P-丁基氧基苯甲醛 | 50262-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: P-丁基氧基苯甲醛
• 英文名称: 4-(n-Butyryloxy)benzaldehyd
• 英文别名: 4-ethylacetoxy benzaldehyde；4-formylphenyl butyrate；4-butyroxybenzaldehyde；Butanoic acid, 4-formylphenyl ester；(4-formylphenyl) butanoate
• CAS: 50262-49-2
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD00021058
• 分子量: 192.214
• InChiKey: DAFTVVBQFUITOL-UHFFFAOYSA-N

物化性质

• LogP：
  2.284 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 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：

  P-丁基氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到4-(hydroxymethyl)phenyl butyrate
  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：

  对羟基苯甲醛 、 丁酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到P-丁基氧基苯甲醛
  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

文献信息

• BISPHOSPHONATE COMPOUNDS
  申请人：Ebetino Frank Hallock

  公开号：US20110098251A1

  公开（公告）日：2011-04-28

  Novel bisphosphonate cyclic acetal compounds are disclosed, as well as methods of preparing the compounds, pharmaceutical compositions including the compounds, and administration of the compounds in methods of treating bone metabolism disorders, such as abnormal calcium and phosphate metabolism.

  揭示了一种新型的双膦酸环缩醛化合物，以及制备这些化合物的方法，包括这些化合物的药物组合物，以及在治疗骨代谢紊乱的方法中给予这些化合物的方法，例如异常的钙和磷代谢。
• [2+2] Photodimerization of Stilbazoles Promoted by Oxalic Acid in Suspension
  作者：Thanh Binh Nguyen、Tuan Minh Nguyen、Pascal Retailleau

  DOI：10.1002/chem.201905597

  日期：2020.4.9

  waxy or even insoluble stilbazoles. Moreover, the oxalic acid loading could be lowered to sub-stoichiometric amounts. When further optimizations were needed, our strategy was found to be highly flexible to identify other oligocarboxylic acids as alternative additive to improve or even overturn regioselectivity. Oxalic acid and other oligocarboxylic acids were found to be capable of orienting more than

  在这项研究中，我们报道了一种非常简单的技术，可以有效地对某些乙烯基吡啶进行光二聚化。通过用几种苯乙烯基唑与分散在非极性（例如环己烷）或中等极性（苯，二氯甲烷，二恶烷）溶剂中的固体草酸二水合物的搅拌混合物进行辐照，可以高收率获得相应的二聚环丁烷加合物，具有极好的区域选择性。和立体选择性。该策略也可以成功地应用于油性，蜡质或什至不溶性斯蒂巴唑。此外，草酸负载量可降低至亚化学计量量。当需要进一步优化时，我们的策略非常灵活，可以确定其他低聚羧酸作为替代添加剂，从而改善甚至推翻区域选择性。
• TEMPLATED MOLECULES AND METHODS FOR USING SUCH MOLECULES
  申请人：NUEVOLUTION A/S

  公开号：US20150315567A1

  公开（公告）日：2015-11-05

  The present invention relates to a method for synthesising templated molecules. In one aspect of the invention, the templated molecules are linked to the template which templated the synthesis thereof. The intion allows the generation of libraries which can be screened for e.g. therapeutic activity.

  本发明涉及一种合成模板分子的方法。在本发明的一个方面中，模板分子与模板连接在一起，从而模板化其合成。该方法允许生成图书馆，可用于筛选例如治疗活性。
• Preparation of amino acids from unsaturated hydantoins
  申请人：STAUFFER CHEMICAL COMPANY

  公开号：EP0177072A2

  公开（公告）日：1986-04-09

  Amino acids can be easily prepared by reducing unsaturated hydantoins to the corresponding saturated hydantoins by hydrogenating the unsaturated hydantoin using either Raney Nickel catalyst in the presence of more than a stoichiometric amount of caustic or by using zinc and hydrochloric acid followed by hydrolyzing the resultant composition with at least 3 molar equivalents of an alkali metal hydroxide to produce a racemate of an alpha amino acid. The amino acid in suitable derivative form can then be resolved particularly using a two-phase solvent system. The residual isomer of the amino acid remaining after the resolution process can then be racemized using either pyridoxal-5-phosphate or an aliphatic acid in combination with an aldehyde or a ketone. By these procedures, it is possible to obtain high yields of amino acids.

  通过使用雷尼镍催化剂在超过一定量的苛性碱存在下将不饱和海因氢化，或使用锌和盐酸将不饱和海因氢化，然后用至少 3 摩尔当量的碱金属氢氧化物水解所得到的组合物，生成α-氨基酸的外消旋体，从而将不饱和海因还原成相应的饱和海因，可以很容易地制备氨基酸。然后，以适当的衍生物形式存在的氨基酸可以通过两相溶剂系统进行溶解。然后，可使用吡哆醛-5-磷酸或脂肪族酸与醛或酮结合，对解析过程后残留的氨基酸异构体进行消旋化。通过这些程序，可以获得高产率的氨基酸。
• Promotion of raney nickel catalyst
  申请人：STAUFFER CHEMICAL COMPANY

  公开号：EP0210683A1

  公开（公告）日：1987-02-04

  There is disclosed a number of processes for the promotion of the Raney Nickel catalyzed hydrogenation of carbon-carbon double bonds. (a) One process uses tertiary amines to promote the Raney Nickel catalyzed hydrogenation. (b) Another process uses acetylene and acetylene derivatives to promote the Raney Nickel catalyzed hydrogenation. The promotion of Raney Nickel catalyst is particularly suited for the reduction of unsaturated hydantoins to saturated hydantoins and also for the reduction of cyclic and acyclic olefins and diolefins to the corresponding cyclic and acyclic alkanes.

  已公开了一些促进拉尼镍催化碳碳双键氢化的工艺。 (a) 一种工艺使用叔胺促进拉尼镍催化氢化。 (b) 另一种工艺使用乙炔和乙炔衍生物促进拉尼镍催化氢化。 拉尼镍催化剂的促进作用特别适用于将不饱和海因还原为饱和海因，也适用于将环状和非环状烯烃和二烯烃还原为相应的环状和非环状烷烃。

表征谱图