[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1R)-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate | 1026632-76-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1R)-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate
• CAS: 1026632-76-7
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: IVUAINLZGBJGPG-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1R)-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 [(1R)-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-yl]methanol
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m
• 作为产物：
  描述：

  5,6-二甲氧基-1,2,3,4-四氢1-萘酮 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 草酰氯 、 二甲基十二/十四烷基叔胺 、 N,N-二甲基甲酰胺 、 zinc(II) iodide 作用下， 以 乙醇 、 乙二醇 、 甲苯 为溶剂， 反应 27.5h， 生成 [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1R)-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m