2-Methoxycarbonyldifluoromethanesulfonyl azide | 82386-31-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 2-Methoxycarbonyldifluoromethanesulfonyl azide
• 英文别名: Carbomethoxydifluoromethane sulfonyl azide；Methyl 2-azidosulfonyl-2,2-difluoroacetate
• CAS: 82386-31-0
• 化学式: C₃H₃F₂N₃O₄S
• 分子量: 215.137
• InChiKey: UPGSGTSKPUYQBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  亚硝基叔丁烷 、 2-Methoxycarbonyldifluoromethanesulfonyl azide 以 二氯甲烷 为溶剂， 生成 Carbomethoxydifluoromethyl t-butyl nitroxide
  参考文献：
  名称：

  Study of the electron-transfer initiated reaction of N,N-dichloro-5-iodo-3-oxa-octafluoropentane sulfonyl amide and carbomethoxydifluoromethane sulfonyl azide with 2-methyl-2-nitrosopropane

  摘要：

  The reactions of N,N-dichloro-5-iodo-3-oxa-octafluoropentane sulfonyl amide (1) and carbomethoxydifluoromethane sulfonyl azide (2) with 2-methyl-2-nitrosopropane (3) have been studied by EPR spectroscopy. Our results suggest that these reactions are initiated by electron transfer (ET) between the perfluoroalkane sulfonyl compounds and the donor 3. The reaction of the dichloroamide 1 with 3 yields either one of two products, i.e., the unsymmetrical nitroxide 4 or the symmetrical nitroxide 5, depending on the nature of the solvent and the amount of 1 used. Possible mechanistic paths are discussed.

  DOI：

  10.1016/0022-1139(95)03240-e
• 作为产物：
  描述：

  氟磺酰基二氟乙酸甲酯 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以82%的产率得到2-Methoxycarbonyldifluoromethanesulfonyl azide
  参考文献：
  名称：

  氟代烷烃磺酰基叠氮化物的合成及其作为氟代烷烃磺酰基腈前体的反应

  摘要：

  标题化合物与环己烷，Me 2 C = CMe 2，甲基硫醚和三苯基膦进行热解或光解，通过全氟烷烃磺酰基腈中间体得到相应的插入或加成产物。

  DOI：

  10.1016/s0040-4039(00)79026-5

文献信息

• Synthesis of fluoroalkanesulfonyl azides and their reactions as fluoroalkanesulfonyl nitrene precursors
  作者：Zhu Shi-zheng

  DOI：10.1016/s0040-4039(00)79026-5

  日期：1992.10

  Thermolysis or photolysis of the title compounds with cyclohexane, Me2C = CMe2, methyl sulfide and triphenyl phosphine gave the corresponding insertion or addition products via the perfluoroalkanesulfonyl nitrene intermediate.

  标题化合物与环己烷，Me 2 C = CMe 2，甲基硫醚和三苯基膦进行热解或光解，通过全氟烷烃磺酰基腈中间体得到相应的插入或加成产物。
• Reactions of fluoroalkanesulfonyl azides with pyrrole and its derivatives
  作者：Wanting Xiong、Yong Xin、Jianwei Han、Shizheng Zhu

  DOI：10.1016/j.jfluchem.2010.05.005

  日期：2010.8

  The reactions of fluoroalkanesulfonyl azides with pyrrole and its derivatives were studied. The reaction proceeded smoothly under mild conditions to give the 3-(fluoroalkanesulfonamido) pyrroles in good yield. The electron donating groups on the pyrrole core accelerated the reaction, while the electron withdrawing groups decelerated it. All the products were fully characterized by spectrum methods

  研究了氟代烷基磺酰基叠氮化物与吡咯及其衍生物的反应。反应在温和的条件下顺利进行，以高收率得到3-（氟代烷烃磺酰胺基）吡咯。吡咯核上的给电子基团加速了反应，而吸电子基团使反应减速。所有产品均通过光谱方法进行了充分表征，其中一种产品通过X射线衍射分析得到了进一步证实。提出了这些反应的可能的反应机理。
• An Efficient Synthesis of N′-(Fluoroalkylsulfonyl) Amidines by a Copper(I)-Catalyzed One-Pot Three-Component Reaction
  作者：Shizheng Zhu、Wanting Xiong、Yong Xin、Jingwei Zhao

  DOI：10.1055/s-0030-1258450

  日期：2011.4

  Fluoroalkylsulfonyl azides were successfully employed as an efficient reacting partner in copper(I)-catalyzed three-component couplings with terminal alkynes and amines to afford the corresponding N′-(fluoroalkylsulfonyl) amidines in good yields. Possible reaction pathways are proposed. multicomponent reactions - fluoroalkylsulfonyl azides - 1-alkynes - amines - amidines

  氟代烷基磺酰基叠氮化物已成功地用作铜（I）催化的三组分偶联剂与末端炔烃和胺的有效反应伙伴，以高收率提供了相应的N '-（氟代烷基磺酰基）am。提出了可能的反应途径。 多组分反应-氟烷基磺酰基叠氮化物-1-炔烃-胺-idine
• Reactions of fluoroalkanesulfonyl azides with cyclic vinyl ethers
  作者：Shi-Zheng Zhu、Gui-Fang Jin、Jing-Wei Zhao

  DOI：10.1016/s0022-1139(02)00290-7

  日期：2003.3

  The addition reactions of fluoroalkanesulfonyl azides to dihydropyran or dihydrofuran were studied. These reactions do not give the corresponding N-fluoroalkanesulfonyl azilidines but N-fluoroalkanesulfonyl-tetrahydropyranon-2-imines or N-fluoroalkanesulfonyl-tetrahydro-furano-2-imines. The reaction mechanism is discussed.

  研究了氟代烷烃磺酰叠氮与二氢吡喃或二氢呋喃的加成反应。这些反应没有得到相应的N-氟代烷烃磺酰基氮杂环丁烷，而是N-氟代烷烃磺酰基-四氢吡喃-2-亚胺或N-氟代烷烃磺酰基-四氢呋喃-2-亚胺。讨论了反应机理。
• Volkov, N. D.; Nazaretyan, V. P.; Yagupol'skii, L. M., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 454 - 459
  作者：Volkov, N. D.、Nazaretyan, V. P.、Yagupol'skii, L. M.

  DOI：——

  日期：——