氢化奎尼定 4-甲基-2-喹啉甲醚 | 135042-89-6

• 物质功能分类: 原料药 - 循环系统用药
• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 中文名称: 氢化奎尼定 4-甲基-2-喹啉甲醚
• 中文别名: 氢奎并啶4-甲基-2-喹啉基醚；氢化奎尼定4-甲基-2-喹啉甲醚
• 英文名称: 9-O-(4'-methyl-2'-quinolyl) ether of dihydroquinidine
• 英文别名: DHQD-4-MEQ；DHQD-MEQ；(2R,4S,5R)-5-Ethyl-2-((S)-(6-methoxyquinolin-4-yl)((4-methylquinolin-2-yl)oxy)methyl)quinuclidine；2-[(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]-4-methylquinoline
• CAS: 135042-89-6
• 化学式: C₃₀H₃₃N₃O₂
• 分子量: 467.611
• InChiKey: XNLQXNDAUCSSKU-YVFWCQEHSA-N

物化性质

• 熔点：
  151-153 °C(lit.)
• 沸点：
  632.2±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 1544

制备方法与用途

概述

氢化奎尼定属于喹啉生物碱类化合物，易溶于热乙醇，微溶于水和乙醚。其盐酸盐为小片状结晶，易溶于甲醇、氯仿，微溶于水或乙醇，难溶于醋酸。它是一种抗心律失常药，作用类似于奎尼丁，并且口服毒性略低于奎尼丁。

用途

氢化奎尼定也是一种重要的医药中间体。尽管其制备方法的报道较少，但目前的方法通常产品收率较低且制备成本高。4-甲基-2-喹啉甲醚作为一种新颖的氢化奎尼定属喹琳生物碱类化合物，具有一定的研究价值和应用前景。

反应信息

• 作为产物：
  描述：

  氢化奎尼定 、 4-甲基-2-氯-喹啉 在 sodium hydride 作用下， 生成 氢化奎尼定 4-甲基-2-喹啉甲醚
  参考文献：
  名称：

  New ligands double the scope of the catalytic asymmetric dihydroxylation of olefins

  摘要：

  Improved ligands render terminal olefins good substrates for the osmium-catalyzed asymmetric dihydroxylation (ADH) process, and the amounts of chiral ligand and osmium catalyst required diminish dramatically.

  DOI：

  10.1021/jo00015a001
• 作为试剂：
  描述：

  3,3-二甲基-1-丁烯 在 potassium dioxotetrahydroxoosmate(VI) 、 potassium carbonate 、 氢化奎尼定 4-甲基-2-喹啉甲醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 生成 (R)-3,3-dimethylbutane-1,2-diol 、 (2S)-3,3-dimethylbutane-1,2-diol
  参考文献：
  名称：

  Nucleophilic Reactions between Cyclic 1,2-Sulfites and Chloride Ions.

  摘要：

  When cyclic 1,2-sulfites are ring opened by chloride ion, the chlorohydrins are formed with low regio and stereo-selectivity. The mechanisms involved in the process were investigated by measuring the stereochemical outcome of the reactions. The results showed that reversible inversion pathways (S(N)2 reactions) and a retention pathway (S(N)2i reaction) gave rise to the loss in ee in both the chlorohydrins and in the cyclic 1,2-sulfites.

  DOI：

  10.3891/acta.chem.scand.50-0832

文献信息

• Multifunctional catalyst useful in the synthesis of chiral vicinal diols and process for the preparation thereof
  申请人：Council of Scientific and Industrial Research

  公开号：EP1346767A1

  公开（公告）日：2003-09-24

  The present invention relates to a multifunctional reusable catalyst and to a process for the preparation thereof on a single matrix of the support to perform multicomponent reaction in a single pot. The multifunctional catalysts of the invention are useful for the synthesis of chiral vicinal diols by tandem and / or simultaneous reactions involving Heck coupling, N-oxidation and AD reaction of olefins in presence of cinchona alkaloid compounds both as an native one and immobilized one in the said matrix support. This invention also relates to a process for preparing vicinal diols by asymmetric dihydroxylation of olefins in presence of cinchona alkaloid compounds employing reusable multifunctional catalysts as heterogeneous catalysts in place of soluble osmium catalysts.

  本发明涉及一种多功能可重复使用的催化剂，以及一种在单一支撑基质上制备该催化剂的方法，用于在单一锅中执行多组分反应。本发明的多功能催化剂可用于在金鸡纳生物碱化合物的存在下，通过串联和/或同时反应合成手性邻二醇，涉及 Heck 偶联、N-氧化和烯烃的 AD 反应。该催化剂可以作为原生态和固定化的形式存在于所述支撑基质中。本发明还涉及一种通过在金鸡纳生物碱化合物的存在下，利用可重复使用的多功能催化剂作为异质催化剂来代替可溶性的钌催化剂，合成邻二醇的方法。
• ORGANIC COMPOUNDS
  申请人：Yokokawa Fumiaki

  公开号：US20080319018A1

  公开（公告）日：2008-12-25

  The present invention relates to a compound of the formula I wherein R1, R2, R3, R4 and R5 are as defined in the specification, for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations a compound of that class; a method of treatment comprising administering a compound of that class and a method for its manufacture.

