2,5-dimethyl-1-(naphthyl)-pyrrole | 18494-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,5-dimethyl-1-(naphthyl)-pyrrole
• 英文别名: 2,5-dimethyl-1-(naphthalen-1-yl)-1H-pyrrole；1-(1-naphthalenyl)-2,5-dimethylpyrrole；2,5-dimethyl-1-(naphthalene-1-yl)-1H-pyrrole；2,5-dimethyl-1-naphthalen-1-ylpyrrole
• CAS: 18494-86-5
• 化学式: C₁₆H₁₅N
• mdl: MFCD01125292
• 分子量: 221.302
• InChiKey: UCWRRXOWTMTMQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2,5-dimethyl-1-(naphthyl)-pyrrole 在 哌啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 5-[(2,5-dimethyl-1-naphthalen-1-ylpyrrol-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：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2,5-dimethyl-1-(naphthyl)-pyrrole
  参考文献：
  名称：

  Knorr, Justus Liebigs Annalen der Chemie, 1886, vol. 236, p. 296,298

  摘要：

  DOI：

文献信息

• One-pot Tandem Reactions for Direct Conversion of Thiols and Disulfides to Sulfonic Esters, Alcohols to Bis(indolyl)methanes and Synthesis of Pyrroles Catalyzed by N-Chloro Reagents
  作者：Hojat Veisi、Meral Ataee、Leila Fatolahi、Shahram Lotfi

  DOI：10.2174/1570178611310020008

  日期：2013.4.1

  convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols

  已经描述了由硫醇和二硫化物方便地合成磺酸酯的方法。由硫醇原位制备磺酰氯的方法是用氯丁宁-T，氯化四丁基铵（t-Bu 4 NCl）和水氧化。然后使磺酰氯在同一反应容器中与苯酚衍生物反应。同样，在温和的条件下，使用TCCA / KBr / wet-SiO 2和N-取代的吡咯通过TCCA / KBr / wet-SiO 2从醇中轻松合成双（吲哚基）甲烷已在温和条件下以优异的收率完成。
• One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal–Knorr synthesis of pyrrole derivatives catalyzed by TCCA
  作者：Saba Hemmati、Mohammad Majid Mojtahedi、Mohammad Saeed Abaee、Zahra Vafajoo、Shokufe Ghahri Saremi、Mohammad Noroozi、Alireza Sedrpoushan、Meral Ataee

  DOI：10.1080/17415993.2012.744410

  日期：2013.8.1

  thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition

  描述了从硫醇和二硫化物方便地合成磺酸酯。从硫醇原位制备磺酰氯是通过用三氯异氰尿酸 (TCCA)、四丁基氯化铵 (t-Bu4NCl) 和水氧化来完成的。然后使磺酰氯在同一反应容器中进一步与苯酚衍生物反应。此外，使用 TCCA 作为催化剂，在温和的条件下，通过己烷-2,5-二酮与伯胺反应，以优异的产率轻松合成了 N-取代的吡咯。
• Synthesis of 2,5-Dimethyl-<i>N</i>-substituted Pyrroles Catalyzed by Diethylenetriaminepentaacetic Acid Supported on Fe₃O₄ Nanoparticles
  作者：Saba Hemmati、Pourya Mohammadi、Alireza Sedrpoushan、Behrooz Maleki

  DOI：10.1080/00304948.2018.1525668

  日期：2018.9.3

  addressing this issue, nanoparticles (NPs) have emerged as support materials due to their high surface areas and catalyst loading capacity, improved catalytic activity and dispersability in the reaction medium. Among the various nanoparticle supports, magnetic nanoparticles are efficient and readily available. They have high surface area resulting in high catalyst loading capacity and outstanding stability

  受当前对绿色化学和可持续化学要求的启发，有机反应中多相催化剂的开发已成为一个主要研究领域。这是由于这些材料相对于均质系统的潜在优势。这些优点包括简化回收、可重复使用、易于产品分离和整合到连续反应器和微反应器中。与多相催化剂相关的主要限制是它们的催化活性和选择性较低。在解决这个问题时，纳米颗粒 (NPs) 因其高表面积和催化剂负载能力、改进的催化活性和在反应介质中的分散性而成为载体材料。在各种纳米颗粒载体中，磁性纳米颗粒是高效且容易获得的。它们具有高表面积，从而导致高催化剂负载能力和出色的稳定性。更重要的是，磁性纳米粒子的磁分离比过滤或离心更有效，在用作核心磁性载体的各种磁性纳米粒子中，Fe3O4 纳米粒子可以说是研究最广泛的 13，因为它们具有良好的稳定性、易于合成和功能化，并且磁力分离容易，毒性低，价格便宜。已经使用贵金属、碳、二氧化硅和生物聚合物等材料对 Fe3O4 纳米粒子进行了改性
• Silica sulfuric acid (SSA) as a solid acid heterogeneous catalyst for one-pot synthesis of substituted pyrroles under solvent-free conditions at room temperature
  作者：Hojat Veisi

  DOI：10.1016/j.tetlet.2010.02.052

  日期：2010.4

  A variety of N-substituted pyrroles have been synthesized by reacting γ-diketones with amines, diamines or triamine in the presence of silica sulfuric acid (SSA) at room temperature under solvent-free conditions. The experiment protocol features simple operations, and the products are isolated in high to excellent yields (70–98%).

  通过在室温下在无溶剂硫酸二氧化硅（SSA）存在下，使γ-二酮与胺，二胺或三胺反应，可以合成出多种N-取代的吡咯。该实验方案操作简单，并且分离出的产品产率高至优异（70-98％）。
• An Efficient and Green Procedure for Synthesis of Pyrrole Derivatives by Paal-Knorr Condensation Using Sodium Dodecyl Sulfate in Aqueous Micellar
  作者：Hojat Veisi、Reza Azadbakht、Mehdi Ezadifar、Saba Hemmati

  DOI：10.1002/jhet.1069

  日期：2013.2

  A simple, economical, and green approach to the synthesis of N-substituted pyrroles using sodium dodecyl sulfate as surfactant in water is described. The experiment protocol features simple operations, and the products are isolated in high to excellent yields (60–98%).

  描述了一种使用十二烷基硫酸钠作为表面活性剂在水中合成N-取代的吡咯的简单，经济和绿色的方法。该实验方案操作简单，并且分离出的产品产率高至优异（60–98％）。