cis-2,3-diphenyl-N-[(trifluoromethyl)sulfonyl]aziridine | 957188-81-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-2,3-diphenyl-N-[(trifluoromethyl)sulfonyl]aziridine
• 英文别名: cis-2,3-diphenyl-N-triflylaziridine；(2R,3S)-2,3-diphenyl-1-(trifluoromethylsulfonyl)aziridine
• CAS: 957188-81-7
• 化学式: C₁₅H₁₂F₃NO₂S
• 分子量: 327.327
• InChiKey: HTOPQPKXJPHDAS-FSWDVZBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-2,3-diphenyl-N-[(trifluoromethyl)sulfonyl]aziridine 在 红铝 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以82%的产率得到cis-2,3-diphenylaziridine
  参考文献：
  名称：

  Synthesis and Structure of Hypervalent Diacetoxybromobenzene and Aziridination of Olefins with Imino-λ³-bromane Generated in Situ under Metal-Free Conditions

  摘要：

  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.

  DOI：

  10.1021/ol201868n
• 作为产物：
  描述：

  顺式-二苯乙烯 、 三氟甲磺酰胺 在 [p-(trifluoromethyl)phenyl](diacetoxy)-λ3-bromane 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以79%的产率得到cis-2,3-diphenyl-N-[(trifluoromethyl)sulfonyl]aziridine
  参考文献：
  名称：

  Synthesis and Structure of Hypervalent Diacetoxybromobenzene and Aziridination of Olefins with Imino-λ³-bromane Generated in Situ under Metal-Free Conditions

  摘要：

  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.

  DOI：

  10.1021/ol201868n

文献信息

• 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
  作者：Masahito Ochiai、Takao Kaneaki、Norihiro Tada、Kazunori Miyamoto、Hiroshi Chuman、Motoo Shiro、Satoko Hayashi、Waro Nakanishi

  DOI：10.1021/ja075811i

  日期：2007.10.1

  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.
• 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.