(4'R,4a'S,7a'R,12b'S)-9'-amino-3'-(cyclopropylmethyl)-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinolin]-4a'-ol | 263713-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (4'R,4a'S,7a'R,12b'S)-9'-amino-3'-(cyclopropylmethyl)-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinolin]-4a'-ol
• CAS: 263713-05-9
• 化学式: C₂₂H₂₈N₂O₄
• 分子量: 384.475
• InChiKey: KINLVAIXLSZYHV-RZXSNQJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  77.18
• 氢给体数：
  2.0
• 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)-9'-amino-3'-(cyclopropylmethyl)-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinolin]-4a'-ol 在 盐酸 、 TEA 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-[(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a-hydroxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl]methanesulfonamide
  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：

  纳曲酮 在 palladium on activated charcoal 盐酸 、 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 2-甲基-2-硝基丙烷 、 TEA 、 氢气 、 对甲苯磺酸 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 苯 为溶剂， 65.0 ℃ 、133.32 Pa 条件下， 反应 5.0h， 生成 (4'R,4a'S,7a'R,12b'S)-9'-amino-3'-(cyclopropylmethyl)-1',2',3',4',5',6'-hexahydro-4a'H,7a'H-spiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinolin]-4a'-ol
  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+