(E)-5-(3,4-Dimethoxy-phenyl)-pent-4-ene-2,3-dione | 184220-92-6

• 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: (E)-5-(3,4-Dimethoxy-phenyl)-pent-4-ene-2,3-dione
• 英文别名: (E)-5-(3,4-dimethoxyphenyl)pent-4-ene-2,3-dione
• CAS: 184220-92-6
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: BLAPLNCZVXFLLY-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5-(3,4-Dimethoxy-phenyl)-pent-4-ene-2,3-dione 在 吡啶 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium 、 盐酸羟胺 、 potassium tert-butylate 、 二异丁基氢化铝 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 77.42h， 生成 (+/-)-septicine
  参考文献：
  名称：

  A Unified Strategy for the Synthesis of Phenanthroizidine Alkaloids:  Preparation of Sterically Congested Pyridines

  摘要：

  Total syntheses of the representative phenanthroizidine alkaloids, tylophorine and antofine, and of their seco congeners, septicine and julandine, have been completed from sterically congested 3,4-diarylpyridines prepared by a modified Knoevenagel-Stobbe synthesis. Central to the success of this effort was the ability of alpha-dicarbonyl enones to combine in a formal [4 + 2]-cycloaddition with sterically demanding vinyl ethers.

  DOI：

  10.1021/ja962757p
• 作为产物：
  描述：

  (E)-1-(3,4-Dimethoxy-phenyl)-4,4-dimethoxy-pent-1-en-3-one 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以76%的产率得到(E)-5-(3,4-Dimethoxy-phenyl)-pent-4-ene-2,3-dione
  参考文献：
  名称：

  A Unified Strategy for the Synthesis of Phenanthroizidine Alkaloids:  Preparation of Sterically Congested Pyridines

  摘要：

  Total syntheses of the representative phenanthroizidine alkaloids, tylophorine and antofine, and of their seco congeners, septicine and julandine, have been completed from sterically congested 3,4-diarylpyridines prepared by a modified Knoevenagel-Stobbe synthesis. Central to the success of this effort was the ability of alpha-dicarbonyl enones to combine in a formal [4 + 2]-cycloaddition with sterically demanding vinyl ethers.

  DOI：

  10.1021/ja962757p

文献信息

• A Unified Strategy for the Synthesis of Phenanthroizidine Alkaloids:  Preparation of Sterically Congested Pyridines
  作者：Marco A. Ciufolini、Frank Roschangar

  DOI：10.1021/ja962757p

  日期：1996.1.1

  Total syntheses of the representative phenanthroizidine alkaloids, tylophorine and antofine, and of their seco congeners, septicine and julandine, have been completed from sterically congested 3,4-diarylpyridines prepared by a modified Knoevenagel-Stobbe synthesis. Central to the success of this effort was the ability of alpha-dicarbonyl enones to combine in a formal [4 + 2]-cycloaddition with sterically demanding vinyl ethers.