5-(3-benzyloxy-4-methoxy-benzyl)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline | 108017-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5-(3-benzyloxy-4-methoxy-benzyl)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline
• 英文别名: 5-(3-Benzyloxy-4-methoxy-benzyl)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isochinolin；5-[(4-methoxy-3-phenylmethoxyphenyl)methyl]-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
• CAS: 108017-85-2
• 化学式: C₂₆H₂₇NO₄
• 分子量: 417.505
• InChiKey: RNOIYRSJJQEXJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-benzyloxy-4-methoxy-benzyl)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 在 甲烷 、 palladium dichloride 氢气 作用下， 以 甲醇 为溶剂， 反应 3.5h， 以53.9%的产率得到(+/-)-1-(3-hydroxy-4-methoxybenzyl)-1,2,3,4-tetrahydro-2-methyl-6,7-methylenedioxyisoquinoline
  参考文献：
  名称：

  Synthesis of some 1-(3-hydroxy-4-methoxybenzyl)-2-alkyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolines and their binding affinities to DA receptor subtypes

  摘要：

  1-(3-Hydroxy-4-methoxybenzyl)-2-alkyl-6,7-methylenedioxytetrahydroisoquinolines (3a-c), derived from the D-1 selective antagonist S-bulbocapnine by cleavage of the bond between the 2 aromatic moieties, have been synthesized and their in vitro affinity towards D-1 and D-2 receptors evaluated. Of the compounds tested, the 2-methyl derivative 3a while showing poor affinity towards D-1 receptors was able to inhibit the D-2 radioligand H-3-raclopride binding by 60% at 10(-5) M. Conformational analysis allows reasonable explanations of the loss of D-1-affinity of 3a with respect to the model.

  DOI：

  10.1016/0223-5234(94)90126-0
• 作为产物：
  描述：

  (3-苄氧基-4-甲氧基-苯基)乙酸 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 、 甲苯 、 xylene 为溶剂， 反应 21.7h， 生成 5-(3-benzyloxy-4-methoxy-benzyl)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline
  参考文献：
  名称：

  Synthesis of some 1-(3-hydroxy-4-methoxybenzyl)-2-alkyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolines and their binding affinities to DA receptor subtypes

  摘要：

  1-(3-Hydroxy-4-methoxybenzyl)-2-alkyl-6,7-methylenedioxytetrahydroisoquinolines (3a-c), derived from the D-1 selective antagonist S-bulbocapnine by cleavage of the bond between the 2 aromatic moieties, have been synthesized and their in vitro affinity towards D-1 and D-2 receptors evaluated. Of the compounds tested, the 2-methyl derivative 3a while showing poor affinity towards D-1 receptors was able to inhibit the D-2 radioligand H-3-raclopride binding by 60% at 10(-5) M. Conformational analysis allows reasonable explanations of the loss of D-1-affinity of 3a with respect to the model.

  DOI：

  10.1016/0223-5234(94)90126-0