4-formylphenyl (+/-)-2'-methylbutanoate | 503584-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-formylphenyl (+/-)-2'-methylbutanoate
• 英文别名: 4-formylphenyl 2-methylbutanoate；(4-formylphenyl) 2-methylbutanoate
• CAS: 503584-36-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: NJESBQRBYJJCFS-UHFFFAOYSA-N

物化性质

• 熔点：
  79.5-80.0 °C
• 沸点：
  312.8±25.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-formylphenyl (+/-)-2'-methylbutanoate 在 sodium tetrahydroborate 、 tin(II) chloride dihdyrate 作用下， 以 四氢呋喃 、 乙腈 、 苯 为溶剂， 反应 1.0h， 生成 4-((((3-aminopyridin-4-yl)carbamoyl)oxy)methyl)phenyl 2-methylbutanoate
  参考文献：
  名称：

  Formulating a new basis for the treatment against botulinum neurotoxin intoxication: 3,4-Diaminopyridine prodrug design and characterization

  摘要：

  Botulism is a disease characterized by neuromuscular paralysis and is produced from botulinum neurotoxins (BoNTs) found within the Gram positive bacterium Clostridium botulinum. This bacteria produces the most deadliest toxin known, with lethal doses as low as 1 ng/kg. Due to the relative ease of production and transport, the use of these agents as potential bioterrorist weapons has become of utmost concern. No small molecule therapies against BoNT intoxication have been approved to date. However, 3,4-diaminopyridine (3,4-DAP), a potent reversible inhibitor of voltage-gated potassium channels, is an effective cholinergic agonist used in the treatment of neuromuscular degenerative disorders that require cholinergic enhancement. 3,4-DAP has also been shown to facilitate recovery of neuromuscular action potential post botulinum intoxication by blocking K(+) channels. Unfortunately, 3,4-DAP displays toxicity largely due to blood-brain-barrier (BBB) penetration. As a dual-action prodrug approach to cholinergic enhancement we have designed carbamate and amide conjugates of 3,4-DAP. The carbamate prodrug is intended to be a slowly reversible inhibitor of acetylcholinesterase (AChE) along the lines of the stigmines thereby allowing increased persistence of released acetylcholine within the synaptic cleft. As a secondary activity, cleavage of the carbamate prodrug by AChE will afford the localized release of 3,4-DAP, which in turn, will enhance the pre-synaptic release of additional acetylcholine. Being a competitive inhibitor with respect to acetylcholine, the activity of the prodrug will be greatest at the synaptic junctions most depleted of acetylcholine. Here we report upon the synthesis and biochemical characterization of three new classes of prodrugs intended to limit previously reported stability and toxicity issues. Of the prodrugs examined, compound 32, demonstrated the most clinically relevant half-life of 2.76 h, while selectively inhibiting AChE over butyrylcholinesterase-a plasma-based high activity esterase. Future in vivo studies could provide validation of prodrug 32 as a potential treatment against BoNT intoxication as well as other neuromuscular disorders. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.019
• 作为产物：
  描述：

  2-甲基丁酸 、 对羟基苯甲醛 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 4-formylphenyl (+/-)-2'-methylbutanoate
  参考文献：
  名称：

  手性三聚亚苯基亚乙烯基的分子构型对其液晶性能的影响

  摘要：

  根据1H NMR，FT-IR，UV-vis光谱分析，确定由Wittig反应合成的手性三聚亚苯基亚乙烯基衍生物（ChTPV）具有反式-顺式构型，并且可以异构化为反式用碘处理时，-反式异构体。与反式-顺式异构体相比，具有反式-反式构型的ChTPV的熔点提高了162.1°C，具有反式-反式构型的ChTPV在加热过程中表现出近晶A的典型液晶结构。结果表明，分子构型可以影响ChTPV液晶相的形成。

  DOI：

  10.1016/j.cclet.2013.02.013

文献信息

• Rigid-Rod β-Barrel Ion Channels with Internal “Cascade Blue” Cofactors − Catalysis of Amide, Carbonate, and Ester Hydrolysis
  作者：Abhigyan Som、Stefan Matile

  DOI：10.1002/1099-0690(200211)2002:22<3874::aid-ejoc3874>3.0.co;2-6

  日期：2002.11

  6-trisulfonate scaffold is introduced as an internal cofactor for histidine-rich p-octiphenyl s-barrels with catalytic and ion channel activity to mediate binding and conversion of otherwise inaccessible benzaldehyde substrates. Up to 170,000-fold accelerations of amide, ester, and carbonate hydrolysis, high substrate diversity, high chemoselectivity, and absence of enantioselectivity are reported.

  芘-1,3,6-三磺酸盐支架被引入作为富含组氨酸的 p-octiphenyl s-barrels 的内部辅助因子，具有催化和离子通道活性，以介导其他难以接近的苯甲醛底物的结合和转化。据报道，酰胺、酯和碳酸酯水解的速度高达 170,000 倍，底物多样性高，化学选择性高，并且没有对映选择性。