5-benzo[1,3]dioxol-5-yl-2-methyl-3-styryl-2,3-dihydro-isoxazole-4-carboxylic acid ethyl ester | 1152672-02-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 5-benzo[1,3]dioxol-5-yl-2-methyl-3-styryl-2,3-dihydro-isoxazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(1,3-benzodioxol-5-yl)-2-methyl-3-[(E)-2-phenylethenyl]-3H-1,2-oxazole-4-carboxylate
• CAS: 1152672-02-0
• 化学式: C₂₂H₂₁NO₅
• 分子量: 379.412
• InChiKey: VYEZDBHYFFQAKM-PKNBQFBNSA-N

物化性质

• 沸点：
  508.3±60.0 °C(predicted)
• 密度：
  1.318±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-benzo[1,3]dioxol-5-yl-2-methyl-3-styryl-2,3-dihydro-isoxazole-4-carboxylic acid ethyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(benzo[1,3]dioxole-5-carbonyl)-5-phenyl-penta-2,4-dienoic acid ethyl ester 、 2-(benzo[1,3]dioxole-5-carbonyl)-5-phenyl-penta-2,4-dienoic acid ethyl ester
  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：

  N-[(2E)-3-phenylprop-2-enylidene]methanamine N-oxide 、 ethyl 3-(benzo[d][1,3]dioxol-5-yl)propiolate 以 甲苯 为溶剂， 反应 16.0h， 以96%的产率得到5-benzo[1,3]dioxol-5-yl-2-methyl-3-styryl-2,3-dihydro-isoxazole-4-carboxylic acid ethyl ester
  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

• 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.