ethanesulfonyl-1,1-d₂ chloride | 138236-00-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 英文名称: ethanesulfonyl-1,1-d₂ chloride
• 英文别名: ethanesulfonyl-1,1-d3 chloride；sulfonyl chloride 2,2-dideuteroethylsulfonylchlroide；1,1-Dideuterioethanesulfonyl chloride
• CAS: 138236-00-7
• 化学式: C₂H₅ClO₂S
• 分子量: 130.564
• InChiKey: FRYHCSODNHYDPU-CBTSVUPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethanesulfonyl-1,1-d₂ chloride 在 sodium hydroxide 作用下， 生成
  参考文献：
  名称：

  King; Lam; Skonieczny, Journal of the American Chemical Society, 1992, vol. 114, # 5, p. 1743 - 1749

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基磺酰氯 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙二醇二甲醚 、 重水 为溶剂， 生成 ethanesulfonyl-1,1-d₂ chloride
  参考文献：
  名称：

  [EN] DEUTERATED BARICITINIB
  [FR] BARICITINIB DEUTÉRIÉ

  摘要：

  在一个实施例中，本发明提供了一种化合物，其化学式为I：或其药用可接受的盐，其中化学式I中所示的变量如规范中所定义。

  公开号：

  WO2014028756A1

文献信息

• 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).
• King, J. F.; Lam, J. Y. L.; Skonieczny, S., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 59, # 1-4, p. 177 - 180
  作者：King, J. F.、Lam, J. Y. L.、Skonieczny, S.

  DOI：——

  日期：——