2-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinolinium bromide | 5096-82-2

• 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: 2-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinolinium bromide
• 英文别名: benzyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium hydrobromide；2-benzyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium bromide；Isoquinolinium, 3,4-dihydro-6,7-dimethoxy-2-(phenylmethyl)-, bromide；2-benzyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2-ium;bromide
• CAS: 5096-82-2
• 化学式: Br*C₁₈H₂₀NO₂
• 分子量: 362.266
• InChiKey: FFPQJPZLRDFYPA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinolinium bromide 在 氢氧化钾 、 三甲基氯硅烷 、 potassium tert-butylate 、 氨 、 sodium 、 silver nitrate 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 45.5h， 生成 扎替雷定
  参考文献：
  名称：

  Silver nitrate-promoted ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives: application to the synthesis of the anti-anginal zatebradine

  摘要：

  The one step AgNO3-mediated ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives into 1,2-dihydro- and 1,2,3,4-tetrahydro-benzo[d]azepin-2-ones, respectively, is reported. This reaction offers a convenient entry to potentially active substances such as the anti-anginal zatebradine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00919-5
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉 以89的产率得到2-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinolinium bromide
  参考文献：
  名称：

  Tetrahedron Lett. 2003, 44, 4203-4206

  摘要：

  DOI：

文献信息

• A Mild and Chemoselective Reduction of Cyclic Iminium Salts
  作者：Giovanni Palmisano、Giordano Lesma、Micaela Nali、Bruno Rindone、Stefano Tollari

  DOI：10.1055/s-1985-31434

  日期：——

  N-Substituted cyclic iminium salts are conveniently reduced to the corresponding tertiary amines in good yields by reaction with tributylstannane in methanol at room temperature. A variety of functional groups (such as ketonic groups) present in the molecule are not affected under these conditions.

  在室温下，通过与甲醇中的三丁基锡烷反应，N-取代环状亚胺盐可以方便地还原成相应的叔胺，而且收率很高。在这些条件下，分子中存在的各种官能团（如酮基）不会受到影响。
• A facile synthesis of novel polycyclic spiropyrrolidine oxindoles incorporating the 1,3-dipolar cycloaddition of azomethine ylides
  作者：Krisztina E. Treuerne Balázs、Márk Molnár、Zoltán Madarász、Miklós Nyerges

  DOI：10.1080/00397911.2020.1799011

  日期：2020.11.1

  Abstract This study describes the synthesis of novel polycyclic spiropyrrolidine oxindoles through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ with 3-(arylmethylene)-indolin-2-ones. Effect of substituents of azomethine ylides and various dipolarophiles on reactivity, as well as on the products regio- and stereoselectivity was investigated. Graphical Abstract

  摘要 本研究描述了通过 3-(芳基亚甲基)-indolin-2-ones 原位生成的偶氮甲碱叶立德的 1,3-偶极环加成反应合成新型多环螺吡咯烷羟吲哚。研究了偶氮甲碱叶立德和各种偶极试剂的取代基对反应性以及产物区域和立体选择性的影响。图形概要
• A stereocontrolled synthesis of (.+-.)-emetine and (.+-.)-protoemetinol by intramolecular michael reaction.
  作者：YOSHIRO HIRAI、TAKASHI TERADA、ATSUSHI HAGIWARA、TAKAO YAMAZAKI

  DOI：10.1248/cpb.36.1343

  日期：——

  An intramolecular Michael reaction of 9 stereoselectively gave the tricyclic compound (10), which was converted to (±)-protoemetinol (2) and 13. Compound 13 is an important intermediate for the synthesis of (±)-emetine. A simpler preparation of 13 was also carried out by the intramolecular Michael reaction of 14, followed by reduction of the ketone moietv. Furthermore, the stereoselective formation of 26, which is an intermediate for the synthesis of (±)-emetine, was achieved by the floowing sequence of reactions : intramolecular Michael reaction, of the ketone moiety, and removal of the N-carbomethoxy group.

  9 的分子内迈克尔反应立体选择性地生成了三环化合物 (10)，然后转化为 (±)-protoemetinol (2) 和 13。化合物 13 是合成(±)-美丁的重要中间体。通过 14 的分子内迈克尔反应，然后还原酮莫埃特 v，也可以更简单地制备 13。此外，通过以下反应顺序：分子内迈克尔反应、酮基反应和去除 N-甲酰甲氧基反应，立体选择性地生成了 26，它是合成(±)-甜菜碱的中间体。
• New reactions of 3,4‐dihydro‐6,7‐dimethoxyisoquinoline ylide with nitrile derivatives
  作者：Márk Molnár、Krisztina E. Treuerne Balázs、Zoltán Madarász、Miklós Nyerges

  DOI：10.1002/jhet.4496

  日期：2022.9

  Novel examples for dipolar cycloaddition of isoquinolinium ylides to nitriles leading to new imidazo[2,1-a]isoquinolines were described and the potential of this reaction in synthetic chemistry was explored. As a by-product of this research, a number of N-substituted, 3,4-dihydro-1H-isoquinoline-1-carbonitriles were synthesized by a simple, efficient reaction of a series of isoquinolinium bromides

  描述了异喹啉叶立德与腈的偶极环加成产生新的咪唑并[2,1- a ]异喹啉的新例子，并探索了该反应在合成化学中的潜力。作为本研究的副产品，通过一系列异喹啉溴化物和氰基甲酸乙酯在存在下进行简单、高效的反应，合成了许多N-取代的 3,4-二氢-1 H-异喹啉-1-甲腈。三乙胺。
• Novel zinc-promoted alkylation of iminium salts. New synthesis of benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids and related compounds
  作者：Tatsuya Shono、Hiroshi Hamaguchi、Manji Sasaki、Shumei Fujita、Kimihiko Nagami

  DOI：10.1021/jo00158a010

  日期：1983.5