4-[4-(3,4-Dimethoxy-phenyl)-5-(4-methoxy-phenyl)-pyridin-2-yl]-butan-1-ol | 184221-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-[4-(3,4-Dimethoxy-phenyl)-5-(4-methoxy-phenyl)-pyridin-2-yl]-butan-1-ol
• 英文别名: 4-[4-(3,4-Dimethoxyphenyl)-5-(4-methoxyphenyl)pyridin-2-yl]butan-1-ol
• CAS: 184221-16-7
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: KWPPRBVQHDCQIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[4-(3,4-Dimethoxy-phenyl)-5-(4-methoxy-phenyl)-pyridin-2-yl]-butan-1-ol 在 sodium tetrahydroborate 、 甲基磺酰氯 、 三乙胺 作用下， 生成 2-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-1,6,7,8,9,9a-hexahydro-4H-quinolizin-4-one
  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：

  2-(1-Chloro-ethyl)-4-(3,4-dimethoxy-phenyl)-5-(4-methoxy-phenyl)-pyridine 在 盐酸 、 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 48.5h， 生成 4-[4-(3,4-Dimethoxy-phenyl)-5-(4-methoxy-phenyl)-pyridin-2-yl]-butan-1-ol
  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.