3-(6-甲氧基-2-萘基)丙酸乙酯 | 102390-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-(6-甲氧基-2-萘基)丙酸乙酯
• 英文名称: ethyl 3-(6-methoxy-2-naphthalenyl)propanoate
• 英文别名: ethyl 3-(6-methoxy-2-naphthyl)propanoate；3-(6-methoxy-[2]naphthyl)-propionic acid ethyl ester；3-(6-Methoxy-[2]naphthyl)-propionsaeure-aethylester；Ethyl 3-(6-methoxynaphthalen-2-yl)propanoate
• CAS: 102390-49-8
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: GWYINCIFRDQTTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(6-甲氧基-2-萘基)丙酸乙酯 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(6-methoxynaphthalen-2-yl)propanoic acid
  参考文献：
  名称：

  Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid

  摘要：

  The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.080
• 作为产物：
  描述：

  6-甲氧基-2-萘甲醛 在 5%-palladium/activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 3-(6-甲氧基-2-萘基)丙酸乙酯
  参考文献：
  名称：

  Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid

  摘要：

  The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.080

文献信息

• CHLORO-PYRAZINE CARBOXAMIDE DERIVATIVES WITH EPITHELIAL SODIUM CHANNEL BLOCKING ACTIVITY
  申请人：Parion Sciences, Inc.

  公开号：US20140171447A1

  公开（公告）日：2014-06-19

  This invention provides compounds of the formula I: and their pharmaceutically acceptable salts, useful as sodium channel blockers, compositions containing the same, therapeutic methods and uses for the same and processes for preparing the same.

  这项发明提供了式I的化合物及其药用盐，可用作钠通道阻滞剂，包含这些化合物的组合物，以及用于这些化合物的治疗方法和用途，以及制备这些化合物的方法。
• Chemoselective Heck arylation of acrolein diethyl acetal catalyzed by an oxime-derived palladacycle
  作者：Carmen Nájera、Luis Botella

  DOI：10.1016/j.tet.2005.06.059

  日期：2005.10

  at 90 °C in aqueous DMA using (dicylohexyl)methylamine as base, whereas for bromoarenes the reaction has to be performed at 120 °C using tetra-n-butylammonium bromide (TBAB) as additive. Alternatively, this process can be performed under microwave irradiation. These couplings take place in good yields and with lower catalyst loading than with palladium(II) acetate as well as in shorter reaction times

  甲二聚4-羟基苯乙酮肟衍生钯化合物已被用作一种非常有效的预催化剂用于通过反应条件的适当选择丙烯醛缩二乙醇，得到任一肉桂醛衍生物或3- arylpropanoate酯的化学选择性芳基化。肉桂醛衍生物的合成可以通过丙烯醛缩二乙醇与碘，在溴-或氯代芳烃的Heck反应进行Ñ，Ñ用k二甲基乙酰胺（DMA）2 CO 3作为在120℃下和四-碱Ñ-醋酸丁丁基铵（TBAA）和氯化钾作为添加剂，然后进行酸处理。对于3-芳基丙酸酯，相应的丙烯醛二乙缩醛与碘芳烃的芳基化反应可以在90°C的DMA水溶液中使用（二（己基己基）甲胺）碱进行，而溴芳烃的反应则必须在120°C的条件下使用四芳基进行。 -溴化正丁基铵（TBAB）作为添加剂。或者，该过程可以在微波辐射下进行。与乙酸钯（II）相比，这些偶联以高收率和较低的催化剂负载量发生，并且反应时间较短且丙烯醛二乙基缩醛过量的发生率较低。
• Nickel-Catalyzed Electrochemical Arylation of Activated Olefins
  作者：Sylvie Condon、Daniel Dupré、Gilles Falgayrac、Jean-Yves Nédélec

  DOI：10.1002/1099-0690(20021)2002:1<105::aid-ejoc105>3.0.co;2-j

  日期：2002.1

  Nickel-catalyzed electrochemical conjugate additions of substituted aryl bromides to activated olefins under recently optimized reaction conditions are reported. Good to high yields were obtained, whatever the nature of substituents in the meta- and para-positions of the benzene ring. In the ortho-substituted series, yields were good with electron-donating substituents, but low with electron-withdrawing

  据报道，在最近优化的反应条件下，镍催化的取代芳基溴化物与活化烯烃的电化学共轭加成。无论苯环的间位和对位取代基的性质如何，都获得了良好到高的产率。在邻位取代系列中，给电子取代基的产率良好，但吸电子基团的产率低。还研究了芳基氯化物的活化和芳基二卤化物的顺序功能化。
• Ligand-enabled palladium-catalyzed hydroesterification of vinyl arenes with high linear selectivity to access 3-arylpropanoate esters
  作者：Zhixin Deng、Sheng Han、Miaolin Ke、Yingtang Ning、Fen-Er Chen

  DOI：10.1039/d2cc00228k

  日期：——

  Palladium-catalyzed linear-selective hydroesterification of vinyl arenes with alcohols enabled by diphosphine ligands derived from bis[2-(diphenylphosphino)ethyl]amides has been developed. A variety of 3-arylpropanoate esters were obtained in high yields and regioselectivity. The robustness of this methodology was further demonstrated by the efficient gram-scale synthesis of the ethyl 3-phenylpropanoate

  已经开发了由衍生自双[2-(二苯基膦基)乙基]酰胺的二膦配体实现的乙烯基芳烃与醇的钯催化线性选择性加氢酯化反应。以高产率和区域选择性获得了多种 3-芳基丙酸酯。3-苯基丙酸乙酯作为氢化肉桂酸前体的有效克级合成进一步证明了该方法的稳健性。
• US7871822B2
  申请人：——

  公开号：US7871822B2

  公开（公告）日：2011-01-18