11β-[trans-3-(4-chlorophenyl)propenoyl]amino-11α-[cis-2-(methoxycarbonyl)ethenyl]-8-methoxy-3-methyl-1,2,3,4,5,6-hexahydro-6α,7-(methyleneoxy)-2,6-methano-3-benzazocine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 11β-[trans-3-(4-chlorophenyl)propenoyl]amino-11α-[cis-2-(methoxycarbonyl)ethenyl]-8-methoxy-3-methyl-1,2,3,4,5,6-hexahydro-6α,7-(methyleneoxy)-2,6-methano-3-benzazocine
• 英文别名: methyl (Z)-3-[(1R,10R,15S)-15-[[(E)-3-(4-chlorophenyl)prop-2-enoyl]amino]-5-methoxy-11-methyl-3-oxa-11-azatetracyclo[6.5.1.11,10.04,14]pentadeca-4,6,8(14)-trien-15-yl]prop-2-enoate
• 化学式: C₂₈H₂₉ClN₂O₅
• 分子量: 509.002
• InChiKey: UTRBHCFPSZFEGT-IJFYYPNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  蒂巴因 在 samarium diiodide 、 benzyltrimethylammonium periodate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 11β-[trans-3-(4-chlorophenyl)propenoyl]amino-11α-[cis-2-(methoxycarbonyl)ethenyl]-8-methoxy-3-methyl-1,2,3,4,5,6-hexahydro-6α,7-(methyleneoxy)-2,6-methano-3-benzazocine
  参考文献：
  名称：

  Selective Opening of Ring C in the Morphine Skeleton by an Unexpected Cleavage of the C5−C6 Bond in Cycloadducts of Thebaine and Acyl Nitroso Compounds

  摘要：

  [GRAPHICS]Acyl nitroso cycloadducts of the alkaloid thebaine undergo an unexpected cleavage of the C5-C6 bond when treated with 2 equiv of samarium(II) iodide in THF to give novel hexahydrobenzazocine products. A proposed mechanism for the transformation involves rearrangement of the initial radical anion.

  DOI：

  10.1021/jo052016j

文献信息

• Selective Opening of Ring C in the Morphine Skeleton by an Unexpected Cleavage of the C5−C6 Bond in Cycloadducts of Thebaine and Acyl Nitroso Compounds
  作者：Gary N. Sheldrake、Nicolas Soissons

  DOI：10.1021/jo052016j

  日期：2006.1.1

  [GRAPHICS]Acyl nitroso cycloadducts of the alkaloid thebaine undergo an unexpected cleavage of the C5-C6 bond when treated with 2 equiv of samarium(II) iodide in THF to give novel hexahydrobenzazocine products. A proposed mechanism for the transformation involves rearrangement of the initial radical anion.