  本发明涉及一种具有以下公式I的化合物，其中R1、R2、R3、R4和R5如规范中所定义，用于诊断和治疗温血动物，特别是用于治疗依赖肾素活性的疾病；该类化合物用于制备用于治疗依赖肾素活性疾病的药物配方；该类化合物用于治疗依赖肾素活性的疾病；该类化合物的药物配方；包括给予该类化合物的治疗方法以及其制造方法。
• Organic Compounds
  申请人：Ehara Takeru

  公开号：US20090192148A1

  公开（公告）日：2009-07-30

  The invention relates to 3,5-substituted piperidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (=disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,5-substituted piperidine compound, and/or a method of treatment comprising administering a 3,5-substituted piperidine compound, a method for the manufacture of a 3,5-substituted piperidine compound, and novel intermediates and partial steps for its synthesis. The compounds have the formula I′ wherein R1, R2, T, R3 and R4 areas defined in the specification.

  本发明涉及3,5-取代哌啶化合物，这些化合物用于诊断和治疗温血动物，特别是用于治疗依赖肾素活性的疾病（=失调）；该类化合物用于制备治疗依赖肾素活性疾病的制剂；该类化合物用于治疗依赖肾素活性的疾病；包括3,5-取代哌啶化合物的制药配方和/或包括给予3,5-取代哌啶化合物的治疗方法，以及制造3,5-取代哌啶化合物的新型中间体和部分合成步骤。该化合物的式子为I'，其中R1、R2、T、R3和R4在规范中有定义。
• Preparation of new layered double hydroxides exchanged with osmate for asymmetric dihydroxylation of olefins to vicinal diols
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：EP1209142A1

  公开（公告）日：2002-05-29

  Layered double hydroxides exchanged with osmate of the formula [MII(1-x)MIIIx(OH)2] [OsO42-]x/2.zH2O wherein MII is a divalent cation selected from the group consisting of Mg2+, Mn2+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+ and Ca2+ and MIII is a trivalent ion selected from the group consisting of Al3+, Cr3+, Mn3+, Fe3+ and Co3+, and x is the mole fraction having a value ranging from 0.2 to 0.33, and z is the number of water molecules ranging from 1 to 4, useful as a catalyst, and a process for the preparation thereof and use thereof to manufacture vicinal diols.

  与锇酸盐交换的层状双氢氧化物，其式为[MII(1-x)MIIIx(OH)2][OsO42-]x/2。zH2O 其中 MII 是选自 Mg2+、Mn2+、Fe2+、Co2+、Ni2+、Cu2+、Zn2+ 和 Ca2+ 的二价阳离子，MIII 是选自 Al3+、Cr3+、Mn3+、Fe3+ 和 Co3+ 的三价离子，x 是摩尔分数，其值范围为 0.2至0.33，z为水分子数，范围为1至4，可用作催化剂，及其制备方法和用其制造沧烷二醇的工艺。
• 3 , 5-substitued piperidine compounds as renin inhibitors
  申请人：Novartis AG

  公开号：EP2420491A1

  公开（公告）日：2012-02-22

  The invention relates to 3,5-substituted piperidine compounds, these compounds for use in the diagnostic and therapeutic treatment of a warm-blooded animal, especially for the treatment of a disease (= disorder) that depends on activity of renin; the use of a compound of that class for the preparation of a pharmaceutical formulation for the treatment of a disease that depends on activity of renin; the use of a compound of that class in the treatment of a disease that depends on activity of renin; pharmaceutical formulations comprising a 3,5-substituted piperidine compound, and/or a method of treatment comprising administering a 3,5-substituted piperidine compound, a method for the manufacture of a 3, 5-substituted piperidine compound, and novel intermediates and partial steps for its synthesis. The compounds (which can also be present as salts) have the formula I' wherein R1, R2, T, R3, R4, R7 and R8 are as defined in the specification and R6 is OH.

  本发明涉及3,5-取代的哌啶化合物，这些化合物用于温血动物的诊断和治疗，特别是用于治疗依赖于肾素活性的疾病（=紊乱）；使用该类化合物制备药物制剂，用于治疗依赖于肾素活性的疾病；该类化合物在治疗依赖于肾素活性的疾病中的用途；包含 3,5-取代的哌啶化合物的药物制剂，和/或包括施用 3,5-取代的哌啶化合物的治疗方法，3,5-取代的哌啶化合物的制造方法，及其合成的新型中间体和部分步骤。 这些化合物（也可以以盐的形式存在）具有式 I' 其中 R1、R2、T、R3、R4、R7 和 R8 如说明书中所定义，R6 为 OH。