methyl (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'-carboxylate | 263713-10-6

• 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: methyl (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'-carboxylate
• CAS: 263713-10-6
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: PXPDMYZHCJQPPJ-PPRPKMEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (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'-carboxylate 在 盐酸 、 2-甲基-2-硝基丙烷 、 TEA 、 一水合肼 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 2.0h， 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：

  4,5α-epoxy-3,14-dihydroxy-17-methylmorphinan-6-spiro-2'-(1,3-dioxolane) 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 TEA 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 methyl (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'-carboxylate
  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+