序在更短的反应时间和更低的反应温度下显着提高了反应速率和产率。回收的催化剂可以在活性逐渐降低的情况下重新用于后续运行。最重要的特点是反应过程是均相的，而分离过程是多相的，这在其他催化剂中是很常见的，因此具有良好的技术应用特性。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:144–148, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20389

  DOI：

  10.1002/hc.20389

文献信息

• Sulfamic acid as efficient and reusable catalytic system for the synthesis of pyrrole, furan, and thiophene derivatives
  作者：Haitang Luo、Yuru Kang、Qi Li、Liming Yang

  DOI：10.1002/hc.20389

  日期：2008.3

  Sulfamic acid has been utilized for the first time as an efficient and reusable catalytic system for the synthesis of heteroaromatics such as pyrrole, furan, and thiophene derivatives from 1,4-diketones. This new procedure offers significant improvements in the reaction rates and yields in a shorter reaction time and a lower reaction temperature contrasted with the reported results. The recovered catalyst

  氨基磺酸首次被用作一种高效且可重复使用的催化体系，用于从 1,4-二酮合成杂芳烃，如吡咯、呋喃和噻吩衍生物。与报道的结果相比，这种新程序在更短的反应时间和更低的反应温度下显着提高了反应速率和产率。回收的催化剂可以在活性逐渐降低的情况下重新用于后续运行。最重要的特点是反应过程是均相的，而分离过程是多相的，这在其他催化剂中是很常见的，因此具有良好的技术应用特性。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:144–148, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20389
• An efficient synthesis of N-substituted pyrroles catalyzed by MgI2 etherate
  作者：Yongdong Zhang、Guodong Weng、Jingyan Chen、Danting Ma、Xingxian Zhang

  DOI：10.1515/mgmc-2014-0031

  日期：2014.1.1

  We describe a convenient and useful procedure for the synthesis of various 2,5-dimethyl-N-substituted pyrrole derivatives by the addition of 2,5-hexadione with aromatic amines, heteroaromatic amines and aliphatic amines catalyzed by MgI

  我们描述了一种方便实用的程序，通过将2,5-己二酮与芳香胺、杂环胺和脂肪胺在MgI催化下加成，合成各种2,5-二甲基-N-取代吡咯衍生物。

• Synthesis of Precursors of 4-Phosphino-1<i>H</i>-pyrrole-3-carbaldehyde Derivatives
  作者：Radomyr V. Smaliy、Aleksandra A. Chaykovskaya、Nataliya A. Shtil、Aleksandr S. Savateev、Aleksandr N. Kostyuk

  DOI：10.1002/hc.21069

  日期：2013.3

  In this work, possible approaches to the synthesis of 1,2,5-substituted 4-phosphoryl-3-formylpyrroles have been considered. As a result, two methods for the synthesis of 4-(diphenylphosphoryl)-1-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole-3-carbal-dehyde were proposed; the highest yields gives formylation of 3-(diphenylphosphorothioyl)-1-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole. The formyl fragment was

  在这项工作中，已经考虑了合成 1,2,5-取代 4-phosphoryl-3-formylpyrroles 的可能方法。因此，提出了两种合成4-(二苯基磷酰基)-1-(4-乙氧基苯基)-2,5-二甲基-1H-吡咯-3-碳醛的方法；最高产率得到 3-(二苯基硫代磷酰基)-1-(4-乙氧基苯基)-2,5-二甲基-1H-吡咯的甲酰化。用苯乙胺成功地将甲酰基片段转化为席夫碱，并用硅氯仿将磷酰基还原为膦，这为合成手性双齿膦配体提供了一种很有前景的方法。© 2013 Wiley Periodicals, Inc. 杂原子化学 24:146–151, 2013; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.21069
• Treatment of neuropathic pain with 6h-pyrrolo[3,4-d]pyridazine compounds
  申请人：Anker Burke Naomi

  公开号：US20060154929A1

  公开（公告）日：2006-07-13

  6H-pyrrolo[3,4-d]pyridazine compounds and methods of their use of as ligands of voltage gated calcium channels (VGCC), useful in the treatment of neuropathic pain, and psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, panic, and bipolar disorder, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other.

  6H-吡咯并[3,4-d]吡嗪化合物及其作为电压门控钙通道（VGCC）配体的使用方法，可用于治疗神经病性疼痛、精神和情绪障碍，例如精神分裂症、焦虑、抑郁、惊恐和双相情感障碍，以及治疗疼痛、帕金森病、认知功能障碍、癫痫、昼夜节律紊乱、药物成瘾、药物滥用、戒断症状等。
• Treatment of neuropathic pain with 6H-pyrrolo[3,4-d]pyridazine compounds
  申请人：Merck & Co. Inc.

  公开号：US07465730B2

  公开（公告）日：2008-12-16

  6H-pyrrolo[3,4-d]pyridazine compounds and methods of their use of as ligands of voltage gated calcium channels (VGCC), useful in the treatment of neuropathic pain, and psychiatric and mood disorders such as, for example, schizophrenia, anxiety, depression, panic, and bipolar disorder, as well as in the treatment of pain, Parkinson's disease, cognitive dysfunction, epilepsy, circadian rhythm disorders, drug addiction, drug abuse, drug withdrawal and other.

  6H-吡咯并[3,4-d]吡嗪化合物及其作为电压门控钙通道（VGCC）配体的应用方法，可用于治疗神经病理性疼痛和精神和情绪障碍，例如精神分裂症、焦虑、抑郁、恐慌和躁症，以及治疗疼痛、帕金森氏病、认知功能障碍、癫痫、昼夜节律紊乱、药物成瘾、药物滥用、药物戒断等。