2,5-dichloro-1-methyl-1H-pyrrole | 56454-28-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2,5-dichloro-1-methyl-1H-pyrrole
• 英文别名: 2,5-Dichloro-1-methylpyrrole
• CAS: 56454-28-5
• 化学式: C₅H₅Cl₂N
• 分子量: 150.007
• InChiKey: IMBLERQXAUSQQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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-dichloro-1-methyl-1H-pyrrole 在 三乙烯二胺 、 二氯化二硫 、 sodium cyanide 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 53.0h， 生成 1,3,6,8-tetrachloro-2,7-dimethyl[1,2,5,6]tetrathiocino[3,4-c:7,8-c']dipyrrole
  参考文献：
  名称：

  Novel fused tetrathiocines as antivirals that target the nucleocapsid zinc finger containing protein of the feline immunodeficiency virus (FIV) as a model of HIV infection

  摘要：

  A novel series of fused tetrathiocines were prepared for evaluation of activity against the nucleocapsid protein of the feline immunodeficiency virus (FIV) in an in vitro cell culture approach. The results demonstrated that the compounds display potent nanomolar activity and low toxicity against this key model of HIV infection. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.047
• 作为产物：
  描述：

  N-甲基吡咯 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2,5-dichloro-1-methyl-1H-pyrrole
  参考文献：
  名称：

  NHC-有机催化的CAr-O键断裂：轻度接触2-羟基二苯甲酮

  摘要：

  N杂环卡宾（NHC）催化产生的酰基阴离子当量的Truce-Smiles重排已实现。所开发的方法包括裂解C Ar -O，C Ar -S或C Ar -N键以形成C Ar -C键，并能够获得2-羟基二苯甲酮，这是几种生物活性天然存在的重要结构基序产品。通过使用该程序，生物碱紫杉胺分三步合成。DFT计算和控制实验支持经典S NAr机理是与催化剂结合的Meisenheimer型中间体。该方法具有温和的反应条件，出色的官能团耐受性和广泛的底物范围，包括各种类别的（杂）芳烃。

  DOI：

  10.1002/anie.201610203

文献信息

• Site-Selective Thiolation of (Multi)halogenated Heteroarenes
  作者：Frederik Sandfort、Tobias Knecht、Tobias Pinkert、Constantin G. Daniliuc、Frank Glorius

  DOI：10.1021/jacs.0c01630

  日期：2020.4.15

  complementing established methodologies such as nucleophilic aromatic substitution or palladium-catalyzed coupling reactions. Experimental and computational studies suggest a radical chain mechanism with the key step being a homolytic aromatic substitution of the heteroaryl halide by an electrophilic thiyl radical, highlighting an underdeveloped reactivity mode of these radicals.

  报告了各种药物相关的富电子杂芳烃与硫醇的位点选择性硫醇化的一般和简单策略。这种温和而可靠的光催化协议能够在（多）卤化底物的最富电子位置进行 CS 耦合，补充已建立的方法，如亲核芳香取代或钯催化的耦合反应。实验和计算研究表明了一种自由基链机制，其关键步骤是杂芳基卤化物被亲电硫基自由基的均裂芳族取代，突出了这些自由基的不发达反应模式。
• A one-step synthesis of fused pentathiepinsElectronic supplementary information (ESI) available: characterization of compounds 2–5, 9, and 11. See http://www.rsc.org/suppdata/cc/b2/b203349f/
  作者：Lidia S. Konstantinova、Oleg A. Rakitin、Charles W. Rees

  DOI：10.1039/b203349f

  日期：2002.5.17

  Treatment of nucleophilic heterocycles like pyrroles and thiophene, and their tetrahydro derivatives, with S2Cl2 and a base in chloroform at room temperature provides a simple one-pot synthesis of heterocyclic fused mono and bis pentathiepins such as 2, 3, 4, 5, 9, and 11.

