(E)-N-tert-butyl-3-phenylprop-2-en-1-imine oxide | 914488-83-8

• 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: (E)-N-tert-butyl-3-phenylprop-2-en-1-imine oxide
• CAS: 914488-83-8
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: WRSFGWRUPJWTON-BXOUXZMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-tert-butyl-3-phenylprop-2-en-1-imine oxide 、 1-苯基-庚-2-炔-1-酮 以 甲苯 为溶剂， 以64%的产率得到(5-butyl-2-tert-butyl-3-styryl-2,3-dihydro-isoxazol-4-yl)-phenyl-methanone
  参考文献：
  名称：

  A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization

  摘要：

  A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described, The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives all isolable isoxazoline intermediate, which upon oxidation undergoes stereoselectivc extrusion of nitrosomethane to give aryl vinyl or divinyl ketones. (C) 2008 Elsevier Ltd. All right, reserved.

  DOI：

  10.1016/j.tet.2008.10.003
• 作为产物：
  描述：

  反式肉桂醛 、 N-叔丁基羟胺盐酸盐 在 碳酸氢钠 、 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到(E)-N-tert-butyl-3-phenylprop-2-en-1-imine oxide
  参考文献：
  名称：

  A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization

  摘要：

  A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described, The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives all isolable isoxazoline intermediate, which upon oxidation undergoes stereoselectivc extrusion of nitrosomethane to give aryl vinyl or divinyl ketones. (C) 2008 Elsevier Ltd. All right, reserved.

  DOI：

  10.1016/j.tet.2008.10.003

文献信息

• Enantioselective Synthesis of 4-Isoxazolines by 1,3-Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines
  作者：José Alemán、Alberto Fraile、Leyre Marzo、José Luis García Ruano、Cristina Izquierdo、Sergio Díaz-Tendero

  DOI：10.1002/adsc.201200033

  日期：2012.6.18

  The first organocatalytic enantioselective 1,3‐dipolar reaction between nitrones and alkynals catalyzed by (S)‐2‐(fluorodiphenylmethyl)pyrrolidine to give 4‐isoxazolines (2,3‐dihydroisoxazoles) with high enantiomeric excess, excellent yields and low catalyst loading (1–5 mol%) is presented. The catalytic loading could be reduced to 1 mol% with only slight increases in reaction times.

  （S）-2-（氟二苯基甲基）吡咯烷催化的硝酮与炔烃之间的第一个有机催化对映选择性1,3-偶极反应，得到对映体过量高，产率高，催化剂负载低的4-异恶唑啉（2,3-二氢异恶唑）（ 1-5％（摩尔）。催化负荷可以降低到1摩尔％，而反应时间仅稍微增加。
• A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization
  作者：Daniel P. Canterbury、Ildiko R. Herrick、Joann Um、K.N. Houk、Alison J. Frontier

  DOI：10.1016/j.tet.2008.10.003

  日期：2009.4

  A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described, The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives all isolable isoxazoline intermediate, which upon oxidation undergoes stereoselectivc extrusion of nitrosomethane to give aryl vinyl or divinyl ketones. (C) 2008 Elsevier Ltd. All right, reserved.