4-(3-cyanopropyl)benzoic acid | 15473-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3-cyanopropyl)benzoic acid
• 英文别名: p-Cyan-propyl-benzoesaeure
• CAS: 15473-89-9
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: VBKOLIZQULKKQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3-cyanopropyl)benzoic acid 、 1-十四烷基哌嗪 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-[4-(4-tetradecylpiperazine-1-carbonyl)phenyl]butanenitrile
  参考文献：
  名称：

  Design of new potent and selective secretory phospholipase A2 inhibitors. Part 5: Synthesis and biological activity of 1-alkyl-4-[4,5-dihydro-1,2,4-[4H]-oxadiazol-5-one-3-ylmethylbenz-4′-yl(oyl)] piperazines

  摘要：

  Among the different PLA(2)s identified to date, the group IIA secretory PLA(2) (sPLA(2) GIIA) is implied in diverse pathological conditions. In this work we describe the synthesis, inhibitory activities, and structure-activity relationships (SAR) of a new class of substituted piperazine derivatives. The in vitro fluorimetric assay using two groups of enzymes, GIB and GIIA, revealed several compounds as highly potent inhibitors (IC50 = 0.1 mu M). The in vivo activity assessed by ip or per os administration in a carrageenan-induced edema test in rats showed that two compounds proved to be as potent as indomethacin (10 mg/kg). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.077
• 作为产物：
  描述：

  4-(3-cyanopropyl)cyclohexa-1,5-diene-1,4-dicarboxylic acid 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到4-(3-cyanopropyl)benzoic acid
  参考文献：
  名称：

  芳族二羧酸两步取代反应区域选择性合成烷基芳烃

  摘要：

  开发了一种用于芳烃区域选择性烷基化的策略，从市售且廉价的对苯二甲酸或萘-1,4-二羧酸开始。该方法需要通过一系列在 Birch 条件下的还原性烷基化和随后的酸介导的重构化，在失去一氧化碳和二氧化碳的情况下对羧酸根进行正式的同位取代。合成了 20 多种不同侧链的芳烃。以萘-1,4-二羧酸为原料，我们能够通过在 Birch 还原中选择合适的亲电子试剂来控制烷基化程度。因此，双烷基化萘和萘甲酸可通过化学选择性获得。所有反应均以高产率专门提供单一区域异构体。全面的，

  DOI：

  10.1002/ejoc.201200823

文献信息

• Novel inhibitor compounds specific of secreted non-pancreatic human a<sb>2</sb>phospholipase of group II
  申请人：Heymans Francoise

  公开号：US20050075345A1

  公开（公告）日：2005-04-07

  The present invention relates to a compound of the following formula (I) and pharmaceutical compositions containing the compound of formula (I): wherein D, Y, A, B, p, q, W and R have the same meanings as defined in the specification.

  本发明涉及以下式（I）的化合物以及含有该化合物的药物组合物：其中D、Y、A、B、p、q、W和R的含义与规范中定义的含义相同。
• Design of new potent and selective secretory phospholipase A2 inhibitors. Part 5: Synthesis and biological activity of 1-alkyl-4-[4,5-dihydro-1,2,4-[4H]-oxadiazol-5-one-3-ylmethylbenz-4′-yl(oyl)] piperazines
  作者：Latifa Boukli、Mohamed Touaibia、Nadia Meddad-Belhabich、Atimé Djimdé、Chang-Ha Park、Jung-Joo Kim、Joo-Hyoung Yoon、Aazdine Lamouri、Françoise Heymans

  DOI：10.1016/j.bmc.2007.10.077

  日期：2008.2.1

  Among the different PLA(2)s identified to date, the group IIA secretory PLA(2) (sPLA(2) GIIA) is implied in diverse pathological conditions. In this work we describe the synthesis, inhibitory activities, and structure-activity relationships (SAR) of a new class of substituted piperazine derivatives. The in vitro fluorimetric assay using two groups of enzymes, GIB and GIIA, revealed several compounds as highly potent inhibitors (IC50 = 0.1 mu M). The in vivo activity assessed by ip or per os administration in a carrageenan-induced edema test in rats showed that two compounds proved to be as potent as indomethacin (10 mg/kg). (c) 2007 Elsevier Ltd. All rights reserved.
• Regioselective Synthesis of Alkylarenes by Two-Step<i>ipso</i>-Substitution of Aromatic Dicarboxylic Acids
  作者：Andrea Bramborg、Torsten Linker

  DOI：10.1002/ejoc.201200823

  日期：2012.10

  A strategy for the regioselective alkylation of arenes was developed, starting from commercially available and inexpensive terephthalic acid or naphthalene-1,4-dicarboxylic acid. The method entails a formal ipso-substitution of the carboxylate groups by a sequence of reductive alkylation under Birch conditions and subsequent acid-mediated rearomatization with loss of carbon monoxide and carbon dioxide

  开发了一种用于芳烃区域选择性烷基化的策略，从市售且廉价的对苯二甲酸或萘-1,4-二羧酸开始。该方法需要通过一系列在 Birch 条件下的还原性烷基化和随后的酸介导的重构化，在失去一氧化碳和二氧化碳的情况下对羧酸根进行正式的同位取代。合成了 20 多种不同侧链的芳烃。以萘-1,4-二羧酸为原料，我们能够通过在 Birch 还原中选择合适的亲电子试剂来控制烷基化程度。因此，双烷基化萘和萘甲酸可通过化学选择性获得。所有反应均以高产率专门提供单一区域异构体。全面的，