N,8α-ethano-19(R)-n-butynorthevinol | 110222-26-9

• 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: N,8α-ethano-19(R)-n-butynorthevinol
• 英文别名: (2R)-2-[(1S,7R,8R,9R,12S,13R,21R)-9,18-dimethoxy-20-oxa-4-azaheptacyclo[13.6.1.01,12.04,13.07,12.09,21.019,22]docosa-10,15(22),16,18-tetraen-8-yl]hexan-2-ol
• CAS: 110222-26-9
• 化学式: C₂₈H₃₇NO₄
• 分子量: 451.606
• InChiKey: DFBOPVDKSWRUAQ-KQEBYZDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N,8α-ethano-19(R)-n-butynorthevinol 在 丙烷-1-硫醇 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以70%的产率得到N,8α-ethano-19(R)-n-butylnororvinol
  参考文献：
  名称：

  Nitrogen-bridged conformationally constrained etorphine analogs. Synthesis and biological evaluation

  摘要：

  Three N-C8-bridged analogues 4-6 of the opiate etorphine (3) were synthesized and evaluated for opiate agonism and antagonism. In each case ring closure was effected by intramolecular N-alkylation with a suitably developed C8 side chain. Another key synthetic step was the selective monoprotection of diol 11, which allowed independent elaborations of the C7 and C8 side chains. All three analogues showed distinctly diminished agonist activities when compared to the corresponding N-methyl compound, 19(R)-n-butylorvinol (3). Furthermore, no antagonist activity was detectable. The results demonstrate that the conformation at the amino nitrogen in rigid morphinans is critical for potent opiate activity.

  DOI：

  10.1021/jm00394a016
• 作为产物：
  描述：

  N-benzoylnorthebaine 在 盐酸 、 溴丁基-镁 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 四溴化碳 、 potassium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 193.03h， 生成 N,8α-ethano-19(R)-n-butynorthevinol
  参考文献：
  名称：

  Nitrogen-bridged conformationally constrained etorphine analogs. Synthesis and biological evaluation

  摘要：

  Three N-C8-bridged analogues 4-6 of the opiate etorphine (3) were synthesized and evaluated for opiate agonism and antagonism. In each case ring closure was effected by intramolecular N-alkylation with a suitably developed C8 side chain. Another key synthetic step was the selective monoprotection of diol 11, which allowed independent elaborations of the C7 and C8 side chains. All three analogues showed distinctly diminished agonist activities when compared to the corresponding N-methyl compound, 19(R)-n-butylorvinol (3). Furthermore, no antagonist activity was detectable. The results demonstrate that the conformation at the amino nitrogen in rigid morphinans is critical for potent opiate activity.

  DOI：

  10.1021/jm00394a016

文献信息

• MAURER, PETER J.;RAPOPORT, HENRY, J. MED. CHEM., 30,(1987) N 11, 2016-2026
  作者：MAURER, PETER J.、RAPOPORT, HENRY

  DOI：——

  日期：——