(2RS,4aSR,8aRS)-decahydronaphthalen-2-ylamine | 936-35-6

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2RS,4aSR,8aRS)-decahydronaphthalen-2-ylamine
• 英文别名: (+/-)-(4ar,8ac)-decahydro-[2t]naphthylamine；(+/-)-(4ar,8ac)-Decahydro-[2t]naphthylamin；(+/-)-2t-Amino-(4arH.8acH)-decahydro-naphthalin；Decahydro-[2]naphthylamin；(2R,4aS,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-amine
• CAS: 936-35-6；1196-54-9；3922-10-9；18649-65-5；23017-71-2
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: FFROQSBSJYRALS-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2RS,4aSR,8aRS)-decahydronaphthalen-2-ylamine 在 4 A molecular sieve 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 正戊烷 为溶剂， 反应 169.25h， 生成
  参考文献：
  名称：

  Novel Hexahydrospiro[piperidine-4,1‘-pyrrolo[3,4-c]pyrroles]:  Highly Selective Small-Molecule Nociceptin/Orphanin FQ Receptor Agonists

  摘要：

  Novel hexahydrospiro[piperidine-4,1'-pyrrolo[3,4-c]pyrroles that act as potent and selective orphanin FQ/nociceptin (N/OFQ) receptor (NOP) agonists were identified. The best compound, (+)-5a, potently inhibited H-3-N/OFQ binding to the NOP receptor (K-i = 0.49 nM) but was > 1000-fold less potent in binding to MOP, KOP, and DOP opiate receptors. Further, (+)-5a potently stimulated GTPgammaS binding to NOP membranes (EC50 = 65 nM) and inhibited forskolin-mediated cAMP accumulation in NOP-expressing cells (EC50 = 9.1 nM) with a potency comparable to that of the natural peptide agonist N/OFQ. These results indicate that (+)-5a is a highly selective and potent small-molecule full agonist of the NOP receptor.

  DOI：

  10.1021/jm0209174
• 作为产物：
  描述：

  (2RS,4aSR,8aRS)-benzyl(decahydronaphthalen-2-yl)amine 在 10percent Pd/C 氢气 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以99%的产率得到(2RS,4aSR,8aRS)-decahydronaphthalen-2-ylamine
  参考文献：
  名称：

  Novel Hexahydrospiro[piperidine-4,1‘-pyrrolo[3,4-c]pyrroles]:  Highly Selective Small-Molecule Nociceptin/Orphanin FQ Receptor Agonists

  摘要：

  Novel hexahydrospiro[piperidine-4,1'-pyrrolo[3,4-c]pyrroles that act as potent and selective orphanin FQ/nociceptin (N/OFQ) receptor (NOP) agonists were identified. The best compound, (+)-5a, potently inhibited H-3-N/OFQ binding to the NOP receptor (K-i = 0.49 nM) but was > 1000-fold less potent in binding to MOP, KOP, and DOP opiate receptors. Further, (+)-5a potently stimulated GTPgammaS binding to NOP membranes (EC50 = 65 nM) and inhibited forskolin-mediated cAMP accumulation in NOP-expressing cells (EC50 = 9.1 nM) with a potency comparable to that of the natural peptide agonist N/OFQ. These results indicate that (+)-5a is a highly selective and potent small-molecule full agonist of the NOP receptor.

  DOI：

  10.1021/jm0209174

文献信息

• Hueckel, Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 1
  作者：Hueckel

  DOI：——

  日期：——
• Hueckel, Justus Liebigs Annalen der Chemie, 1938, vol. 533, p. 20
  作者：Hueckel

  DOI：——

  日期：——
• Tardella,P.A.; Pellacani,L., Gazzetta Chimica Italiana, 1973, vol. 103, p. 337 - 343
  作者：Tardella,P.A.、Pellacani,L.

  DOI：——

  日期：——
• The cis-Decahydro-2-naphthoic Acids and their Relationship to the cis-2-Decalols and cis-2-Decalylamines
  作者：William G. Dauben、Earl Hoerger

  DOI：10.1021/ja01148a027

  日期：1951.4