3-chloro-N,N-dimethylbenzenesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-N,N-dimethylbenzenesulfonamide
• 英文别名: 3-chloro-N,N-dimethylbenzene-1-sulfonamide
• 化学式: C₈H₁₀ClNO₂S
• mdl: MFCD18426341
• 分子量: 219.692
• InChiKey: XLQKZEOINNDMTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-N,N-dimethylbenzenesulfonamide 、 乙基氯化镁 在 N-甲基吡咯烷酮 、 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以93%的产率得到3-ethyl-N,N-dimethylbenzenesulfonamide
  参考文献：
  名称：

  铁催化氯苯磺酰胺与烷基格氏试剂的C（sp 2）–C（sp 3）交叉偶联：进入烷基化芳烃领域

  摘要：

  烷基化苯磺酰胺是有机合成中高度重要的化合物，包括药物，农用化学品和增塑剂的生产。我们报告了在温和且可持续的条件下，铁催化的氯苯磺酰胺与烷基格氏试剂的C（sp 2）–C（sp 3）交叉偶联。电子和空间变化的苯甲磺酰胺以及具有挑战性的含β-氢的烷基有机金属化合物均能以高收率或优异的收率提供烷基化的苯磺酰胺。磺酰胺代表了铁催化交叉偶联反应中最活泼的活化基团。该方法提供了准备用于药物化学应用和无痕还原裂解的烷基化苯磺酰胺。

  DOI：

  10.1021/acs.joc.8b02886
• 作为产物：
  描述：

  3-氯苯硫酚 、 N,N-二甲基甲酰胺 在 copper diacetate 、 肉桂酸 、 copper(l) chloride 作用下， 反应 24.0h， 以51%的产率得到3-chloro-N,N-dimethylbenzenesulfonamide
  参考文献：
  名称：

  Copper-mediated S–N formation via an oxygen-activated radical process: a new synthesis method for sulfonamides

  摘要：

  通过氧活化的自由基过程，已开发出一种铜介导的磺胺酰胺的直接合成。

  DOI：

  10.1039/c4cc01353k

文献信息

• METHOD FOR MANUFACTURING CONJUGATED AROMATIC COMPOUND
  申请人：Oda Seiji

  公开号：US20110275859A1

  公开（公告）日：2011-11-10

  A method for manufacturing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (A) does not have (c1) a group represented by the following formula (10): wherein A 1 represents a C1-C20 alkoxy group etc.; (g1) a C1-C20 alkyl group which may be substituted with a fluorine atom etc.; and (h1) a C2-C20 acyl group which may be substituted with a fluorine atom etc., at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) wherein the aromatic compound (B) is structurally different from the above-mentioned aromatic compound (A), one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (B) does not have the above-mentioned (c1), (g1) and (h1) at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, in the presence of (i) a nickel compound, (ii) a metal reducing agent, (iii) at least one ligand (L1) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-withdrawing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-withdrawing group and having no substituent at 2- and 9-positions, and (iv) at least one ligand (L2) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-releasing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-releasing group and having no substituent at 2- and 9-positions.

  一种制备共轭芳香化合物的方法，包括将含有一个或两个离去基团的芳香化合物（A）与含有相同结构的上述芳香化合物（A）或结构不同的芳香化合物（B）反应，其中这些离去基团选自碘原子、溴原子和氯原子，与芳香环结合，而芳香化合物（A）没有以下式（10）所代表的基团：其中A1代表C1-C20烷氧基等；（g1）代表C1-C20烷基基团，可能被氟原子等取代；以及（h1）代表C2-C20酰基基团，可能被氟原子等取代，与离去基团结合的碳原子的相邻碳原子处没有上述（c1）、（g1）和（h1），在（i）镍化合物、（ii）金属还原剂、（iii）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L1），具有至少一个吸电子基团且在3-、6-、3′-和6′-位置没有取代基，以及（iv）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L2），具有至少一个释电子基团且在3-、6-、3′-和6′-位置没有取代基团的情况下，在上述离去基团结合的碳原子的相邻碳原子处进行反应。
• METHOD FOR PRODUCING CONJUGATED AROMATIC COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2233459A1

  公开（公告）日：2010-09-29

  A method for producing 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 a nickel compound, a ligand, a manganese salt and a metal reducing agent.

  一种生产共轭芳香族化合物的方法，包括在镍化合物、配体、锰盐和金属还原剂的存在下，使一个或两个离去基团键合在芳香环上的芳香族化合物（A）与结构与上述芳香族化合物（A）相同的芳香族化合物（A）或结构与上述芳香族化合物（A）不同且一个或两个离去基团键合在芳香环上的芳香族化合物（B）反应。
• Simple N , N- dimethyl phenylsulfonamides show potent anticonvulsant effect in two standard epilepsy models
  作者：Tomoyuki Tanaka、Nana Yajima、Tomoko Kiyoshi、Yoshiki Miura、Seiji Iwama

  DOI：10.1016/j.bmcl.2016.11.035

  日期：2017.1

  Optimization of the previously reported benzothiazine analogue A led to the identification of compound 1, which showed anti-convulsant activity in two golden standard animal models of seizure, the MES and scPTZ models. Structure-activity relationship investigation of compound 1 revealed compounds 2, 6 and 19 as attractive anti-epileptic drug (AED) candidates with potent anticonvulsant effect in both the MES and scPTZ models. As these compounds are structurally different from existing AEDs, determination of their mechanism of actions could provide clues to understanding current therapy-resistant seizures. Moreover, these simple phenylsulfoneamide compounds could be good starting points for searching broad spectrum AEDs by such in vivo screening. (C) 2016 Elsevier Ltd. All rights reserved.
• HAY, JAMES V., PESTIC. SCI., 29,(1990) N, C. 247-261
  作者：HAY, JAMES V.

  DOI：——

  日期：——
• US8598349B2
  申请人：——

  公开号：US8598349B2

  公开（公告）日：2013-12-03