1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | 3423-37-8

• 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-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-Benzyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isochinolin；6,7-Dimethoxy-1-benzyl-1,2,3,4-tetrahydro-isochinolin
• CAS: 3423-37-8
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: HWNSTGWDEVWFNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 sodium pentanolate 作用下， 以 戊醇 、 氯仿 为溶剂， 反应 3.0h， 生成 (1R)-1,2,3,4-tetrahydro-1-benzoyl-6,7-dimethoxyisoquinoline
  参考文献：
  名称：

  Optically active tetrahydro-.alpha.-phenyl-6,7-dimethoxyisoquinoline-1-methanols from (1-phenylethyl)ureas. Absolute configuration of (-)- and (+)-isomers of the erythro series

  摘要：

  DOI：

  10.1021/jo00274a044
• 作为产物：
  描述：

  1-Benzyl-6,7-dimethoxy-3,4-dihydro-isochinolin; Hydrochlorid 在 盐酸 、 水 、 锌 作用下， 生成 1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Autonomic Blocking Agents. I. Branched Aliphatic Quaternary Ammonium and Analogous Cyclic Ammonium Salts

  摘要：

  DOI：

  10.1021/jo50006a014

文献信息

• Development of Pd(OAc)2-catalyzed tandem oxidation of C N, C C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids
  作者：Saeko Nishimoto、Hiromichi Nakahashi、Masahiro Toyota

  DOI：10.1016/j.tetlet.2020.152599

  日期：2020.12

  A catalytic tandem oxidation of CN, CC, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine

  开发了C N，CC和C（sp 3）–H键的催化串联氧化反应。该串联氧化被应用于罂粟碱和普洛西汀A的两步全合成。另外，通过应用该催化串联氧化，从高哌啶醇和2-溴苯基乙腈的六步合成实现了鹅绒den碱的全合成。此外，木糖精以76％的产率直接转化为8-氧伪伪巴马汀证明了该催化反应的多功能性。
• Oxidation of 1-benzyldihydroisoquinolines or 1-benzyltetrahydroisoquinolines with dioxygen to 1-benzoylisoquinolines
  作者：Haifeng Gan、Yunyu Lu、Yue Huang、Lijun Ni、Jinyi Xu、Hequan Yao、Xiaoming Wu

  DOI：10.1016/j.tetlet.2011.01.058

  日期：2011.3

  An environmental-benign methodology to synthesize 1-benzoylisoquinolines from 1-benzyl-3, 4-dihydroisoquinolines or 1-benzyl-1,2,3,4-tetrahydroisoquinolines using dioxygen as an oxidant was developed. This methodology in combination with Bischler-Napieralski reaction leads to a facile synthesis of 1-benzoylisoquinolines from phenylacetic acids and phenylethanamines.

  开发了一种环境友好的方法，使用双氧作为氧化剂从1-苄基-3，4-二氢异喹啉或1-苄基1,2,3,4-四氢异喹啉合成1-苯甲酰基异喹啉。这种方法与Bischler-Napieralski反应结合可以从苯乙酸和苯乙胺中轻松合成1-苯甲酰基异喹啉。
• Synthesis of Benzoazocines from Substituted Tetrahydroisoquinolines and Activated Alkynes in a Tetrahydropyridine Ring Expansion
  作者：Leonid G. Voskressensky、Anna V. Listratova、Tatiana N. Borisova、Grigoriy G. Alexandrov、Alexey V. Varlamov

  DOI：10.1002/ejoc.200700602

  日期：2007.12

  Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  四氢异喹啉在乙腈或甲醇中存在活化炔烃的情况下经历串联哌啶环扩大，以高产率生产四氢苯并[d]偶氮辛。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• SAR studies of capsazepinoid bronchodilators. Part 2: Chlorination and catechol replacement in the A-ring
  作者：Magnus Berglund、María F. Dalence-Guzmán、Staffan Skogvall、Olov Sterner

  DOI：10.1016/j.bmc.2007.11.061

  日期：2008.3

  airways. From a systematic variation of the capsazepine structure, divided into four regions, SARs were established. This paper concerns the chlorination of the A-ring as well as the replacement of the catechol with bioisosteric groups. It is revealed that chlorination of the A-ring has a profound effect on activity. Moreover, di-chlorination of the 6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline structure

  辣椒素及其衍生物和类似物是人类小气道收缩的一般抑制剂。从辣椒素结构的系统变化分为四个区域，建立了SAR。本文涉及A环的氯化以及生物等位基团取代邻苯二酚。揭示了A环的氯化对活性有深远的影响。此外，与卡塞平相比，对6,7-二羟基-1,2,3,4-四氢异喹啉结构进行二氯化处理会导致效力增加10倍。
• Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- and 7-membered C-ring homologues
  作者：Hiroaki Kurouchi

  DOI：10.1039/d0ob02096f

  日期：——

  A route to the direct amidation of aromatic-ring-tethered N-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate

  开发了直接酰胺化芳族环系N-氨基甲酰基四氢异喹啉底物的途径。该途径使人们能够普遍获得8-氧小ber碱及其5和7元C环同系物。它克服了导致异喹啉主链破坏的不希望的串联副反应，这种副反应在我们先前报道的超酸性氨基甲酸酯活化方法下不可避免地发生。