N-benzyl-N-nitrosotrifluoromethanesulfonamide | 114532-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-N-nitrosotrifluoromethanesulfonamide
• 英文别名: N-benzyl-1,1,1-trifluoro-N-nitrosomethanesulfonamide
• CAS: 114532-98-8
• 化学式: C₈H₇F₃N₂O₃S
• 分子量: 268.216
• InChiKey: CBOFPDWRQHCTOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.0±50.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-nitrosotrifluoromethanesulfonamide 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 氘代氯仿 为溶剂， 生成 三氟甲磺酸苄酯
  参考文献：
  名称：

  Alkyl diazonium ion pairs and deamination. Part 45. The preparation of carbonium ions and other high-energy alkylating agents under mild conditions

  摘要：

  DOI：

  10.1021/ja00219a082
• 作为产物：
  描述：

  N-苯基三氟甲磺酸甲胺 在 sodium hydroxide 、 dinitrogen tetraoxide 、 sodium carbonate 作用下， 生成 N-benzyl-N-nitrosotrifluoromethanesulfonamide
  参考文献：
  名称：

  Alkyl diazonium ion pairs and deamination. Part 45. The preparation of carbonium ions and other high-energy alkylating agents under mild conditions

  摘要：

  DOI：

  10.1021/ja00219a082

文献信息

• Electronic and Steric Effects in Thermal Denitrosation of <i>N</i>-Nitrosoamides
  作者：Ron W. Darbeau、Edson V. Perez、Jennifer I. Sobieski、William A. Rose、Maria C. Yates、Benjamin J. Boese、Nyla R. Darbeau

  DOI：10.1021/jo001144z

  日期：2001.8.1

  N-Alkyl-N-nitrosoamides undergo competitive reactions whose rates are dependent upon the interplay of a number of factors. There already exists a significant body of work delineating the effects of pH on the partitioning of the nitrosoamides along their deaminative (-N-2) and denitrosative (-"NO+") pathways. In this paper, the issue of pH dependence is discussed with particular attention to nitrosoamide decompositions in nonaqueous media. The role of the acidity of the medium in the partitioning of the nitrosoamide between deamination and denitrosation and in the choice of deaminative pathways is revisited. In nonaqueous media under near-neutral conditions, the partitioning's pH dependence is evidently accompanied by a sensitivity to structural features in the nitrosoamide. Thus, diminution of steric crowding around the N-nitroso moiety as well as the presence of strongly electron-withdrawing acyl units (i.e., those derived from strong acids, e.g., tosyl and trifyl) increase the relative yield of amides by encouraging the denitrosative pathway. A mechanism for thermal denitrosation of nitrosoamides under near-neutral conditions is proposed in which rapid protonation at the acyl O rather than slow protonation at the amidic N is the first step in the reaction profile. A rate-limiting, bimolecular reaction between the C-conjugate acid and adventitious nucleophiles at the nitrosyl group then occurs followed by rapid tautomerization to amide.
• WHITE, EMIL H.;DEPINTO, JEFFREY T.;POLITO, ALBERT J.;BAUER, INES;ROSWELL,+, J. AMER. CHEM. SOC., 110,(1988) N 11, 3708-3709
  作者：WHITE, EMIL H.、DEPINTO, JEFFREY T.、POLITO, ALBERT J.、BAUER, INES、ROSWELL,+

  DOI：——

  日期：——