2-(2-((E)-3-(3-((E)-2-(7-Chloroquinolin-2-yl)vinyl)phenyl)allyl)phenyl)propan-2-ol | 168214-68-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(2-((E)-3-(3-((E)-2-(7-Chloroquinolin-2-yl)vinyl)phenyl)allyl)phenyl)propan-2-ol
• 英文别名: 2-[2-[(E)-3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]prop-2-enyl]phenyl]propan-2-ol
• CAS: 168214-68-4
• 化学式: C₂₉H₂₆ClNO
• 分子量: 439.985
• InChiKey: DLLVZUPJFUZKDX-VXFWDVHGSA-N

物化性质

• 沸点：
  611.8±43.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[2-[(3S)-3-[3-[(E)-2-(7-氯-2-喹啉基)乙烯基]苯基]-3-[(甲烷磺酰基)氧基]丙基]苯基]-2-丙醇 在 chromatography under protic conditions 作用下， 生成 2-(2-((E)-3-(3-((E)-2-(7-Chloroquinolin-2-yl)vinyl)phenyl)allyl)phenyl)propan-2-ol 、 1,1-二甲基-2-苯并革-3-基)苯基]乙烯]-
  参考文献：
  名称：

  Kinetic Analysis and Subambient Temperature Chromatography of an Active Ester

  摘要：

  The inherent instability of active esters provides a chromatographic challenge. A normal phase HPLC gradient was developed using nonprotic solvents and a diol stationary phase to determine the impurity profile of a mesylate which, under protic conditions, undergoes intramolecular ring closure to a cyclic ether. On-column cyclization of the analyte was found to be extensive at room temperature but insignificant at -30 degrees C. The on-column reaction rate was determined as a function of column temperature, and an Arrhenius activation energy was calculated.

  DOI：

  10.1021/ac00109a059

文献信息

• METHOD FOR ISOLATION AND PURIFICATION OF MONTELUKAST
  申请人：Halama Ales

  公开号：US20100267958A1

  公开（公告）日：2010-10-21

  A method of isolation of Montelukast of formula I from reaction mixtures, comprising conversion of the crude sub-stance to well-crystallizing salts with primary amines in the environment of at least one organic solvent and acetonitrile, followed by re-crystallization of these salts with simultaneous removal of chemical impurities and use of the chemically pure salts of Montelukast with primary amines for direct transformation to the pharmaceutically useful amorphous form of Montelukast sodium of formula II.

  一种从反应混合物中分离Montelukast I式化合物的方法，包括将粗品转化为与初级胺形成良好结晶的盐，其中环境包括至少一种有机溶剂和乙腈，随后再结晶这些盐，并同时去除化学杂质，使用与初级胺形成的化学纯的Montelukast盐直接转化为Montelukast II式钠的药用非晶态形式。
• METHOD FOR THE PREPARATION OF MONTELUKAST
  申请人：Halama Ales

  公开号：US20100174083A1

  公开（公告）日：2010-07-08

  A method of preparation of Montelukast of formula (I) by reaction of the compound of formula (III) and a compound of formula (IX), characterized in that the reaction is carried out in the presence of a base, an inert solvent and a component increasing selectivity of the process, especially of a polyether of general formula (XIII), wherein R stands for hydrogen or an alkyl and the value of n varies from 1 to 40, polyethyleneglycol of general formula (XIV), wherein n=1 to 40 or a crown-ether of formulae (XV), (XVI) or (XVII).

  根据公式（I）的蒙特卢卡斯特制备方法，通过化合物公式（III）和化合物公式（IX）的反应制备，其特征在于在碱、惰性溶剂和增加过程选择性的组分（特别是一般公式（XIII）的聚醚）的存在下进行反应，其中R代表氢或烷基，n值在1到40之间变化，一般公式（XIV）的聚乙二醇，其中n=1到40，或公式（XV）、（XVI）或（XVII）的冠醚。
• SPECIFIC IMPURITIES OF MONTELUKAST
  申请人：Halama Ales

  公开号：US20110034692A1

  公开（公告）日：2011-02-10

  The subject-matter of the invention consists in a method of removing specific impurities of montelukast of formula (I), which occur due to chemical instability of the target substance and also contaminate the substance in the preparation process. Further, methods of isolation of specific impurities of montelukast defined by formulae (V-A), (IV-A), (XIIIa-A), (XIIIb-A) and analytic methods used for the control of the production of montelukast in the pharmaceutical quality.

  本发明的主题是一种去除蒙特卢卡斯特（化学式（I））的特定杂质的方法，这些杂质由于目标物质的化学不稳定性而产生，并在制备过程中污染物质。此外，本发明还涉及一些隔离蒙特卢卡斯特的特定杂质的方法，这些杂质由式（V-A）、（IV-A）、（XIIIa-A）、（XIIIb-A）定义，并用于控制制药质量中蒙特卢卡斯特生产的分析方法。
• Improved Process for the Preparation of Montelukast: Development of an Efficient Synthesis, Identification of Critical Impurities and Degradants
  作者：Aleš Halama、Josef Jirman、Olga Boušková、Petr Gibala、Kamal Jarrah

  DOI：10.1021/op900311z

  日期：2010.3.19

  An improved and scalable process For the production of montelukast (Singulair, drug tor asthma) based on a new and advantageous method of carrying out the key substitution reaction has been developed. The present procedure is distinguished from file previous solutions in the use of linear or cyclic polyethers, which ensures higher selectivity of the key step. The improved process for the preparation of montelukast is able to minimize a content of impurities and allows the effective production of montelukast and its scale-tip.
• [EN] A METHOD FOR THE PREPARATION OF MONTELUKAST<br/>[FR] PROCÉDÉ DE FABRICATION DE MONTÉLUKAST
  申请人：ZENTIVA AS

  公开号：WO2008083635A1

  公开（公告）日：2008-07-17

  [EN] A method of preparation of Montelukast of formula (I) by reaction of the compound of formula (III) and a compound of formula (IX), characterized in that the reaction is carried out in the presence of a base, an inert solvent and a component increasing selectivity of the process, especially of a polyether of general formula (XIII), wherein R stands for hydrogen or an alkyl and the value of n varies from 1 to 40, polyethyleneglycol of general formula (XIV), wherein n=l to 40 or a crown-ether of formulae (XV), (XVI) or (XVII).
  [FR] L'invention porte sur un procédé de fabrication de Montélukast de formule (I) par réaction du composé de formule (III) et d'un composé de formule (IX). Ce procédé est caractérisé par le fait que la réaction est effectuée en présence d'une base, d'un solvant inerte et d'un composant augmentant la sélectivité du procédé, notamment d'un polyéther de formule générale (XIII), dans laquelle R représente hydrogène ou un alkyle, et la valeur n varie de 1 à 40, le polyéthylène glycol de formule générale (XIV), dans laquelle n=1 à 40 ou un éther-couronne de formule (XV), (XVI) ou (XVII).