10-methoxy-6-oxovincamine methyl ether | 154375-78-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Eburnan型生物碱
• 英文名称: 10-methoxy-6-oxovincamine methyl ether
• CAS: 154375-78-7
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: XZKJJMHTJRPUGG-PUHATCMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  70.0
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  10-methoxy-6-oxovincamine methyl ether 在 盐酸 、 mercury(II) diacetate 作用下， 以38%的产率得到6-hydroxy-10-methoxy-py-tetrahydroapovincamine chloride
  参考文献：
  名称：

  Synthesis of Potential Cytotoxic Quaternary Ammoniums by Oxidation of Eburnane Alkaloids

  摘要：

  Oxidation of vincamine and substituted analogs on ring-A was carried out in two steps: benzylic oxidation by Jones reagent and aromatization of ring-C with Hg(OAc)(2) or TI(OCOCF3)(3) in trifluoroacetic acid. Final compounds are quaternary ammoniums which exhibited weak cytotoxicity or no cytotoxicity according to substituents on ring-A and nature of ring-E.

  DOI：

  10.3987/com-93-6481
• 作为产物：
  描述：

  10-bromoapovincamine 在 platinum(IV) oxide 、 palladium on activated charcoal 2,4,6-三甲基吡啶 、 copper(l) iodide 、 高氯酸 、 jones reagent 、 氢气 、 溴 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~120.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 10-methoxy-6-oxovincamine methyl ether
  参考文献：
  名称：

  Synthesis of Potential Cytotoxic Quaternary Ammoniums by Oxidation of Eburnane Alkaloids

  摘要：

  Oxidation of vincamine and substituted analogs on ring-A was carried out in two steps: benzylic oxidation by Jones reagent and aromatization of ring-C with Hg(OAc)(2) or TI(OCOCF3)(3) in trifluoroacetic acid. Final compounds are quaternary ammoniums which exhibited weak cytotoxicity or no cytotoxicity according to substituents on ring-A and nature of ring-E.

  DOI：

  10.3987/com-93-6481

文献信息

• Synthesis of Potential Cytotoxic Quaternary Ammoniums by Oxidation of Eburnane Alkaloids
  作者：Guy Lewin、Corinne Schaeffer、Alain Pierr�、Nicolas Guilbaud、Ghanem Atassi、Jacques Poisson

  DOI：10.3987/com-93-6481

  日期：——

  Oxidation of vincamine and substituted analogs on ring-A was carried out in two steps: benzylic oxidation by Jones reagent and aromatization of ring-C with Hg(OAc)(2) or TI(OCOCF3)(3) in trifluoroacetic acid. Final compounds are quaternary ammoniums which exhibited weak cytotoxicity or no cytotoxicity according to substituents on ring-A and nature of ring-E.