(4'R,4a'S,7a'R,12b'S)-4a'-hydroxy-3'-methyl-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-9'-carbonyl azide | 263713-12-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (4'R,4a'S,7a'R,12b'S)-4a'-hydroxy-3'-methyl-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-9'-carbonyl azide
• CAS: 263713-12-8
• 化学式: C₂₀H₂₂N₄O₅
• 分子量: 398.418
• InChiKey: MORWAHPJBXAHGT-CODKJTEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  116.99
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4'R,4a'S,7a'R,12b'S)-4a'-hydroxy-3'-methyl-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-9'-carbonyl azide 在 TEA 作用下， 以 苯 为溶剂， 生成 benzyl ((4'R,4a'S,7a'R,12b'S)-4a'-hydroxy-3'-methyl-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinolin]-9'-yl)carbamate
  参考文献：
  名称：

  Investigation of Phenolic Bioisosterism in Opiates:  3-Sulfonamido Analogues of Naltrexone and Oxymorphone

  摘要：

  The phenolic hydroxy group of opiate-derived ligands is of known importance for biological activity. On the basis of its putative role as a hydrogen-bonding donor in the interaction with opioid receptors, it was replaced with a sulfonamide group because of their similar pK(a) values. The first thebaine-derived 3-amino (8a, 8b) and subsequent sulfonamide analogues (10a, 10b) were synthesized from naltrexone (la) and oxymorphone (1b) in a linear nine-step synthesis. The sulfonamides were tested in vitro and found inactive.

  DOI：

  10.1021/ol005561+
• 作为产物：
  描述：

  (4'R,4a'S,7a'R,12b'S)-4a'-hydroxy-3'-methyl-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-9'-carbohydrazide 在 盐酸 、 2-甲基-2-硝基丙烷 作用下， 以 四氢呋喃 、 水 为溶剂， 以92%的产率得到(4'R,4a'S,7a'R,12b'S)-4a'-hydroxy-3'-methyl-2',3',4',4a',5',6'-hexahydro-1'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-9'-carbonyl azide
  参考文献：
  名称：

  Investigation of Phenolic Bioisosterism in Opiates:  3-Sulfonamido Analogues of Naltrexone and Oxymorphone

  摘要：

  The phenolic hydroxy group of opiate-derived ligands is of known importance for biological activity. On the basis of its putative role as a hydrogen-bonding donor in the interaction with opioid receptors, it was replaced with a sulfonamide group because of their similar pK(a) values. The first thebaine-derived 3-amino (8a, 8b) and subsequent sulfonamide analogues (10a, 10b) were synthesized from naltrexone (la) and oxymorphone (1b) in a linear nine-step synthesis. The sulfonamides were tested in vitro and found inactive.

  DOI：

  10.1021/ol005561+