17-(cyclobutylmethyl)-7,8-didehydro-4,5α-epoxymorphinan-3,6α,14-triol | 66944-73-8

• 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: 17-(cyclobutylmethyl)-7,8-didehydro-4,5α-epoxymorphinan-3,6α,14-triol
• 英文别名: nalbuphine；(4R,4aS,7S,7aR,12bS)-3-(cyclobutylmethyl)-1,2,4,7,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
• CAS: 66944-73-8
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: CDHIVLQVEOOANN-CEDHKZHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  17-(cyclobutylmethyl)-7,8-didehydro-4,5α-epoxymorphinan-6-keto-3,14-diol 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 二甲基亚砜 为溶剂， 以60.2%的产率得到17-(cyclobutylmethyl)-7,8-didehydro-4,5α-epoxymorphinan-3,6α,14-triol
  参考文献：
  名称：

  One-Pot Process for Synthesis of Nalbuphine Hydrochloride and Impurity Control Strategy

  摘要：

  An improved kilogram-scale process of synthesis of nalbuphine was developed by investigating the critical parameters. Ten process-related impurities were identified, of which the source and control strategy was elucidated. Moreover, tetramethylammonium triacetoxyborohydride (Me4NBH(OAc)(3)) was developed to reduce the imine and ketone in one pot. As a result, 6-beta-epimer was significantly controlled to only 0.08% in the crude nalbuphine. The improved process was robust at kilogram scale in 60.4% overall yield with 99.95% high-performance liquid chromatography (HPLC) purity.

  DOI：

  10.1021/acs.oprd.0c00321

文献信息

• LARGE SUBSTITUTENT, NON-PHENOLIC OPIOIDS AND METHODS OF USE THEREOF
  申请人：Rensselaer Polytechnic Institute

  公开号：US20160257677A1

  公开（公告）日：2016-09-08

  8-Substituted-2,6-methano-3-benzazocines of general structure are useful as analgesics, anti-diarrheal agents, anticonvulsants, antitussives and anti-addiction medications.