1-benzyl-6-hydroxy-7-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline | 16552-78-6

• 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-hydroxy-7-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-benzyl-6-hydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline；6-Hydroxy-7-methoxy-1-benzyl-2-methyl-1,2,3,4-tetrahydro-isochinolin；1-Benzyl-1,2,3,4-tetrahydro-6-hydroxy-7-methoxy-2-methyl-isochinolin；1-benzyl-7-methoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol；1-benzyl-7-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-6-ol
• CAS: 16552-78-6
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: BGMDDUWFRCOZHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-6-hydroxy-7-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline 在 potassium tert-butylate 作用下， 以 丙酮 、 叔丁醇 为溶剂， 反应 53.0h， 生成 trans-4-Hydroxy-5-methoxy-2-<2-(N-methyl-N-p-nitrobenzylamino)ethyl>stilbene
  参考文献：
  名称：

  Conversion of tetrahydroisoquinolinium salts into benzazepines

  摘要：

  DOI：

  10.1021/jo00178a001
• 作为产物：
  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

文献信息

• Studies on tetrahydroisoquinolines. XXVI. A biomimetic synthesis of 5-oxygenated 1,2,3,4-tetrahydroisoquinolines.
  作者：HIROSHI HARA、AKIRA TSUNASHIMA、HIROSHI SHINOKI、TOSHIFUMI AKIBA、OSAMU HOSHINO、BUNSUKE UMEZAWA

  DOI：10.1248/cpb.34.66

  日期：——

  Treatment with acetic anhydride-conc. sulufuric acid of o-quinol acetates (7, 11, 18, 19, 20, 28 and 34), which were derived from the corresponding 6-hydroxy-7-methoxytetrahydroisoquinolines (6, 12, 15, 16, 17, 27 and 31), gave the 5, 6-diacetates (8, 13, 21, 22, 23, 29 and 33, respectively). The diacetates were transformed into the corresponding 5, 6, 7-trimethoxytetrahydroisoquinolines (10, 14, 24, 25, 26, 30 and 32) by hydrolysis and subsequent methylation.

  用乙酸酐-缩合舒氟酸处理由相应的 6-羟基-7-甲氧基四氢异喹啉（6、12、15、16、17、27 和 31）衍生的邻喹啉乙酸酯（7、11、18、19、20、28 和 34），可得到 5、6-二乙酸酯（分别为 8、13、21、22、23、29 和 33）。通过水解和随后的甲基化，这些二乙酸酯被转化为相应的 5、6、7-三甲氧基四氢异喹啉（10、14、24、25、26、30 和 32）。
• Studies on tetrahydroisoquinolines. XXXII. Conversion of 7-hydroxy-6-methoxytetrahydroisoquinolines to 6-hydroxy-7-methoxytetrahydroisoquinolines.
  作者：HIROSHI HARA、TOSHIFUMI AKIBA、TAKANORI MIYASHITA、OSAMU HOSINO、BUNSUKE UMEZAWA

  DOI：10.1248/cpb.36.3638

  日期：——

  The 7-hydroxy-6-methoxytetrahydroisoquinolines (2 and 8) were transformed to the corresponding 6-hydroxy-7-methoxytetrahydroisoquinolines (4 and 14) via the p-quinol acetates (1 and 9), the p-quinol ethers (3a or 3b, and 10a), and the 6-alkoxy-7-ols (5 or 7, and 13), respectively.

  7-羟基-6-甲氧基四氢异喹啉（2和8）分别通过对-喹啉乙酸酯（1和9）、对-喹啉醚（3a或3b和10a）和6-烷氧基-7-醇（5或7和13）转化为相应的6-羟基-7-甲氧基四氢异喹啉（4和14）。
• A novel ring cleavage and recyclization of N-cyanomethyl-1,2,3,4-tetrahydroisoquinolinium methiodides: A biomimetic synthesis of litebamine
  作者：Hiroshi Hara、Ken-ichi Kaneko、Masaki Endoh、Hideharu Uchida、Osamu Hoshino

  DOI：10.1016/0040-4020(95)00614-e

  日期：1995.9

  Treatment of N-cyanomethyl-6-hydroxy-1,2,3,4-tetrahydroisoquinolinium methiodide (1) with NaOMe in MeOH caused C1-N fission and simultaneous recyclization to give 8-hydroxy-5-methoxymethyl-1,2,3,4-tetrahydroisoquinoline (2). By using of the rearrangement synthesis of litebamine (4) was carried out.
• SMITH, S. ,, JR;ELANGO, V.;SHAMMA, M., J. ORG. CHEM., 1984, 49, N 4, 581-586
  作者：SMITH, S. ,, JR、ELANGO, V.、SHAMMA, M.

  DOI：——

  日期：——
• HARA, HIROSHI;AKIBA, TOSHIFUMI;MIYASHITA, TAKANORI;HOSHINO, OSAMU;UMEZAWA+, CHEM. AND PHARM. BULL., 36,(1988) N 9, C. 3638-3641
  作者：HARA, HIROSHI、AKIBA, TOSHIFUMI、MIYASHITA, TAKANORI、HOSHINO, OSAMU、UMEZAWA+

  DOI：——

  日期：——