1,1-difluoro-2-morpholin-4-yl-2-oxo-ethanesulfonyl fluoride | 670-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 1,1-difluoro-2-morpholin-4-yl-2-oxo-ethanesulfonyl fluoride
• 英文别名: 1,1-difluoro-2-morpholino-2-oxo-ethanesulfonyl fluoride；1,1-Difluor-2-morpholino-2-oxo-aethansulfonylfluorid；(Difluor-fluorsulfonyl-essigsaeure)-morpholid；1,1-Difluoro-2-morpholin-4-yl-2-oxoethanesulfonyl fluoride
• CAS: 670-26-8
• 化学式: C₆H₈F₃NO₄S
• 分子量: 247.195
• InChiKey: RDYJBCANVHOIIC-UHFFFAOYSA-N

物化性质

• 沸点：
  346.3±42.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)
• 熔点：
  72-73 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1-difluoro-2-morpholin-4-yl-2-oxo-ethanesulfonyl fluoride 在 水 、 碳酸氢钠 、 sodium sulfite 、 碘 、 potassium iodide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 2,2-difluoro-2-iodo-1-morpholinoethanone
  参考文献：
  名称：

  Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions

  摘要：

  Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.

  DOI：

  10.1021/jo1005262
• 作为产物：
  描述：

  吗啉 、 四氟乙烷-beta-磺内酯 以 乙醚 为溶剂， 以45%的产率得到1,1-difluoro-2-morpholin-4-yl-2-oxo-ethanesulfonyl fluoride
  参考文献：
  名称：

  Reactions of Fluoroölefins with Sulfur Trioxide

  摘要：

  DOI：

  10.1021/ja01508a051

文献信息

• Introducing difluoromethylene sulfonamide group via nucleophilic addition of difluoromethylene anion with aromatic aldehydes
  作者：Jun-Li Li、Jin-Tao Liu

  DOI：10.1016/j.tet.2006.11.036

  日期：2007.1

  for the introduction of difluoromethylene sulfonamide or difluoromethylene group. Under different conditions, 2 reacted readily with aromatic aldehydes to give the corresponding difluoromethylene-containing alcohols or diols in moderate to good yields in the presence of potassium tert-butoxide. Difluoromethylene sulfonamide group was introduced into organic compounds directly for the first time by this

  为了引入二氟亚甲基磺酰胺或二氟亚甲基，开发了新的含氟合成子R 1 COCF 2 SO 2 R 2（2，R 1，R 2＝吗啉代，哌啶子基等）。在叔丁醇钾的存在下，在不同条件下，2容易与芳族醛反应，以中等至良好的收率得到相应的含二氟亚甲基的醇或二醇。通过这种方法首次将二氟亚甲基磺酰胺基团直接引入有机化合物中。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.2, 1.3.2, page 99 - 119
  作者：

  DOI：——

  日期：——
• Alpha-sulfopolyfluoromonocarboxylic acids and derivatives hydrolyzable thereto
  申请人：DU PONT

  公开号：US02852554A1

  公开（公告）日：1958-09-16
• Reactions of Fluoroölefins with Sulfur Trioxide
  作者：D. C. England、M. A. Dietrich、R. V. Lindsey

  DOI：10.1021/ja01508a051

  日期：1960.12
• Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions
  作者：Jieming Zhu、Wei Zhang、Laijun Zhang、Jun Liu、Ji Zheng、Jinbo Hu

  DOI：10.1021/jo1005262

  日期：2010.8.20

  Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.