3-[4-(3,4-dimethoxyphenyl)-5-(4-methoxyphenyl)pyridin-2-yl]propan-1-ol | 184221-11-2

• 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: 3-[4-(3,4-dimethoxyphenyl)-5-(4-methoxyphenyl)pyridin-2-yl]propan-1-ol
• CAS: 184221-11-2
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: GFQWWRPALPOCLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  3-[4-(3,4-dimethoxyphenyl)-5-(4-methoxyphenyl)pyridin-2-yl]propan-1-ol 在 sodium tetrahydroborate 、 甲基磺酰氯 、 三乙胺 作用下， 生成 7-(3,4-dimethoxyphenyl)-6-(4-methoxyphenyl)-1,2,3,5,8,8a-hexahydroindolizine
  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 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.42h， 生成 3-[4-(3,4-dimethoxyphenyl)-5-(4-methoxyphenyl)pyridin-2-yl]propan-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 Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine‐Resistant <i>Plasmodium falciparum</i>
  作者：Naoto Yamasaki、Ikumi Iwasaki、Kazu Sakumi、Rei Hokari、Aki Ishiyama、Masato Iwatsuki、Masataka Nakahara、Shuhei Higashibayashi、Takeshi Sugai、Hiroshi Imagawa、Miwa Kubo、Yoshiyasu Fukuyama、Satoshi Ōmura、Hirofumi Yamamoto

  DOI：10.1002/chem.202100032

  日期：2021.3.22

  reaction of easily accessible 3,5‐dichloro‐2H‐1,4‐oxazin‐2‐one with 14 a as a key step. Furthermore, it is demonstrated that dehydroantofine is a promising candidate as a new antimalarial agent in a biological assay with chloroquine‐resistant Plasmodium falciparum.

  通过采用新颖的区域选择性氮杂杂Diels-Alder反应（可轻松获得的3,5-二氯-2 H -1,4-恶嗪-2-1与14 a为关键步骤）实现了脱氢黄嘌呤的总合成。此外，在抗氯喹抗性恶性疟原虫的生物检测中，证明了脱氢黄嘌呤是一种有前途的候选药物，可作为一种新型抗疟药。
• 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.