N,N-二甲基环丙烷磺酰胺 | 146475-54-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 中文名称: N,N-二甲基环丙烷磺酰胺
• 英文名称: N,N-dimethylcyclopropanesulfonamide
• CAS: 146475-54-9
• 化学式: C₅H₁₁NO₂S
• 分子量: 149.214
• InChiKey: SWQZWHWDJOOMNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  N,N-二甲基环丙烷磺酰胺 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 2-[1-(Dimethylsulfamoyl)cyclopropyl]ethyl methanesulfonate
  参考文献：
  名称：

  稠合三环类化合物及其在药物中的应用

  摘要：

  本发明涉及一种稠合三环类化合物及其在药物中的应用，尤其是作为用于治疗和/或预防乙型肝炎的药物的应用。具体地说，本发明涉及通式(I)所示化合物或其立体异构体、互变异构体、氮氧化物、溶剂化物、代谢产物、药学上可接受的盐或它的前药，其中各变量如说明书所定义。本发明还涉及通式(I)所示化合物或其立体异构体、互变异构体、氮氧化物、溶剂化物、代谢产物、药学上可接受的盐或它的前药作为药物的用途，尤其是作为用于治疗和/或预防乙型肝炎的药物的用途。

  公开号：

  CN110903284A
• 作为产物：
  描述：

  3-氯-N,N-二甲基丙烷-1-磺酰胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以78%的产率得到N,N-二甲基环丙烷磺酰胺
  参考文献：
  名称：

  Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media

  摘要：

  Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J. Am. Chem. Soc. 1992,114,1743-1749), specifically, (a) below pH 7.2 by S(N)2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0. The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the alpha-deuterated N,N-dimethyl sulfonamide (12, R = Me). The evident sulfene formation processes in the reaction of triethylamine with ethanesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (<1.5), pointing to highly product-like transition states. Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).

  DOI：

  10.1021/jo00057a027

文献信息

• Charge-Transfer Complex Promoted Regiospecific C−N Bond Cleavage of Vicinal Tertiary Diamines
  作者：Ying Fu、Qin-Shan Xu、Chun-Zhao Shi、Zhengyin Du、Caiqin Xiao

  DOI：10.1002/adsc.201800591

  日期：2018.9.17

  A catalyst‐free, charge‐transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C−N

  提出了一种无催化剂，电荷转移的复合物，可促进磺酰氯与邻位叔二胺的偶联，从而生成磺酰胺。机理研究表明，这些反应是通过将邻位叔二胺电荷转移至磺酰氯而进行的，形成了不稳定的磺酰基季铵盐状复合物，从而诱导了邻位叔二胺的区域特异性分子内C-N键裂解。
• Preparation of sulfonamides from N-silylamines
  作者：Rajasekhar Reddy Naredla、Douglas A. Klumpp

  DOI：10.1016/j.tetlet.2013.08.034

  日期：2013.11

  Sulfonamides have been prepared in high yields by the reactions of N-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide. (C) 2013 Elsevier Ltd. All rights reserved.
• 稠合三环类化合物及其在药物中的应用
  申请人：广东东阳光药业有限公司

  公开号：CN110903284A

  公开（公告）日：2020-03-24

  本发明涉及一种稠合三环类化合物及其在药物中的应用，尤其是作为用于治疗和/或预防乙型肝炎的药物的应用。具体地说，本发明涉及通式(I)所示化合物或其立体异构体、互变异构体、氮氧化物、溶剂化物、代谢产物、药学上可接受的盐或它的前药，其中各变量如说明书所定义。本发明还涉及通式(I)所示化合物或其立体异构体、互变异构体、氮氧化物、溶剂化物、代谢产物、药学上可接受的盐或它的前药作为药物的用途，尤其是作为用于治疗和/或预防乙型肝炎的药物的用途。
• Organic sulfur mechanisms. 36. Cyclopropanesulfonyl chloride: its mechanisms of hydrolysis and reactions with tertiary amines in organic media
  作者：James F. King、Joe Y. L. Lam、Gabriele Ferrazzi

  DOI：10.1021/jo00057a027

  日期：1993.2

  Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J. Am. Chem. Soc. 1992,114,1743-1749), specifically, (a) below pH 7.2 by S(N)2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0. The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the alpha-deuterated N,N-dimethyl sulfonamide (12, R = Me). The evident sulfene formation processes in the reaction of triethylamine with ethanesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (<1.5), pointing to highly product-like transition states. Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).