ethyl 5-(4-pyridyl)-pentadienoate | 1017294-36-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 5-(4-pyridyl)-pentadienoate
• 英文别名: 5-Pyridin-4-yl-penta-2,4-dienoic acid ethyl ester；ethyl 5-pyridin-4-ylpenta-2,4-dienoate
• CAS: 1017294-36-8
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: WVLZMEKZVPGCKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-pyridyl)-pentadienoate 在 palladium on activated charcoal 氯化亚砜 、 氢气 、 二异丁基氢化铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 5-(4-Pyridinyl)-pentylchloride
  参考文献：
  名称：

  Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives

  摘要：

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.

  DOI：

  10.1021/jm00142a006
• 作为产物：
  描述：

  4-(diethoxyphosphoryl)-but-2-enoic acid ethyl ester 在 lithium hexamethyldisilazane 、 4-吡啶甲醛 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以88%的产率得到ethyl 5-(4-pyridyl)-pentadienoate
  参考文献：
  名称：

  带有两亲性侧链的4-烷基吡啶的分子内环化流形：螺二氢吡啶的构建或通过无水中间体的苯甲酸环化

  摘要：

  在用氯甲酸乙酯和亚化学计量的Ti（O i Pr）4处理后，具有亲核β-二羰基侧链的4-烷基吡啶已转化为螺二氢吡啶。或者，发现在反应介质中包含温和的碱有助于促进脱水碱中间体的产生。随后与亲电子侧链部分的醛醇状缩合，然后水解，以高收率递送苄基环化的吡啶。环化脱水碱中间体的原位氢化得到4-取代的哌啶。

  DOI：

  10.1021/jo301247c

文献信息

• VEHICLE FOR THE TRANSPORT OF A CHOSEN MOLECULE TO A CELL
  申请人：Ruiters Herman Jozef Marcel

  公开号：US20080085273A1

  公开（公告）日：2008-04-10

  Vehicle for the transport of a chosen molecule to a cell, comprising a SAINT-molecule which is bound to the chosen molecule by means of an electrostatic interaction, in which the SAINT-molecule is coupled to the linker molecule and the linker molecule is coupled to the cell specific ligand and in which the SAINT-molecule is covalently bound to the linker molecule.

  一种用于将选择的分子运输到细胞的载体，包括通过静电相互作用与所选分子结合的SAINT分子，其中SAINT分子与连接分子耦合，并且连接分子与特定于细胞的配体耦合，且SAINT分子与连接分子共价结合。
• Highly selective inhibitors of thromboxane synthetase. 2. Pyridine derivatives
  作者：Tadao Tanouchi、Masamori Kawamura、Isao Ohyama、Ikuo Kajiwara、Yohichi Iguchi、Takanori Okada、Tsumoru Miyamoto、Ken Taniguchi、Masaki Hayashi

  DOI：10.1021/jm00142a006

  日期：1981.10

  The enzyme thromboxane (TX) synthetase is inhibited by pyridine. The beta-substituted pyridine derivatives showed higher inhibitory potency than the gamma-substituted ones having the same side chain. Among the beta-substituted derivatives containing the omega-carboxyalkyl group, the compounds with 6-8 carbon atoms in the side chain were especially effective. The derivatives holding the phenylene group in the side chain exhibited much higher inhibitory activity than those of the alkylene type. Among them, (E)-3-[4-(3-pyridylmethyl)phenyl]-2-methylacrylic acid hydrochloride (5a) had the highest potency (IC50 = 3 x 10(-9) M). The beta-substituted pyridine derivatives and 1-substituted imidazole derivatives which had the same side chain showed almost the same potency. The beta-substituted pyridine derivatives do not inhibit arachidonic acid cyclooxygenase or prostaglandin I2 synthetase, two other enzymes of the arachidonic cascade.
• Intramolecular Cyclization Manifolds of 4-Alkylpyridines Bearing Ambiphilic Side Chains: Construction of Spirodihydropyridines or Benzylic Cyclization via Anhydrobase Intermediates
  作者：Sharavathi G. Parameswarappa、F. Christopher Pigge

  DOI：10.1021/jo301247c

  日期：2012.9.21

  side chains have been converted to spirodihydropyridines upon treatment with ethyl chloroformate and sub-stoichiometric amounts of Ti(OiPr)4. Alternatively, inclusion of mild base in the reaction medium was found to facilitate generation of anhydrobase intermediates. Subsequent aldol-like condensations with electrophilic side chain moieties followed by hydrolysis delivered benzylically cyclized pyridines

  在用氯甲酸乙酯和亚化学计量的Ti（O i Pr）4处理后，具有亲核β-二羰基侧链的4-烷基吡啶已转化为螺二氢吡啶。或者，发现在反应介质中包含温和的碱有助于促进脱水碱中间体的产生。随后与亲电子侧链部分的醛醇状缩合，然后水解，以高收率递送苄基环化的吡啶。环化脱水碱中间体的原位氢化得到4-取代的哌啶。