3-methoxy-2-{[(2E)-3-phenylprop-2-en-1-yl]oxy}benzaldehyde | 133495-64-4

• 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: 3-methoxy-2-{[(2E)-3-phenylprop-2-en-1-yl]oxy}benzaldehyde
• 英文别名: 3-methoxy-2-[(E)-3-phenylprop-2-enoxy]benzaldehyde
• CAS: 133495-64-4
• 化学式: C₁₇H₁₆O₃
• mdl: MFCD04054574
• 分子量: 268.312
• InChiKey: OXLZMGXXXHJDMZ-RMKNXTFCSA-N

物化性质

• 沸点：
  449.6±40.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-methoxy-2-{[(2E)-3-phenylprop-2-en-1-yl]oxy}benzaldehyde 在 sodium ethanolate 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 19.0h， 生成 (Z)-2-Diphenylvinylideneamino-3-[3-methoxy-2-((E)-3-phenyl-allyloxy)-phenyl]-acrylic acid ethyl ester
  参考文献：
  名称：

  Domino reactions. One-pot preparation of fluoreno[2,3,4-ij]isoquinoline derivatives from conjugated ketene imines

  摘要：

  Iminophosphoranes 4, derived from ethyl alpha-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160-degrees-C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/second ring closure/double aromatization process to give isoquinoline derivatives 7 and/or the previously unknown fluoreno[2,3,4-ij]isoquinolines 9 in moderate yields. Similarly, iminophosphoranes 14 derived from ethyl alpha-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160-degrees-C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.

  DOI：

  10.1021/jo00012a039
• 作为产物：
  描述：

  邻香草醛 、 Cinnamyl bromide 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以71%的产率得到3-methoxy-2-{[(2E)-3-phenylprop-2-en-1-yl]oxy}benzaldehyde
  参考文献：
  名称：

  Domino reactions. One-pot preparation of fluoreno[2,3,4-ij]isoquinoline derivatives from conjugated ketene imines

  摘要：

  Iminophosphoranes 4, derived from ethyl alpha-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160-degrees-C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/second ring closure/double aromatization process to give isoquinoline derivatives 7 and/or the previously unknown fluoreno[2,3,4-ij]isoquinolines 9 in moderate yields. Similarly, iminophosphoranes 14 derived from ethyl alpha-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160-degrees-C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.

  DOI：

  10.1021/jo00012a039

文献信息

• MOLINA, PEDRO;ALAJARIN, MATEO;VIDAL, ANGEL;FENAU-DUPONT, J.;DECLERQ, J. P+, J. ORG. CHEM., 56,(1991) N2, C. 4008-4016
  作者：MOLINA, PEDRO、ALAJARIN, MATEO、VIDAL, ANGEL、FENAU-DUPONT, J.、DECLERQ, J. P+

  DOI：——

  日期：——
• Domino reactions. One-pot preparation of fluoreno[2,3,4-ij]isoquinoline derivatives from conjugated ketene imines
  作者：Pedro Molina、Mateo Alajarin、Angel Vidal、J. Fenau-Dupont、J. P. Declerq

  DOI：10.1021/jo00012a039

  日期：1991.6

  Iminophosphoranes 4, derived from ethyl alpha-azido-2-(allyloxy)-3-methoxycinnamates, react with ketenes to give the corresponding ketene imines, which by thermal treatment at 150-160-degrees-C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/second ring closure/double aromatization process to give isoquinoline derivatives 7 and/or the previously unknown fluoreno[2,3,4-ij]isoquinolines 9 in moderate yields. Similarly, iminophosphoranes 14 derived from ethyl alpha-azido-2,3-disubstituted-4-(allyloxy)cinnamates reacted with diphenyl ketene to give the intermediate ketene imines, which at 150-160-degrees-C undergo a cascade of pericyclic reactions to give the isoquinolines 15 and the pentacyclic compounds 16 in moderate yields.