9,17-dibromo-10-methoxyvincamine methyl ether | 154375-75-4

• 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: 9,17-dibromo-10-methoxyvincamine methyl ether
• CAS: 154375-75-4
• 化学式: C₂₃H₂₈Br₂N₂O₄
• 分子量: 556.294
• InChiKey: TYCFEGFTVHUPIL-SKWRMQMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  52.93
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  9,17-dibromo-10-methoxyvincamine methyl ether 在 jones reagent 作用下， 以36%的产率得到9,17-dibromo-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
• 作为产物：
  描述：

  10-bromoapovincamine 在 2,4,6-三甲基吡啶 、 copper(l) iodide 、 高氯酸 、 溴 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 9,17-dibromo-10-methoxyvincamine 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.