β-Aethyl-α-cyan-cis-zimtsaeure-aethylester | 13434-46-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: β-Aethyl-α-cyan-cis-zimtsaeure-aethylester
• 英文别名: Ethyl 2-cyano-3-phenyl delta2-pentenoate；ethyl (Z)-2-cyano-3-phenylpent-2-enoate
• CAS: 13434-46-3
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: LYBDDDYNWSIADW-SEYXRHQNSA-N

物化性质

• 沸点：
  342.1±30.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  β-Aethyl-α-cyan-cis-zimtsaeure-aethylester 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 2-chloro-5-methyl-4-phenylnicotinic acid
  参考文献：
  名称：

  Amide-based atropisomers in tachykinin NK1-receptor antagonists: synthesis and antagonistic activity of axially chiral N-benzylcarboxamide derivatives of 2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocin-6-one

  摘要：

  A series of novel N-benzylcarboxamide derivatives of bicyclic compounds, 3,4-dihydropyrido[3,2-f][1,4]oxazepin-5(2H)-one and 2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocin-6-one, were synthesized by cyclization of N-benzyl-2-chloro-N-(2-hydroxyethyl)-and -(3-hydroxypropyl)-nicotinamides, respectively. Atropisomerism was observed in 5-[3,5-bis(trifluoromethyl)benzyl]-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocin-6-ones due to steric hindrance of the carboxamide moiety and restriction of its rotation. Cyclization of N-[3,5-bis(trifluoromethyl)benzyl]-2-chloro-N-[(2S)-3-hydroxy-2-methylpropyl]-5-methyl-4-phenylnicotinamide gave (3S)5-[3,5-bis(trifluoromethyl)benzyl]-3,8-dimethyl-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3b][1,5]oxazocin-6-one, which exists predominantly in the thermodynamically stable aR-conformer in CDCl3. This compound showed excellent NK1-antagonistic activity with IC50 value (in vitro inhibition of [I-125]-Bolton-Hunter-substance P binding in human IM-9 cells) of 0.47 nM, which is ca. 200-fold more potent than that of its enantiomer, indicating that the atropisomer chirality affects NK1-receptor recognition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.097
• 作为产物：
  描述：

  氰乙酸乙酯 、 苯丙酮 在 乙酸铵 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.2h， 生成 β-Aethyl-α-cyan-cis-zimtsaeure-aethylester
  参考文献：
  名称：

  取代的 2-氨基-3-碳乙氧基噻吩的有效合成

  摘要：

  摘要 已经开发了一种用于合成各种噻吩邻氨基酯 (2a-l) 的微波辅助方法，在元素硫的存在下，从合适的醛、甲基酮或乙酰乙酸乙酯与氰基乙酸乙酯开始。

  DOI：

  10.1080/00397910701575889

文献信息

• [EN] THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS<br/>[FR] UTILISATION DE DERIVES DE LA THIENOPYRIMIDINE COMME INHIBITEURS DES CANAUX POTASSIQUES
  申请人：XENTION DISCOVERY LTD

  公开号：WO2004111057A1

  公开（公告）日：2004-12-23

  The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.

  本发明提供了硫代嘧啶类化合物，它们是钾通道抑制剂。还提供了包含这些化合物的药物组合物，以及它们在治疗心律失常中的用途。
• The preparation of highly branched ketones and alcohols
  作者：W. A. Mosher、P. W. Berger、A. P. Foldi、J. E. Gardner、T. J. Kelly、C. Nebel

  DOI：10.1039/j39690000121

  日期：——

  A procedure is described for the preparation of highly branched ketones and alcohols with the general formulae R2R3R4C·CHR5·CO·R1 and R2R3R4C·CHR5·CR6(OH)R1. The multi-step route involves classical synthetic methods which give good yields. R may be varied and can be either alkyl or aryl.

