(4R,4aS,7R,7aR,12bS)-3-benzyl-2'-(hydroxymethyl)-9-methoxyspiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,5'-2H-1,3-oxazole]-4a-ol | 1415642-86-2

• 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: (4R,4aS,7R,7aR,12bS)-3-benzyl-2'-(hydroxymethyl)-9-methoxyspiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,5'-2H-1,3-oxazole]-4a-ol
• CAS: 1415642-86-2
• 化学式: C₂₇H₃₀N₂O₅
• 分子量: 462.546
• InChiKey: JLPXOSNMSQRXIC-MCEFUCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,4aS,7R,7aR,12bS)-3-benzyl-2'-(hydroxymethyl)-9-methoxyspiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,5'-2H-1,3-oxazole]-4a-ol 在 丙烷-1-硫醇 、 camphor-10-sulfonic acid 、 potassium tert-butylate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1'R,4R,4'R,4aS,7S,7'R,7aR,12bS)-3-benzylspiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,3'-2,5,8-trioxa-10-azatricyclo[5.2.1.04,10]decane]-4a,9-diol
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. 3: Synthesis of novel triplet drugs with the bis(epoxymethano) or bis(dimethylepoxymethano) structure (double-capped triplet)

  摘要：

  Novel double-capped triplet drugs, which have one pharmacophore unit and two epoxymethano or dimethylepoxymethano structures (termed cap or diMe-cap structures, respectively) were synthesized. Key intermediate oxazoline 16 derived from acetone enabled the effective synthesis of double-capped triplets. SYK-134 (7a) and SYK-135 (8a) with N-cyclopropylmethyl substituent and cap structures showed selectivities for the kappa opioid receptor. On the other hand, the N-Me series exhibited selectivities for the mu opioid receptor. The double-capped triplet drugs with diMe-cap structures preferred the mu receptor independently of their N-substituents. SYK-385 (19b), one of the mu-selective double-capped triplet drugs, showed the highest selectivity for the mu receptor among the reported mu-selective nonpeptide ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.023
• 作为产物：
  描述：

  17-N-benzyl-3-methoxynaltrexone 在 sodium acetate 、 potassium carbonate 、 氯化铵 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 生成 (4R,4aS,7R,7aR,12bS)-3-benzyl-2'-(hydroxymethyl)-9-methoxyspiro[2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,5'-2H-1,3-oxazole]-4a-ol
  参考文献：
  名称：

  Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. 3: Synthesis of novel triplet drugs with the bis(epoxymethano) or bis(dimethylepoxymethano) structure (double-capped triplet)

  摘要：

  Novel double-capped triplet drugs, which have one pharmacophore unit and two epoxymethano or dimethylepoxymethano structures (termed cap or diMe-cap structures, respectively) were synthesized. Key intermediate oxazoline 16 derived from acetone enabled the effective synthesis of double-capped triplets. SYK-134 (7a) and SYK-135 (8a) with N-cyclopropylmethyl substituent and cap structures showed selectivities for the kappa opioid receptor. On the other hand, the N-Me series exhibited selectivities for the mu opioid receptor. The double-capped triplet drugs with diMe-cap structures preferred the mu receptor independently of their N-substituents. SYK-385 (19b), one of the mu-selective double-capped triplet drugs, showed the highest selectivity for the mu receptor among the reported mu-selective nonpeptide ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.023