(+/-)-O-benzylpseudocodamine | 41182-99-4

• 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: (+/-)-O-benzylpseudocodamine
• 英文别名: 6,7-dimethoxy-1-[(3-methoxy-4-phenylmethoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinoline
• CAS: 41182-99-4
• 化学式: C₂₇H₃₁NO₄
• 分子量: 433.547
• InChiKey: BEDXOXVQZJHRPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-O-benzylpseudocodamine 在 iron(III) chloride on silica 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以40%的产率得到(±)-4-((6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-2-methoxyphenol
  参考文献：
  名称：

  Iron trichloride/silicon dioxide reacts as oxidant or Lewis acid with phenol ethers

  摘要：

  DOI：

  10.1021/jo00335a045
• 作为产物：
  描述：

  1-(4-(benzyloxy)-3-methoxybenzyl)-6,7-dimethoxyisoquinoline 在 sodium tetrahydroborate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (+/-)-O-benzylpseudocodamine
  参考文献：
  名称：

  Chemical modifications of the N -methyl-laudanosine scaffold point to new directions for SK channels exploration

  摘要：

  An asparagine or a histidine are present in a similar position in the outer pore region of SK2 and SK3 channels, respectively. Therefore, this structural difference was targeted in order to develop selective blockers of SK channel subtypes. Following docking investigations, based on theoretical models of truncated SK2 and SK3 channels, the benzyl side chain of N-methyl-laudanosine (NML) was functionalized in order to target this specific amino-acid residues. Chiral butanamide and benzyloxy analogues were prepared, resolved and tested for their affinity for SK2 and SK3 channels. Isoquinolinium (NMIQ) derivatives have a higher affinity for both SK channel subtypes than the corresponding derivative with no functionalized side chain. This trend was observed also for the 1,2,3,4-tetrahydroisoquinoline (THIQ) analogues. A benzyloxy functionalized NML enantiomer has a higher affinity than NML stereoisomers. Otherwise, the conserved affinity of these analogues led to the opportunity to further investigate in terms of possible labeling for in vivo investigations of the role of SK channels. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.083

文献信息

• The Efficient Synthesis of Morphinandienone Alkaloids by Using a Combination of Hypervalent Iodine(III) Reagent and Heteropoly Acid
  作者：Hiromi Hamamoto、Yukiko Shiozaki、Hisanori Nambu、Kayoko Hata、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1002/chem.200400358

  日期：2004.10.18

  The non-phenolic coupling reaction of benzyltetrahydroisoquinolines (laudanosine derivatives) by using a hypervalent iodine(III) reagent is described. In general, chemical oxidation of laudanosine gives glaucine. In contrast to general chemical oxidizing reagent systems, the novel use of reagent combination of phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) afforded morphinandienone

  描述了通过使用高价碘（III）试剂进行的苄基四氢异喹啉（月桂肌苷衍生物）的非酚偶联反应。通常，月桂肌苷的化学氧化产生青光氨酸。与一般的化学氧化试剂系统相比，苯基碘双（三氟乙酸盐）（PIFA）和杂多酸（HPA）试剂组合的新用途以极高的收率提供了吗啡酮。为了通过简单的反应步骤实现偶联反应，证明了使用硅胶负载的HPA代替HPA，并再次发挥了足够的收率。本试剂体系PIFA / HPA也被用于其他非酚苄基四氢异喹啉的氧化反应，并成功地转化为吗啡酮。
• JEMPTY, T. C.;GOGINS, K. A. Z.;MAZUR, Y.;MILLER, L. L., J. ORG. CHEM., 1981, 46, N 22, 4545-4551
  作者：JEMPTY, T. C.、GOGINS, K. A. Z.、MAZUR, Y.、MILLER, L. L.

  DOI：——

  日期：——