N,N-diethyl-3-chloropropanesulfonamide | 146475-50-5

• 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
• 英文名称: N,N-diethyl-3-chloropropanesulfonamide
• 英文别名: 3-chloro-N,N-diethylpropane-1-sulfonamide
• CAS: 146475-50-5
• 化学式: C₇H₁₆ClNO₂S
• 分子量: 213.729
• InChiKey: HQULYWCCNPCSNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• 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-diethyl-3-chloropropanesulfonamide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以75%的产率得到N,N-二乙基环丙烷磺酰胺
  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
• 作为产物：
  描述：

  3-氯丙烷磺酰氯 、 二乙胺 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 N,N-diethyl-3-chloropropanesulfonamide
  参考文献：
  名称：

  Synthetic Studies on Condensed-Azole Derivatives. II. Application of a Computer-Assisted Automated Synthesis Apparatus for the Synthesis of N-Substituted Sulfamoylpropylthioimidazo(1,2-b)pyridazines.

  摘要：

  为了提高3-(imidazo[1, 2-b]吡咯啉-6-基)硫丙烷磺酰胺（I）的抗哮喘活性，采用了在武田开发的计算机辅助自动合成设备对I的磺酰胺基团进行了改造。几种磺酰胺衍生物（1-24）很容易获得，确认了该自动合成设备在实验室中的实用性。这些衍生物的抗哮喘活性在血小板激活因子（PAF）诱导的支气管收缩中进行了测试。其中，哌啶-哌啶衍生物（13）显示出与I相当的活性。

  DOI：

  10.1248/cpb.43.1511

文献信息

• SULFONE SUBSTITUTED 2,3-DIHYDROIMIDAZO [1,2-C] QUINAZOLINE DERIVATIVES USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS AND DISEASES WITH ANGIOGENESIS
  申请人：Hentemann Martin

  公开号：US20110190281A1

  公开（公告）日：2011-08-04

  This invention relates to novel sulfone 2I3-dihydroimidazo[1,2-c]quinazoline compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for phosphotidylinositol-3-kinase (PI3K) inhibition and treating diseases associated with phosphotidylinositol-3-kinase (PI3K) activity, in particular treating hyper-proliferative and/or angiogenesis mediated disorders, as a sole agent or in combination with other active ingredients.

  本发明涉及新型磺酮2I3-二氢咪唑[1,2-c]喹唑啉化合物，含有这些化合物的制药组合物以及使用这些化合物或组合物来抑制磷脂酰肌醇-3-激酶（PI3K）并治疗与磷脂酰肌醇-3-激酶（PI3K）活性相关的疾病，特别是治疗增殖过度和/或介导血管生成的疾病，作为单一药物或与其他活性成分联合使用。
• Sulfone substituted 2,3-dihydroimidazo [1,2-C] quinazoline derivatives useful for treating hyper-proliferative disorders and diseases with angiogenesis
  申请人：Hentemann Martin F.

  公开号：US08859572B2

  公开（公告）日：2014-10-14

  This invention relates to novel sulfone 2I3-dihydroimidazo[1 l2-c]quinazoline compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for phosphotidylinositol-3-kinase (PI3K) inhibition and treating diseases associated with phosphotidylinositol-3-kinase (PI3K) activity, in particular treating hyper-proliferative and/or angiogenesis mediated disorders, as a sole agent or in combination with other active ingredients.

  本发明涉及新型磺酮2I3-二氢咪唑[1 l2-c]喹唑啉化合物、含有该类化合物的药物组合物以及利用该类化合物或组合物抑制磷脂酰肌醇-3-激酶（PI3K）并治疗与磷脂酰肌醇-3-激酶（PI3K）活性相关的疾病，特别是作为单一药物或与其他活性成分联合使用治疗过度增殖和/或介导血管生成的疾病。
• SULFONE SUBSTITUTED 2,3-DIHYDROIMIDAZO Ý1,2-C¨QUINAZOLINE DERIVATIVES USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS AND DISEASES WITH ANGIOGENESIS
  申请人：Bayer Schering Pharma AG

  公开号：EP2244721A2

  公开（公告）日：2010-11-03
• US8859572B2
  申请人：——

  公开号：US8859572B2

  公开（公告）日：2014-10-14
• [EN] SULFONE SUBSTITUTED 2,3-DIHYDROIMIDAZO [1,2-C] QUINAZOLINE DERIVATIVES USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS AND DISEASES WITH ANGIOGENESIS<br/>[FR] DÉRIVÉS DE 2,3-DIHYDROIMIDAZO [1,2-C] QUINAZOLINE À SUBSTITUTION SULFONE UTILISÉS POUR TRAITER DES TROUBLES HYPERPROLIFÉRANTS ET DES MALADIES ASSOCIÉES À L'ANGIOGÉNÈSE
  申请人：BAYER HEALTHCARE LLC

  公开号：WO2009091550A2

  公开（公告）日：2009-07-23

  This invention relates to novel sulfone 2I3-dihydroimidazo[1 l2-c]quinazoline compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for phosphotidylinositol-3-kinase (PI3K) inhibition and treating diseases associated with phosphotidylinositol-3-kinase (PI3K) activity, in particular treating hyper-proliferative and/or angiogenesis mediated disorders, as a sole agent or in combination with other active ingredients.