N-[(trifluoromethyl)sulfonyl]-3-azatricyclo[3.2.1.0^2,4]octane | 957188-78-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-[(trifluoromethyl)sulfonyl]-3-azatricyclo[3.2.1.0^2,4]octane
• 英文别名: N-[(trifluoromethyl)sulfonyl]-3-azatricyclo[3.2.1.0(2,4)]octane；3-(trifluoromethylsulfonyl)-3-azatricyclo[3.2.1.02,4]octane
• CAS: 957188-78-2
• 化学式: C₈H₁₀F₃NO₂S
• 分子量: 241.234
• InChiKey: IJSQYNFUCRYHMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  37.15
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  降冰片烯 、 [N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ³-bromane 以 乙腈 为溶剂， 反应 5.0h， 以72%的产率得到N-[(trifluoromethyl)sulfonyl]-3-azatricyclo[3.2.1.0^2,4]octane
  参考文献：
  名称：

  A New Type of Imido Group Donor:  Synthesis and Characterization of Sulfonylimino-λ³-bromane that Acts as a Nitrenoid in the Aziridination of Olefins at Room Temperature under Metal-Free Conditions

  摘要：

  A stable sulfonylimino-lambda(3)-bromane, CF3SO2N--Br+C6H4-p -CF3, has been syntesized and structurally characterized for the first time. X-ray crystallographic analyses indicated a centrosymmetric dimer structure with little double-bond character for the "ylidic" Br-N bond. THe iminobromane serves as an efficient imido group donor and directly u ndergoes aziridination of olefins stereospecifically of alkenes under transition-metal-free conditions. The observed rate constants for aziridination of cis -cyclooctene are proportional to concentration of the olefin. The results suggest the involvement of a bimolicular transition state, in which an olefin attacks the sigma(*) N-Br orbital of iminobromane in the nitrenoid transfer process.

  DOI：

  10.1021/ja075811i

文献信息

• Synthesis and Structure of Hypervalent Diacetoxybromobenzene and Aziridination of Olefins with Imino-λ³-bromane Generated in Situ under Metal-Free Conditions
  作者：Md. Mahbubul Hoque、Kazunori Miyamoto、Norihiro Tada、Motoo Shiro、Masahito Ochiai

  DOI：10.1021/ol201868n

  日期：2011.10.21

  Ligand exchange of p-CF3C6H4BrF2 with acetoxy groups using AcOH and Ac2O affords (diacetoxybromo)benzene in a high yield, which undergoes azirldination of alkenes In the presence of TfNH2 and sulfamate esters in one pot under mild conditions. The azirldination with TfNH2 proceeds stereospecifically with retention of stereochemistry of olefins at room temperature using limiting amounts of olefins under transition-metal-free conditions. The one-pot aziridination procedure using sulfamate esters can be applied to the Intramolecular versions.