7,8-didehydro-4,5-epoxy-17-methylmorphinan-2,6-diyl bis(naphthalene-1-carboxylate) | 633700-75-1

• 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: 7,8-didehydro-4,5-epoxy-17-methylmorphinan-2,6-diyl bis(naphthalene-1-carboxylate)
• 英文别名: morphine bis(1-naphthoate)；Morphine di-(naphthalene-1-carboxylate)；[(4R,4aR,7S,7aR,12bS)-3-methyl-9-(naphthalene-1-carbonyloxy)-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] naphthalene-1-carboxylate
• CAS: 633700-75-1
• 化学式: C₃₉H₃₁NO₅
• 分子量: 593.679
• InChiKey: OKMGZRBUYJWHFL-PLZSVQQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  magnesium monoperoxyphthalate hexahydrate 、 7,8-didehydro-4,5-epoxy-17-methylmorphinan-2,6-diyl bis(naphthalene-1-carboxylate) 以 甲醇 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  使用非经典的Polonovski反应进一步研究叔胺生物碱的N-去甲基化作用。

  摘要：

  铁盐介导的Polonovski反应有效地将某些鸦片生物碱N-去甲基化。在该方法中，据报道使用叔N-甲基氧化胺的盐酸盐可以得到更好的所需N-脱甲基化产物的产率。在本文中，我们报告了在铁盐介导的Polonovski反应中使用N-氧化物盐的进一步研究。还描述了一种去除铁盐的有效方法，该方法极大地促进了N-nor产物的分离和纯化。

  DOI：

  10.1016/j.bmcl.2006.03.017
• 作为产物：
  描述：

  1-萘甲酰氯 、 吗啡 以 吡啶 为溶剂， 反应 20.0h， 生成 7,8-didehydro-4,5-epoxy-17-methylmorphinan-2,6-diyl bis(naphthalene-1-carboxylate)
  参考文献：
  名称：

  Inter- and intramolecular C—H...π interactions in morphine bis(1-naphthoate)

  摘要：

  The crystal structure of morphine bis(1-naphthoate) [ or 7,8-didehydro-4,5-epoxy-17-methylmorphinan- 2,6-diyl bis(naphthalene-1-carboxylate)], C39H31NO5, determined at 123 K, shows extensive C-H ...pi interactions in the crystal lattice. Of particular interest is an intramolecular C - H ...pi interaction within the unit cell between the two naphthoyl groups. Comparison of the opiate scaffolds of morphine bis( 1-naphthoate) and morphine shows only a small increase in strain due to the steric bulk of the naphthoyl groups. The crystal packing shows distinct areas of packing for the naphthalene/aromatic groups and the opiate backbone. Extensive inter- and intramolecular C - H...pi interactions lead to a densely packed aromatic region in the crystal lattice.

  DOI：

  10.1107/s0108270103015622

文献信息

• Inter- and intramolecular C—H...π interactions in morphine bis(1-naphthoate)
  作者：Nicholas Gathergood、Peter J. Scammells、Gary D. Fallon

  DOI：10.1107/s0108270103015622

  日期：2003.9.15

  The crystal structure of morphine bis(1-naphthoate) [ or 7,8-didehydro-4,5-epoxy-17-methylmorphinan- 2,6-diyl bis(naphthalene-1-carboxylate)], C39H31NO5, determined at 123 K, shows extensive C-H ...pi interactions in the crystal lattice. Of particular interest is an intramolecular C - H ...pi interaction within the unit cell between the two naphthoyl groups. Comparison of the opiate scaffolds of morphine bis( 1-naphthoate) and morphine shows only a small increase in strain due to the steric bulk of the naphthoyl groups. The crystal packing shows distinct areas of packing for the naphthalene/aromatic groups and the opiate backbone. Extensive inter- and intramolecular C - H...pi interactions lead to a densely packed aromatic region in the crystal lattice.
• Further investigation of the N-demethylation of tertiary amine alkaloids using the non-classical Polonovski reaction
  作者：Shanti Thavaneswaran、Peter J. Scammells

  DOI：10.1016/j.bmcl.2006.03.017

  日期：2006.6

  iron salt-mediated Polonovski reaction efficiently N-demethylates certain opiate alkaloids. In this process, the use of the hydrochloride salt of the tertiary N-methyl amine oxide was reported to give better yields of the desired N-demethylated product. Herein, we report further investigation into the use of N-oxide salts in the iron salt-mediated Polonovski reaction. An efficient approach for the

  铁盐介导的Polonovski反应有效地将某些鸦片生物碱N-去甲基化。在该方法中，据报道使用叔N-甲基氧化胺的盐酸盐可以得到更好的所需N-脱甲基化产物的产率。在本文中，我们报告了在铁盐介导的Polonovski反应中使用N-氧化物盐的进一步研究。还描述了一种去除铁盐的有效方法，该方法极大地促进了N-nor产物的分离和纯化。