  在室温下用S2Cl2和氯仿中的碱处理诸如吡咯和噻吩之类的亲核杂环及其四氢衍生物，可以简单地一锅合成杂环稠合的单和双五硫平，例如2,3、4、5、9，和11。
• Direct synthesis of fused 1,2,3,4,5-pentathiepins
  作者：Stanislav A. Amelichev、Lidia S. Konstantinova、Konstantin A. Lyssenko、Oleg A. Rakitin、Charles W. Rees

  DOI：10.1039/b508186f

  日期：——

  Treatment of nucleophilic heterocycles like pyrroles and thiophenes, and their tetrahydro derivatives, with S2Cl2 and DABCO in chloroform at room temperature provides a simple one-pot synthesis of fused mono and bispentathiepins. N-Methylpyrrole and its 2-chloro and 2,5-dichloro derivatives and N-methylpyrrolidine all give the same dichloropentathiepin 1a. N-Ethyl, isopropyl and tert-butylpyrrolidine behave similarly; the isopropylpyrrolidine also gives the bispentathiepin 6 which undergoes an intriguing rearrangement to the symmetrical monopentathiepin 1c. N-Methyl and ethyl indole give either 2,3-dichloro derivatives 8 or the pentathiepinoindoles 9, depending upon the reaction conditions. Thiophene and tetrahydrothiophene give the pentathiepin 10. X-Ray crystal structures are provided for the pentathiepins 1a and 1d, and possible reaction pathways are suggested for the extensive cascade reactions reported.

  在室温下，将亲核性杂环如吡咯和噻吩及其四氢衍生物与S2Cl2和DABCO在氯仿中反应，可以简单地一步合成融合的单和双五元硫杂环戊烷。N-甲基吡咯及其2-氯和2,5-二氯衍生物以及N-甲基吡咯烷均生成相同的二氯五元硫杂环戊烷1a。N-乙基、异丙基和叔丁基吡咯烷的行为类似；异丙基吡咯烷还生成了双五元硫杂环戊烷6，后者经历了一个有趣的重组变为对称的单五元硫杂环戊烷1c。N-甲基和乙基吲哚根据反应条件分别生成2,3-二氯衍生物8或五元硫杂环戊烷吲哚9。噻吩和四氢噻吩生成五元硫杂环戊烷10。提供了五元硫杂环戊烷1a和1d的X射线晶体结构，并为报道的大量级联反应提出了可能的反应途径。
• First example of electrophilic substitution by addition–elimination (σ-substitution) in pyrroles
  作者：Michael De Rosa、Ines Brillembourg

  DOI：10.1039/c39860001585

  日期：——

  Reaction of 1-methylpyrrole with N-chloroacetanilide leads to the incorporation of an acetanilide moiety in the pyrrole ring by addition–elimination.

  1-甲基吡咯与N-氯代乙酰苯胺的反应通过加成-消除反应在吡咯环中引入了乙酰苯胺部分。
• BIPYRIDINE COMPOUND, TRANSITION METAL COMPLEX, AND METHOD FOR PRODUCTION OF CONJUGATED AROMATIC COMPOUND USING THE TRANSITION METAL COMPLEX
  申请人：Asaumi Taku

  公开号：US20100184978A1

  公开（公告）日：2010-07-22

  A bipyridine compound represented by the formula (1): wherein R 1 , R 2 and R 3 each independently represent a C1-C10 alkyl group which may be substituted etc., and R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom etc., a transition metal complex obtained by contacting a bipyridine compound represented by the formula (1) with a compound of a transition metal belonging to Group 9, 10 or 11, and a method for production of a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of the transition metal complex.

  一种以式(1)表示的联吡啶化合物：其中R1、R2和R3各自独立地表示可以被取代的C1-C10烷基等，而R4、R5、R6、R7和R8各自独立地表示氢原子等，通过将式(1)表示的联吡啶化合物与属于9、10或11族过渡金属的化合物接触而获得的过渡金属配合物，以及一种制备共轭芳香化合物的方法，包括在过渡金属配合物的存在下，将一个或两个离去基团与芳环结合的芳香化合物（A）与具有与上述芳香化合物（A）相同结构的芳香化合物（A）或结构不同于上述芳香化合物（A）且具有一个或两个离去基团与芳环结合的芳香化合物（B）反应。