7-Methoxy-6-benzyloxy-1-benzyl-2-methyl-1,2,3,4-tetrahydro-isochinolin | 55161-46-1

• 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: 7-Methoxy-6-benzyloxy-1-benzyl-2-methyl-1,2,3,4-tetrahydro-isochinolin
• 英文别名: 1-benzyl-6-benzyloxy-7-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinoline；1-benzyl-7-methoxy-2-methyl-6-phenylmethoxy-3,4-dihydro-1H-isoquinoline
• CAS: 55161-46-1
• 化学式: C₂₅H₂₇NO₂
• 分子量: 373.495
• InChiKey: MNYDYTBKWLQSFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-Methoxy-6-benzyloxy-1-benzyl-2-methyl-1,2,3,4-tetrahydro-isochinolin 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到1-benzyl-6-hydroxy-7-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Preparation of dopaminergic N -alkyl-benzyltetrahydro-isoquinolines using a ‘one-pot’ procedure in acid medium

  摘要：

  The preparation of N-methyl-BTHIQ (4) from N-phenylethyl-phenacetamide (1) by cyclization, reduction and N-alkylation in acid medium has been achieved in good yield in a 'one-pot' procedure. Acylation of imine (2) intermediate afforded the Z and E stereoselectivity in the enamide formation. 6-Hydroxy-BTHIQ (7) shows selectivity for D-2 dopamine receptors, while its N-methylated homologue (8) displays higher affinities for both D-1 and D-2 receptor types, with an unexpected increase in D1 dopamine receptor affinity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00027-4
• 作为产物：
  描述：

  N-(3-benzyloxy-4-methoxyphenylethyl) phenylacetamide 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 37.0h， 生成 7-Methoxy-6-benzyloxy-1-benzyl-2-methyl-1,2,3,4-tetrahydro-isochinolin
  参考文献：
  名称：

  Preparation of dopaminergic N -alkyl-benzyltetrahydro-isoquinolines using a ‘one-pot’ procedure in acid medium

  摘要：

  The preparation of N-methyl-BTHIQ (4) from N-phenylethyl-phenacetamide (1) by cyclization, reduction and N-alkylation in acid medium has been achieved in good yield in a 'one-pot' procedure. Acylation of imine (2) intermediate afforded the Z and E stereoselectivity in the enamide formation. 6-Hydroxy-BTHIQ (7) shows selectivity for D-2 dopamine receptors, while its N-methylated homologue (8) displays higher affinities for both D-1 and D-2 receptor types, with an unexpected increase in D1 dopamine receptor affinity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00027-4