(E/Z) ethyl 3-(2-methoxy-1-naphthyl)acrylate | 858438-29-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E/Z) ethyl 3-(2-methoxy-1-naphthyl)acrylate
• 英文别名: ethyl 3-(2'-methoxy-1'-naphthyl)-2-propenoate；Ethyl 3-(2-methoxynaphthalen-1-yl)prop-2-enoate
• CAS: 858438-29-6
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: JBHHZRCLRMVEKY-UHFFFAOYSA-N

物化性质

• 沸点：
  210-212 °C(Press: 4 Torr)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (E/Z) ethyl 3-(2-methoxy-1-naphthyl)acrylate 在 5%-palladium/activated carbon 、 水 、 氢气 、 sodium hydroxide 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 3-(2-甲氧基-1-萘基)丙酸
  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：

  2-甲氧基-1-萘甲醇 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E/Z) ethyl 3-(2-methoxy-1-naphthyl)acrylate
  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

• 2,5-Disubstituted tetrahydrofurans as selective serotonin re-uptake inhibitors
  作者：Troy Voelker、Haiji Xia、Keith Fandrick、Robert Johnson、Aaron Janowsky、John R. Cashman

  DOI：10.1016/j.bmc.2009.01.023

  日期：2009.3

  were prepared based on (−)-cocaine and aryltropanes as lead compounds because they are reasonably potent 5-HT re-uptake inhibitors. Molecular dissection of an aryltropane provided a series of 5- and 6-membered ring compounds. From among this library of compounds a series of disubstituted tetrahydrofurans bearing 2-alkyl aryl and 5-alkyl amino groups were identified as having highly potent and selective

  5-羟色胺（5-HT，5-羟色胺）神经传递的增强是治疗抑郁症的可行方法。基于该观察结果，基于（-）-可卡因和芳基环烷类作为先导化合物，制备了抑制5-HT再摄取的药物，因为它们是有效的5-HT再摄取抑制剂。芳基托烷的分子分解提供了一系列的5元和6元环化合物。从该化合物库中，鉴定出一系列带有2-烷基芳基和5-烷基氨基的二取代四氢呋喃具有高度有效和选择性的5-HT再摄取抑制作用。评价化合物与放射性标记的RTI-55结合竞争的能力以及在人多巴胺，5-羟色胺和去甲肾上腺素转运蛋白上抑制神经递质再摄取的能力。基于效力（例如，K i  = 800 pM）和显着的功能选择性（例如，人多巴胺：5-羟色胺或去甲肾上腺素：5-羟色胺的IC 50比，⩾1397）被确定为高效和选择性的5-羟色胺再摄取抑制剂。在结合亲和力和再摄取抑制中起主要作用的最佳特征包括芳族部分上的亲脂取代，反式2,5-二取代的四氢呋喃环的相对
• Photoinduced Single‐Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane
  作者：Peng‐Ju Xia、Dan Song、Zhi‐Peng Ye、Yuan‐Zhuo Hu、Jun‐An Xiao、Hao‐Yue Xiang、Xiao‐Qing Chen、Hua Yang

  DOI：10.1002/anie.201913398

  日期：2020.4.20

  process enables the direct B-H bond activation of NHC-boranes. In contrast to common hydrogen atom transfer (HAT) strategies, this photoinduced reaction simply takes advantage of the beneficial redox potentials of NHC-boranes, thus obviating the need for extra radical initiators. The resulting NHC-boryl radical was used for the borylation of a wide range of α-trifluoromethylalkenes and alkenes with diverse

  光诱导的SET过程使NHC-硼烷的直接BH键活化。与常见的氢原子转移（HAT）策略相比，这种光诱导反应仅利用了NHC-硼烷的有益氧化还原电位，因此无需额外的自由基引发剂。所得的NHC-硼基自由基用于使各种具有不同电子和结构特征的各种α-三氟甲基烯烃和烯烃进行硼酸酯化，从而可轻松获得高度官能化的硼酸酯化分子。标记和光猝灭实验提供了对该光诱导SET途径的机制的了解。
• Synthesis of 4-methoxy-1H-phenalen-1-one: a subunit related to natural phenalenone-type compounds
  作者：Juliana Nanclares、Jesús Gil、Benjamı´n Rojano、Jairo Saez、Bernd Schneider、Felipe Otálvaro

  DOI：10.1016/j.tetlet.2008.04.095

  日期：2008.6

  4-Methoxy-1H-phenalen-1-one (4-methoxyperinaphthenone, 1), a subunit found in some Musa phytoalexins; and related natural products from the Haemodoraceae, was synthesized starting from 2-methoxynaphthalene in five steps and an overall yield of 36%. A Heck-Fujiwara coupling between ethyl acrylate and 1-bromonaphthalene afforded the corresponding (E)-naphthylpropanoic acid which, after hydrogenolysis, was subjected to a one-pot Friedel-Crafts acylation-DDQ dehydrogenation procedure to furnish 1. (c) 2008 Elsevier Ltd. All rights reserved.