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(6S,7S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinane-6,7-diol | 160694-06-4

中文名称
——
中文别名
——
英文名称
(6S,7S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinane-6,7-diol
英文别名
——
(6S,7S,9S,13S)-8,14-Didehydro-4-(benzyloxy)-17-<(benzyloxy)carbonyl>-3,8-dimethoxymorphinane-6,7-diol化学式
CAS
160694-06-4
化学式
C33H35NO7
mdl
——
分子量
557.643
InChiKey
GZYWDKBYMRHVOB-OEGNNNOBSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    742.2±60.0 °C(Predicted)
  • 密度:
    1.35±0.1 g/cm3(Predicted)

反应信息

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文献信息

  • Syntheses of Antitumor Morphinane Alkaloids, Sinococuline and 6-epi-, 7-epi-, and 6-epi-7-epi-Sinococuline, from Sinomenine
    作者:Yukio Hitotsuyanagi、Kunihiko Nishimura、Hiroshi Ikuta、Koichi Takeya、Hideji Itokawa
    DOI:10.1021/jo00119a037
    日期:1995.7
    An antitumor alkaloid, sinococuline (1), and its C-6 and/or C-7 epimeric analogs 3-5 have been synthesized from sinomenine (2). The carbonyl transposition from 9 to 8 using selenoxide chemistry proceeded in an efficient manner. Successive C-6 hydroxylation through the potassium enolate oxidation with (-)-(2S,8aR)-(camphorsulfonyl)oxaziridine (23) predominantly produced the beta-hydroxy enone 7a, which allowed access to sinococuline (1) and the 7-epi-analog 4. On the contrary, the oxidation of the lithium enolate with (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine (22) resulted in predominant formation of the a-hydroxy enone 7b, which was converted to the 6-epi-analogs 3 and 5. In contrast to the marked antitumor activity of 1, analogs 3-5 showed no activity.
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