[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (6R)-2,3,6,7,8,9-hexahydrobenzo[g][1]benzofuran-6-carboxylate | 1026481-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (6R)-2,3,6,7,8,9-hexahydrobenzo[g][1]benzofuran-6-carboxylate
• CAS: 1026481-77-5
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: XZYRNPRURCEUSC-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (6R)-2,3,6,7,8,9-hexahydrobenzo[g][1]benzofuran-6-carboxylate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 [(R)-1-(2,3,6,7,8,9-Hexahydro-naphtho[1,2-b]furan-6-yl)methyl]-methyl-amine
  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-溴-2,3-二氢苯并呋喃 在 palladium on activated charcoal 氢氧化钾 、 sodium tetrahydroborate 、 三氯化铝 、 草酰氯 、 二甲基十二/十四烷基叔胺 、 锂丁酯 、 氢气 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙二醇 、 甲苯 、 苯 为溶剂， -30.0~100.0 ℃ 、405.3 kPa 条件下， 反应 49.58h， 生成 [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (6R)-2,3,6,7,8,9-hexahydrobenzo[g][1]benzofuran-6-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