  描述了制备通式为R 2 R 3 R 4 C·CHR 5 ·CO·R 1和R 2 R 3 R 4 C·CHR 5 ·CR 6（OH）R的高度支化的酮和醇的方法1。多步路线涉及经典的合成方法，可提供良好的收率。R可以变化并且可以是烷基或芳基。
• Facile Epoxidation of Alumina-Supported Electrophilic Alkenes and Montmorillonite-Supported Electrophilic Alkenes with Sodium Hypochlorite
  作者：André Foucaud、Médard Bakouetila

  DOI：10.1055/s-1987-28104

  日期：——

  Alkenes gem-substituted by two electron-withdrawing substituents, dispersed on alumina or montmorillonite, are conveniently epoxided by sodium hypochlorite. A mixture of aldehyde and methylcyanoacetate or malononitrile, treated with alumina and sodium hypochlorite gives the corresponding epoxide in good yield.

  被两个电子吸引基团取代的烯烃，分散在铝土矿或蒙脱石上，可以方便地用次氯酸钠进行环氧化。用铝土矿和次氯酸钠处理的醛与甲基氰乙酸酯或丙二腈的混合物，可以在良好的产率下得到相应的环氧化物。
• Compounds
  申请人：Ford John

  公开号：US20050026935A1

  公开（公告）日：2005-02-03

  This invention relates to novel compound of formula (I) or pharmaceutically acceptable salts thereof. The invention is also directed to the uses of compounds having formula (I) in the treatment or prevention of diseases or disorders which requires potassium channel inhibition to an animal, mammal or human in need thereof. The invention is also directed to the use of compounds having formula (I) in the treatment or prevention of arrhythmia to an animal, mammal or human in need thereof.

  本发明涉及公式(I)的新化合物或其药学上可接受的盐。该发明还涉及使用具有公式(I)的化合物在需要钾通道抑制的动物、哺乳动物或人类中治疗或预防疾病或障碍的用途。该发明还涉及使用具有公式(I)的化合物在需要治疗或预防心律失常的动物、哺乳动物或人类中的用途。
• Thieno[2,3-b]pyridines as Potassium Channel Inhibitors
  申请人：FORD John

  公开号：US20100041695A1

  公开（公告）日：2010-02-18

  The invention provides compounds of the formula: wherein R1 is aryl, heteroaryl, cycloalkyl or alkyl; R2 is H, alkyl, nitro, CO 2 R7, CONR5R6 or halo; R3 and R4 are H, NR5R6, NC(O)R7, halo, trifluoromethyl, alkyl, CONR5R6, CO 2 R7, nitrile or alkoxy; R5 and R6 may be the same or different and may be H, alkyl, aryl, heteroaryl or cycloalkyl; or R5 and R6 may together form a saturated, unsaturated or partially saturated 4 to 7 member ring, wherein said ring may optionally comprise one or more further heteroatoms selected from N, O or S; R7 is H or alkyl; A is H, halo, or a group of formula X-L-Y; X is O, S or NR8; R8 is H or alkyl; L is (CH 2 ) n , where n is 0, 1, 2, 3 or 4; and Y is aryl, a heterocyclic group, alkyl, alkenyl or cycloalkyl; the products of mono- and di-oxidation of sulphur and/or mono-oxidation of nitrogen moieties in compounds of formula I; or a pharmaceutically acceptable salt thereof. These compounds find use as inhibitors of potassium ion channels and thus are useful in the treatment of various conditions including arrhythmia and type-2 diabetes mellitus.

  该发明提供了以下式子的化合物：其中，R1是芳基，杂环芳基，环烷基或烷基；R2是H，烷基，硝基，CO2R7，CONR5R6或卤素；R3和R4是H，NR5R6，NC（O）R7，卤素，三氟甲基，烷基，CONR5R6，CO2R7，腈或烷氧基；R5和R6可能相同或不同，可以是H，烷基，芳基，杂环芳基或环烷基；或者R5和R6可以共同形成饱和的、不饱和的或部分饱和的4到7成员环，其中该环可以选择地包含一个或多个来自N、O或S的进一步杂原子；R7是H或烷基；A是H、卤素或公式X-L-Y的基团；X是O、S或NR8；R8是H或烷基；L是（CH2）n，其中n为0、1、2、3或4；而Y是芳基、杂环基、烷基、烯基或环烷基；该式I中硫单氧化物和/或氮单氧化物基团的单氧化和二氧化产物；或其药学上可接受的盐。这些化合物可用作钾离子通道的抑制剂，因此对于治疗包括心律不齐和2型糖尿病在内的各种疾病是有用的。

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