(R)-8-(benzyloxy)-5-(2-((5,6-diethyl-2-methyl-2,3-dihydro-1H-inden-2-yl)amino)-1-hydroxyethyl)quinolin-2(1H)-one | 312754-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (R)-8-(benzyloxy)-5-(2-((5,6-diethyl-2-methyl-2,3-dihydro-1H-inden-2-yl)amino)-1-hydroxyethyl)quinolin-2(1H)-one
• CAS: 312754-19-1
• 化学式: C₃₂H₃₆N₂O₃
• 分子量: 496.649
• InChiKey: YJIVFHSKCHABDP-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  74.35
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-8-(benzyloxy)-5-(2-((5,6-diethyl-2-methyl-2,3-dihydro-1H-inden-2-yl)amino)-1-hydroxyethyl)quinolin-2(1H)-one 在 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以98%的产率得到5-[(R)-2-(5,6-diethyl-2-methyl-indan-2-yl-amino)-1-hydroxy-ethyl]-8-hydroxy-1H-quinolin-2-one
  参考文献：
  名称：

  An investigation into the structure–activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol

  摘要：

  The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the beta(2)-adrenoceptor identified the 3,4-dihydroquinolinone and 5-n-butylindanyl analogues to demonstrate the most similar profiles to indacaterol. An alpha-methyl aminoindane analogue was discovered to be 25-fold more potent than indacaterol, and functional studies revealed an atypical beta(2)-adrenoceptor activation profile for this compound consistent with that of a slowly dissociating 'super agonist'. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.096
• 作为产物：
  描述：

  N-(5-acetyl-2-methyl-indan-2-yl)-benzamide 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 10% Pd/C 、 氢气 作用下， 以 四氢呋喃 、 硝基甲烷 、 乙醇 、 正丁醇 为溶剂， 25.0~100.0 ℃ 、101.33 kPa 条件下， 反应 166.25h， 生成 (R)-8-(benzyloxy)-5-(2-((5,6-diethyl-2-methyl-2,3-dihydro-1H-inden-2-yl)amino)-1-hydroxyethyl)quinolin-2(1H)-one
  参考文献：
  名称：

  An investigation into the structure–activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol

  摘要：

  The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the beta(2)-adrenoceptor identified the 3,4-dihydroquinolinone and 5-n-butylindanyl analogues to demonstrate the most similar profiles to indacaterol. An alpha-methyl aminoindane analogue was discovered to be 25-fold more potent than indacaterol, and functional studies revealed an atypical beta(2)-adrenoceptor activation profile for this compound consistent with that of a slowly dissociating 'super agonist'. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.096