19-[trans-3-(4-chlorophenyl)propenoyl]-6,14-dihydro-6β,14β-epoxyiminothebaine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 19-[trans-3-(4-chlorophenyl)propenoyl]-6,14-dihydro-6β,14β-epoxyiminothebaine
• 英文别名: (E)-3-(4-chlorophenyl)-1-[(1S,2R,6R,14R,15R)-11,15-dimethoxy-5-methyl-13,16-dioxa-5,17-diazahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,18-tetraen-17-yl]prop-2-en-1-one
• 化学式: C₂₈H₂₇ClN₂O₅
• 分子量: 506.986
• InChiKey: GPSUPZCHTSUQES-OCDVTGHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  19-[trans-3-(4-chlorophenyl)propenoyl]-6,14-dihydro-6β,14β-epoxyiminothebaine 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以65%的产率得到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
• 作为产物：
  描述：

  蒂巴因 、 (E)-3-(4-chlorophenyl)-N-hydroxyacrylamide 在 benzyltrimethylammonium periodate 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到19-[trans-3-(4-chlorophenyl)propenoyl]-6,14-dihydro-6β,14β-epoxyiminothebaine
  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.