delta 7-methylnaltrexone bromide | 1027638-96-5

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: delta 7-methylnaltrexone bromide
• 英文别名: N-Methyl 7,8-didehydronaltrexone Bromide (Mixture of Diastereomers, >90%)；(3R,4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one;bromide
• CAS: 1027638-96-5
• 化学式: Br*C₂₁H₂₄NO₄
• 分子量: 434.33
• InChiKey: PHHHFCWRROMSHI-NQMNLMSRSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.55
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  delta 7-methylnaltrexone bromide 在 甲酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 12.0h， 生成 (R)-methylnaltrexone bromide
  参考文献：
  名称：

  Synthesis of Naltrexone and (R)-Methylnaltrexone from Oripavine via Direct Oxidation of Its Quaternary Salts

  摘要：

  (R)-Methylnaltrexone and naltrexone were each prepared in four steps from oripavine in practical yields. The procedure involved quaternization of oripavine with cyclopropylmethyl halides, singlet oxygen oxidation of the quaternary salts, and the reduction of endo peroxides to 14-hydroxyketone functionalities. (R)-Methylnaltrexone was prepared from the corresponding R-diastereomer of the oripavine salt. All diastereomeric mixtures of the quaternary salts were subjected to N-demethylation with sodium thiolate to yield cyclopropyl methylnororipavine, which was converted into naltrexone by peracid oxidation and hydrogenation according to established procedures.

  DOI：

  10.1055/s-0034-1378808
• 作为产物：
  描述：

  在 甲酸 、 氢气 、 溴 、 氧气 、 tetraphenylporphyrin 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 5.0~15.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 delta 7-methylnaltrexone bromide
  参考文献：
  名称：

  Synthesis of Naltrexone and (R)-Methylnaltrexone from Oripavine via Direct Oxidation of Its Quaternary Salts

  摘要：

  (R)-Methylnaltrexone and naltrexone were each prepared in four steps from oripavine in practical yields. The procedure involved quaternization of oripavine with cyclopropylmethyl halides, singlet oxygen oxidation of the quaternary salts, and the reduction of endo peroxides to 14-hydroxyketone functionalities. (R)-Methylnaltrexone was prepared from the corresponding R-diastereomer of the oripavine salt. All diastereomeric mixtures of the quaternary salts were subjected to N-demethylation with sodium thiolate to yield cyclopropyl methylnororipavine, which was converted into naltrexone by peracid oxidation and hydrogenation according to established procedures.

  DOI：

  10.1055/s-0034-1378808

文献信息

• WO2008/64351
  申请人：——

  公开号：——

  公开（公告）日：——