N-Methoxyquinaldinium perchlorate | 61704-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-Methoxyquinaldinium perchlorate
• 英文别名: Quinolinium, 1-methoxy-2-methyl-, perchlorate；1-methoxy-2-methylquinolin-1-ium;perchlorate
• CAS: 61704-03-8
• 化学式: C₁₁H₁₂NO*ClO₄
• 分子量: 273.673
• InChiKey: BZYNSXXOVDHENU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.26
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Methoxyquinaldinium perchlorate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 4-叔丁基-2-甲基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  tert-Butylation of Quinolinium Cations and Quinoline N-Oxides by tert-Butylmercury Halides

  摘要：

  In the presence of t-BuHgCl/KI the radical cations formed by the addition of tert-butyl radicals to C-2 of the quinolinium cation react in Me(2)SO by proton loss followed by one-electron oxidation (1a, R = H, Me, Cl). For the N-methyl, or N-methoxyquinolinium cations proton loss is not observed and the radical cations react by one-electron reduction (1b, R = Me, Cl; Ic, R = Me), With quinoline N-oxide and its 4-substituted derivatives the C-2 adduct radicals (1d, R = H, Me, Cl) are deprotonated by DABCO to yield after one-electron oxidation the 2-tert-butylquinoline N-oxides. The adduct radical cations formed by t-Bu(.) addition at the C-4 of quinolinium ions 2 seldom lose the C-4 proton but react by reduction, hydration, or in the case of 2-chloroquinoline N-oxide, dimerization. The loss of the proton from the 2-adducts 1 but not from the 4-adducts 2 seems to be stereoelectronic in origin. With N-methylquinolinium cation the addition of t-Bu(.) occurs selectively (>90%) at C-4 in contrast to the low selectivity observed in addition to quinolinium ion itself. However, with N-methoxyquinolinium perchlorate the major reaction products (70-90%) result from the addition of t-Bu(.) at C-2.

  DOI：

  10.1021/jo00122a013
• 作为产物：
  描述：

  2-甲基喹啉N-氧化物 、 硫酸二甲酯 在 高氯酸 、 乙醇 作用下， 反应 2.0h， 以73%的产率得到N-Methoxyquinaldinium perchlorate
  参考文献：
  名称：

  具有正性肌力活性的化合物，IV：N-甲氧基喹啉盐的合成及其对心肌的影响

  摘要：

  N-Methoxyquinolinium salts 3 通过烷基化相应的 N-氧化物 2 制备，作为潜在的强心剂，由两种不同的方法合成。1. 使用 30% H2O2 或 3-氯过苯甲酸氧化某些喹啉衍生物 1。2. 喹啉 - N - 氧化物 2a、2c 和 2m 的硝化。2h 和 2k 的制备需要随后的硝基亲核同位取代。测试化合物3对来自豚鼠的离体左心房和乳头肌的正性肌力活性。构效关系表明，该效应取决于目标化合物的 N-甲氧基以及吸电子取代基的存在。

  DOI：

  10.1002/ardp.19933260410

文献信息

• Compounds with Positive Inotropic Activity, IV: Synthesis of N-Methoxyquinolinium Salts and Their Effects in Heart Muscles
  作者：Claudia Bünz、Dieter Heber、Ursula Ravens

  DOI：10.1002/ardp.19933260410

  日期：——

  3 are prepared as potential cardiotonic agents by alkylation of the corresponding N‐oxides 2 synthesized by two different methods. 1. Oxidation of some quinoline derivatives 1 using 30% H2O2 or 3‐chloroperbenzoic acid. 2. Nitration of the quinoline‐N‐oxides 2a, 2c, and 2m. Preparation of 2h and 2k requires subsequent nucleophilic ipso‐substitution of the nitro group. The compounds 3 are tested for

  N-Methoxyquinolinium salts 3 通过烷基化相应的 N-氧化物 2 制备，作为潜在的强心剂，由两种不同的方法合成。1. 使用 30% H2O2 或 3-氯过苯甲酸氧化某些喹啉衍生物 1。2. 喹啉 - N - 氧化物 2a、2c 和 2m 的硝化。2h 和 2k 的制备需要随后的硝基亲核同位取代。测试化合物3对来自豚鼠的离体左心房和乳头肌的正性肌力活性。构效关系表明，该效应取决于目标化合物的 N-甲氧基以及吸电子取代基的存在。
• tert-Butylation of Quinolinium Cations and Quinoline N-Oxides by tert-Butylmercury Halides
  作者：Glen A. Russell、Lijuan Wang、Ching-Fa Yao

  DOI：10.1021/jo00122a013

  日期：1995.9

  In the presence of t-BuHgCl/KI the radical cations formed by the addition of tert-butyl radicals to C-2 of the quinolinium cation react in Me(2)SO by proton loss followed by one-electron oxidation (1a, R = H, Me, Cl). For the N-methyl, or N-methoxyquinolinium cations proton loss is not observed and the radical cations react by one-electron reduction (1b, R = Me, Cl; Ic, R = Me), With quinoline N-oxide and its 4-substituted derivatives the C-2 adduct radicals (1d, R = H, Me, Cl) are deprotonated by DABCO to yield after one-electron oxidation the 2-tert-butylquinoline N-oxides. The adduct radical cations formed by t-Bu(.) addition at the C-4 of quinolinium ions 2 seldom lose the C-4 proton but react by reduction, hydration, or in the case of 2-chloroquinoline N-oxide, dimerization. The loss of the proton from the 2-adducts 1 but not from the 4-adducts 2 seems to be stereoelectronic in origin. With N-methylquinolinium cation the addition of t-Bu(.) occurs selectively (>90%) at C-4 in contrast to the low selectivity observed in addition to quinolinium ion itself. However, with N-methoxyquinolinium perchlorate the major reaction products (70-90%) result from the addition of t-Bu(.) at C-2.