6β-Methyleneoxynaloxon | 55096-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 6β-Methyleneoxynaloxon
• 英文别名: 17-allyl-4,5α-epoxy-(6βO)-spiro[morphinane-6,2'-oxirane]-3,14-diol；Spiro[7aH-8,9c-(iminoethano)phenanthro[4,5-bcd]furan-5(4aH),2a(2)-oxirane]-3,7a-diol, 6,7,8,9-tetrahydro-12-(2-propenyl)-, (2a(2)S,4aR,7aS,8R,9cS)-；(4R,4aS,7S,7aR,12bS)-3-prop-2-enylspiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,2'-oxirane]-4a,9-diol
• CAS: 55096-32-7
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: OAQKXONKAIKPDF-GIOXJEDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.46
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  纳洛酮 、 trimethyloxosulfonium chloride 生成 6β-Methyleneoxynaloxon
  参考文献：
  名称：

  Narcotic antagonists. 4. Carbon-6 derivatives of N-substituted noroxymorphones as narcotic antagonists

  摘要：

  A series of new narcotic antagonists has been synthesized by modifying the C-6 carbonyl group in naloxone (Ia) and naltrexone (Ib). New functional units were introduced by reaction with various phosphorus and sulfur ylides and alkyllithium reagents. The activity of the new compounds were measured by the hot-plate and tail-clip tests after oral administration to mice. The majority of the new narcotic antagonists exhibited oral potencies considerably superior to the parent compounds, with 6-methylene derivatives IIa and IIb showing the most impressive increases.

  DOI：

  10.1021/jm00237a008