(RS)-3-(N,N-dibenzyl-N-methylammonio)cyclohept-1-ene trifluoromethanesulfonate | 1182829-13-5

• 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: (RS)-3-(N,N-dibenzyl-N-methylammonio)cyclohept-1-ene trifluoromethanesulfonate
• 英文别名: Dibenzyl-cyclohept-2-en-1-yl-methylazanium;trifluoromethanesulfonate
• CAS: 1182829-13-5
• 化学式: CF₃O₃S*C₂₂H₂₈N
• 分子量: 455.541
• InChiKey: RAYXIJOUZSPVQR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (RS)-3-(N,N-dibenzyl-N-methylammonio)cyclohept-1-ene trifluoromethanesulfonate 在 三氯乙酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.58h， 生成 (1RS,2SR,3RS)-1,2-epoxy-3-(N,N-dibenzyl-N-methylammonio)cycloheptane trifluoromethanesulfonate 、 (1RS,2SR,3SR)-1,2-epoxy-3-(N,N-dibenzyl-N-methylammonio)cycloheptane
  参考文献：
  名称：

  Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines

  摘要：

  The ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl3CCO2H gives exclusively the corresponding syn-epoxide for the 5-membered ring (> 99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr). Oxidation of the homoallylic amines 3-(N-benzylamino)methylcyclohex-1-ene and 3-(N,N-dibenzylamino)methylcyclohex-1-ene gave, in both cases, the corresponding N-protected 1,2-anti-2,3-syn-3-aminomethylcyclohexane-1,2-diol with high levels of diastereoselectivity (>= 90:10 dr). The versatile synthetic intermediates resulting from these oxidation reactions are readily transformed into a range of amino diols.

  DOI：

  10.1021/jo9012783
• 作为产物：
  描述：

  (RS)-3-(N,N-dibenzylamino)cyclohept-1-ene 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 反应 2.0h， 以21%的产率得到(RS)-3-(N,N-dibenzyl-N-methylammonio)cyclohept-1-ene trifluoromethanesulfonate
  参考文献：
  名称：

  Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines

  摘要：

  The ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl3CCO2H gives exclusively the corresponding syn-epoxide for the 5-membered ring (> 99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr). Oxidation of the homoallylic amines 3-(N-benzylamino)methylcyclohex-1-ene and 3-(N,N-dibenzylamino)methylcyclohex-1-ene gave, in both cases, the corresponding N-protected 1,2-anti-2,3-syn-3-aminomethylcyclohexane-1,2-diol with high levels of diastereoselectivity (>= 90:10 dr). The versatile synthetic intermediates resulting from these oxidation reactions are readily transformed into a range of amino diols.

  DOI：

  10.1021/jo9012783

文献信息

• Ammonium-Directed Oxidation of Cyclic Allylic and Homoallylic Amines
  作者：Christopher W. Bond、Alexander J. Cresswell、Stephen G. Davies、Ai M. Fletcher、Wataru Kurosawa、James A. Lee、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、James E. Thomson

  DOI：10.1021/jo9012783

  日期：2009.9.4

  The ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl3CCO2H gives exclusively the corresponding syn-epoxide for the 5-membered ring (> 99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr). Oxidation of the homoallylic amines 3-(N-benzylamino)methylcyclohex-1-ene and 3-(N,N-dibenzylamino)methylcyclohex-1-ene gave, in both cases, the corresponding N-protected 1,2-anti-2,3-syn-3-aminomethylcyclohexane-1,2-diol with high levels of diastereoselectivity (>= 90:10 dr). The versatile synthetic intermediates resulting from these oxidation reactions are readily transformed into a range of amino diols.