6β-amino-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3-ol | 107819-73-8

• 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: 6β-amino-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3-ol
• 英文别名: (4R,4aR,7R,7aR,12bS)-7-amino-3-(cyclopropylmethyl)-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
• CAS: 107819-73-8
• 化学式: C₂₀H₂₆N₂O₂
• 分子量: 326.439
• InChiKey: VEWKAIPTRLIJRB-VYCUNPCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-4-chloro-4-oxo-2-butenoate 、 6β-amino-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3-ol 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以25%的产率得到(E)-4-<<17-(cyclopropylmethyl)-4,5α-epoxy-3-hydroxymorphinan-6β-yl>amino>-4-oxo-2-butenoic acid methyl ester
  参考文献：
  名称：

  Nonequilibrium opioid antagonist activity of 6,14-dideoxynaltrexone derivatives

  摘要：

  A series of 6,14-dideoxynaltrexones that contain different electrophiles in the 6-position were synthesized and evaluated for nonequilibrium opioid antagonist activity in the guinea pig ileum and mouse vas deferens preparations. Members 3-5 of the series possessed irreversible antagonist activity profiles similar to those previously reported for the 14-hydroxy analogues. In contrast, the 14-deoxy-beta-funaltrexamine (14-deoxy-beta-FNA) analogue (6) exhibited a profile of irreversible antagonist activity that differed from that of beta-FNA. It was concluded that the 14-hydroxy group is not essential for irreversible blockage when the electrophile is capable of reacting with a broad spectrum of nucleophiles. However, with a highly selective electrophile such as the fumarate group, the 14-hydroxy function appears to play a role in aligning the molecule to optimize attack by a receptor-based nucleophile.

  DOI：

  10.1021/jm00389a014
• 作为产物：
  描述：

  3-O-acetyl-N-cyclopropylmethylnormorphine 在 palladium on activated charcoal 盐酸羟胺 、 氢气 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 苯 为溶剂， 反应 0.17h， 生成 6β-amino-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3-ol
  参考文献：
  名称：

  光信反应在吗啡化合物中的应用。6β-氨基吗啡和可待因衍生物的制备

  摘要：

  摘要 通过Mitsunobu反应合成了几种新的7 8 6β-氨基吗啡和可待因衍生物，在C环上带有一个Δ7,8双键。这些化合物的催化氢化为合成相应的 6β-氨基-二氢类似物提供了一种新的立体选择性方法。饱和和不饱和氨基化合物的环 C 的不同构象允许研究构效关系，并且通过不饱和衍生物的氚化可以检查底物 - 受体相互作用。

  DOI：

  10.1080/00397919208020855

文献信息

• Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac
  作者：Csaba Simon、Sándor Hosztafi、Sándor Makleit

  DOI：10.1016/s0040-4020(01)85541-1

  日期：1994.1

  As a continuation of our work, aimed at adopting the Mitsunobu reaction in the morphine series, a few representatives of dihydroisocodeines and dihydroisomorphines and their 14 beta-hydroxy analogues were prepared. p-Nitrobenzoic acid was used as carboxylic acid and the prepared esters were cleaved to obtain the title compounds. Using phthalimide as acidic component several new 6 beta-phthalimidodihydromorphine and dihydrocodeine derivatives and their 14 beta-hydroxy analogues have been synthesized. Cleavage of the phthalimido derivatives with hydrazine hydrate afforded the corresponding 6 beta-amino derivatives.