4,5α-epoxy-3-methoxy-17,17-dimethyl-6-oxo-morphinanium; iodide | 6451-17-8

• 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: 4,5α-epoxy-3-methoxy-17,17-dimethyl-6-oxo-morphinanium; iodide
• 英文别名: 4,5α-Epoxy-3-methoxy-17,17-dimethyl-6-oxo-morphinanium; Jodid；(4R,4aR,7aR,12bS)-9-methoxy-3,3-dimethyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one;iodide
• CAS: 6451-17-8
• 化学式: C₁₉H₂₄NO₃*I
• 分子量: 441.309
• InChiKey: KMPZYQYWUKNGEX-KMZNWEMKSA-M

物化性质

• 熔点：
  255 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5α-epoxy-3-methoxy-17,17-dimethyl-6-oxo-morphinanium; iodide 在 sodium tetrahydroborate 、 双氧水 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 生成 (1R,5S,14S)-14-(2-hydroxyethyl)-11-methoxy-15-oxatetracyclo[10.2.1.05,14.08,13]pentadeca-6,8(13),9,11-tetraen-2-ol
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753
• 作为产物：
  描述：

  二氢可待因酮 、 碘甲烷 以 乙醇 为溶剂， 反应 20.0h， 生成 4,5α-epoxy-3-methoxy-17,17-dimethyl-6-oxo-morphinanium; iodide
  参考文献：
  名称：

  Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

  摘要：

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

  DOI：

  10.1021/jo3026753

文献信息

• Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity
  作者：Robert D. Giacometti、Jan Duchek、Lukas Werner、Afeef S. Husni、Christopher R. McCurdy、Stephen J. Cutler、D. Phillip Cox、Tomas Hudlicky

  DOI：10.1021/jo3026753

  日期：2013.4.5

  Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.