(1R,3R)-N-benzyl-6-hydroxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline | 218956-26-4

• 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: (1R,3R)-N-benzyl-6-hydroxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: (1R,3R)-2-benzyl-1,3-dimethyl-8-propan-2-yloxy-3,4-dihydro-1H-isoquinolin-6-ol
• CAS: 218956-26-4
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: JOHFWRJBSSHQHK-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (1R,3R)-N-benzyl-6-hydroxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 甲酸 、 三正丁胺 、 1,2-二溴四氯乙烷 、 1,3-双(二苯基膦)丙烷 、 三氟化硼 、 氢气 、 sodium acetate 、 thallium (I) ethoxide 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， -40.0~100.0 ℃ 、101.33 kPa 条件下， 反应 10.5h， 生成 N-formyldioncophylline C
  参考文献：
  名称：

  First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C

  摘要：

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10301-5
• 作为产物：
  描述：

  (1R,3R)-N-benzyl-6-methoxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline 在 sodium thioisopropylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以68%的产率得到(1R,3R)-N-benzyl-6-hydroxy-8-isopropoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C

  摘要：

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10301-5

文献信息

• First Atropo-Divergent Total Synthesis of the Antimalarial Korupensamines A and B by the “Lactone Method”
  作者：Gerhard Bringmann、Michael Ochse、Roland Götz

  DOI：10.1021/jo991634v

  日期：2000.4.1

  configurationally stable P-diol 10a or, optionally, the M-product 10b. From the axially chiral phenylisoquinolines thus obtained atropo-diastereodivergently, the authentic natural naphthylisoquinolines with the respective axial configurations, korupensamines A (1a) and B (1b), were obtained by completion of the second naphthalene ring, starting from the previous "bridgehead" C1 unit.

  描述了通过“内酯法”的应用，抗疟疾中的甲氨蝶呤胺A（1a）和B（1b）的立体选择性全合成。首次对5,8'-偶联的萘基异喹啉生物碱进行阻转性选择的关键步骤是酯8的区域选择性分子内偶联，以得到结构不稳定的内酯桥联的联芳基9及其对阻转异构体的选择性裂解，具有多种手性和非手性H -亲核试剂，产生构型稳定的P-二醇10a或任选的M产物10b。从由此获得的轴向手性苯基异喹啉，通过对位-非对映异构，通过完成第二个萘环获得了具有各自轴向构型的天然天然萘基异喹啉，即甲氨苯胺A（1a）和B（1b），从先前的“
• The Atropo-Divergent Preparation of Axially Chiral Biaryls Through the `Lactone Methodology': Total Synthesis of Korupensamine B
  作者：Gerhard Bringmann

  DOI：10.1055/s-1998-1912

  日期：1998.11
• First synthesis of the antimalarial naphthylisoquinoline alkaloid dioncophylline C, and its unnatural anti-HIV dimer, jozimine C
  作者：Gerhard Bringmann、Jörg Holenz、Ralf Weirich、Martin Rübenacker、Christian Funke、Michael R. Boyd、Robert J. Gulakowski、Guido François

  DOI：10.1016/s0040-4020(97)10301-5

  日期：1998.1

  The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved.