1-benzyl-6-benzyloxy-7-methoxy-1,2,3,4-tetrahydro-isoquinoline | 47545-34-6

• 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: 1-benzyl-6-benzyloxy-7-methoxy-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 1-benzyl-7-methoxy-6-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 47545-34-6
• 化学式: C₂₄H₂₅NO₂
• 分子量: 359.468
• InChiKey: CEXJLJZSVFHBKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-6-benzyloxy-7-methoxy-1,2,3,4-tetrahydro-isoquinoline 在 盐酸 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 33.0h， 生成 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 15.0h， 生成 1-benzyl-6-benzyloxy-7-methoxy-1,2,3,4-tetrahydro-isoquinoline
  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

文献信息

• Synthesis of N-diisopropyl phosphoryl benzyl-tetrahydroisoquinoline, a new class of mitochondrial complexes I and III inhibitors
  作者：Inmaculada Andreu、Nuria Cabedo、José R Tormo、Almudena Bermejo、Rossella Mello、Diego Cortes

  DOI：10.1016/s0960-894x(00)00262-6

  日期：2000.7

  The synthesis of N-(O,O-diisopropyl phosphoryl)-benzyltetrahydroisoquinoline (3) has been achieved in a 'one pot' procedure From imine (2) and diisopropyl-phosphorochloridate (1) generated in situ (POCl3 + iPrOH). Compound 3 is the first benzyltetrahydroisoquinoline derivative found to be a potent inhibitor of mitochondrial complexes I and III, and therefore it opens a new perspective with this series of compounds as they can be considered as new class of antitumor agents. (C) 2000 Elsevier Science Ltd. All rights reserved.