2-[(3R)-3-[3-[(1E)-2-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯甲酸甲酯 | 150026-72-5

• 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
• 中文名称: 2-[(3R)-3-[3-[(1E)-2-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯甲酸甲酯
• 中文别名: 孟鲁司特(3R)羟基苯甲酸酯
• 英文名称: -2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>benzoic acid methyl ester
• 英文别名: (R,E)-methyl 2-<3-<3-<2-(7-chloro-2-quinolyl)ethenyl>phenyl>-3-hydroxypropyl>benzoate；2-(3(R)-{3-[2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-hydroxy-propyl)-benzoic acid methyl ester；(R)-2-(3-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-hydroxy-propyl)-benzoic acid methyl ester；methyl (R)-2-[3-[(E)-3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl]-3-hydroxypropyl]benzoate；methyl [R-(E)]-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoate；Methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl) ethenyl)phenyl)-3(R)-3-hydroxypropyl)benzoate；2-[3-(R)-[3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl]-3-hydroxypropyl]benzoic Acid Methyl Ester；methyl 2-[(3R)-3-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-hydroxypropyl]benzoate
• CAS: 150026-72-5
• 化学式: C₂₈H₂₄ClNO₃
• mdl: MFCD09835558
• 分子量: 457.956
• InChiKey: KPCSDMZEMDMWKQ-WKMZLRSWSA-N

物化性质

• 沸点：
  644.0±55.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(3R)-3-[3-[(1E)-2-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯甲酸甲酯 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 孟鲁司特
  参考文献：
  名称：

  New and Improved Synthesis of Montelukast, an Anti‐asthmatic Drug

  摘要：

  DOI：

  10.1080/00397910601055032
• 作为产物：
  描述：

  (E)-3-[2-(7-氯-2-喹啉基)乙烯基]苯甲醛 在 palladium diacetate chloroborane-methyl sulfide 、 乙烯基溴化镁 、 2-蒎烯聚合物 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 17.5h， 生成 2-[(3R)-3-[3-[(1E)-2-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯甲酸甲酯
  参考文献：
  名称：

  An efficient synthesis of LTD4 antagonist L-699,392

  摘要：

  The asymmetric synthesis of L-699,392 (1) [3-[[(1S)-[3(E)-[2-(7-chloroquinolinyl)ethenyl]phenyl]-3-(acetylphenyl)propyl]thiol-2(S)-methylpropanoic acid], a leukotriene antagonist, is accomplished in six steps starting from the monoaldehyde 2. The main framework of the molecule is formed via a Pd-catalyzed Heck reaction. The asymmetric center is introduced via the chiral reduction of the ketone 4 using optically active B-chlorodiisopinocampheylborane (10) derived directly from chloroborane and (-)-alpha-pinene. A very high asymmetric amplification is observed in which 95 % ee product can be obtained from 70% optically pure a-pinene. Reagent 17, which is prepared in situ from methylmagnesium chloride and 2 equiv of lithium hexamethyldisilazide, is used to convert the methyl ester 5 to the methyl ketone 6 in one step with essentially no impurities formed under the reaction conditions. The thio side chain is finally incorporated by the displacement of the chiral mesylate 7 with complete inversion at the chiral center. The overall yield for the sequence is 42%.

  DOI：

  10.1021/jo00066a027

文献信息

• Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05270324A1

  公开（公告）日：1993-12-14

  Compounds having the formula I: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.

  具有以下化学式的化合物 I: ##STR1## 是白三烯拮抗剂，也是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎症和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥反应。
• Unsaturated hydroxyalkylquinoline acids as leukotriene antagonists
  申请人：Merck Frosst Canada, Inc.

  公开号：US05565473A1

  公开（公告）日：1996-10-15

  Compounds having the formula I: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.

  具有以下化学式I的化合物是白三烯拮抗剂和白三烯生物合成抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、葡萄膜炎和移植排斥反应。
• [EN] BIARYL DIPHOSPHINE LIGANDS, INTERMEDIATES OF THE SAME AND THEIR USE IN ASYMMETRIC CATALYSIS<br/>[FR] LIGANDS BIARYLES DIPHOSPHINES, INTERMÉDIAIRES ET UTILISATION DANS LA CATALYSE ASYMÉTRIQUE
  申请人：KANATA CHEMICAL TECHNOLOGIES INC

  公开号：WO2012031358A1

  公开（公告）日：2012-03-15

  The present disclosure relates to biaryl diphosphine ligands of the formula (B), processes for the production of the ligands and the use of the ligands in metal catalysts for asymmetric synthesis. The disclosure also relates to intermediates used for the production of the biaryl diphosphine ligand. (Formula (B))

  本公开涉及公式（B）的联苯二膦配体，制备该配体的方法以及在金属催化剂中用于不对称合成的配体的使用。该公开还涉及用于生产联苯二膦配体的中间体。（公式（B））
• Process for the preparation of optically active ethenylphenyl-alcohols
  申请人：Lonza AG

  公开号：EP1988079A1

  公开（公告）日：2008-11-05

  Optically active ethenylphenyl-alcohols of formula or its mirror image, wherein R1 is unsubstituted or substituted heteroaryl and R2 is phenyl or substituted aryl, are prepared by asymmetric hydrogenation of the corresponding ketones applying hydrogen gas in the presence of specific platinum metal complex catalysts.

  利用特定的铂金属复合催化剂，在氢气存在下，通过对应酮的不对称加氢制备具有旋光性的乙烯基苯醇，其化学式为或其镜像，其中R1为未取代或取代的杂芳基，R2为苯基或取代芳基。
• Process for preparation of montelukast and its salts
  申请人：Reguri Reddy Buchi

  公开号：US20050107612A1

  公开（公告）日：2005-05-19

  A process for preparation of montelukast or a salt thereof is provided, the process including reacting a late intermediate compound which is 2-[1-[1-R-3-[2-(7 chloro quinolin-2-yl) vinyl [phenyl]-3-[2-methoxy carbonyl phenyl] propyl sulfonyl methyl] cyclo propyl] acetic acid or a salt thereof with methyl magnesium chloride or methyl magnesium bromide in an organic solvent. In one embodiment, the process includes reacting an earlier intermediate compound which is methyl 2-(3-R-(3-(2-(7-chloro 2-quinolinyl)-ethenyl)-3 hydroxy propyl) benzoate with methane sulfonyl chloride or toluene sulfonyl chloride to obtain a mesylated or tosylated derivative of the earlier intermediate compound; followed by a reaction of the mesylated or tosylated derivative with 1-mercapto methyl cyclopropane acetic acid in a polar solvent in a presence of a base to obtain the late intermediate compound.

  提供一种用于制备蒙特鲁卡斯特或其盐的过程，该过程包括在有机溶剂中将2-[1-[1-R-3-[2-(7氯喹啉-2-基)乙烯[苯基]-3-[2-甲氧羰基苯基]丙磺酰甲基]环丙基]醋酸或其盐与甲基镁氯化物或溴化物反应。在一个实施例中，该过程包括将较早的中间体化合物（甲基2-(3-R-(3-(2-(7-氯喹啉基)-乙烯基)-3-羟基丙基)苯甲酸酯）与甲磺酰氯或甲苯磺酰氯反应，以获得较早中间体化合物的甲磺酰化或甲苯磺酰化衍生物；然后将甲磺酰化或甲苯磺酰化衍生物与1-巯基甲基环丙基乙酸在极性溶剂中在碱的存在下反应，以获得晚期中间体化合物。