乙基3-(2-甲氧基苯基)丙酸酯 | 70311-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 乙基3-(2-甲氧基苯基)丙酸酯
• 英文名称: ethyl 3-(2-methoxyphenyl)propanoate
• 英文别名: 2-methoxybenzenepropanoic acid ethyl ester
• CAS: 70311-27-2
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD07772958
• 分子量: 208.257
• InChiKey: NSYRTEICIYAZDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 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：

  乙基3-(2-甲氧基苯基)丙酸酯 在 氢氧化钾 、 三氯化铝 、 硫酸 、 吡啶盐酸盐 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 106.5h， 生成 LY223982
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 2. Structure-activity relationships of the lipophilic side chain

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives were found to inhibit the binding of the potent chemotaxin leukotriene B4 (LTB4) to its receptor on intact human neutrophils. Activity at the LTB4 receptor was determined by using a [3H]LTB4-binding assay. The structure-activity relationship for the lipophilic side chain was systematically investigated. Compounds with n-alkyl side chains of varying lengths were prepared and tested. Best inhibition of [3H]LTB4 binding was observed with the n-decyl derivative. Analogues with alkyl chains terminated with an aromatic ring showed improved activity. The 6-phenylhexyl side chain was optimal. Substitution on the terminal aromatic ring was also evaluated. Methoxyl, methylsulfinyl, and methyl substituents greatly enhanced the activity of the compound. For a given substituent, the para isomer had the best activity. Thus the nature of the lipophilic side chain can greatly influence the ability of the compounds to inhibit the binding of LTB4 to its receptor on intact human neutrophils. The most active compound from this series, 84 (LY223982), bound to the LTB4 receptor with an affinity approaching that of the agonist.

  DOI：

  10.1021/jm00172a020
• 作为产物：
  描述：

  2-甲氧基肉桂酸 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 乙基3-(2-甲氧基苯基)丙酸酯
  参考文献：
  名称：

  Inhibition of uridine phosphorylase: synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils.

  摘要：

  A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine-induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 mu M), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3-alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC(50)s of 0.047 and 0.027 mu M, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 mu M.

  DOI：

  10.1021/jm00019a015

文献信息

• Discovery of Synthetic Methoxy-substituted 4-Phenylbutyric Acid Derivatives as Chemical Chaperones
  作者：Seisuke Mimori、Yasunobu Okuma、Masayuki Kaneko、Koichi Kawada、Yasuyuki Nomura、Yasuoki Murakami、Hiroshi Hamana

  DOI：10.1246/cl.130419

  日期：2013.9.5

  In this study, we evaluated the chemical chaperone activity of synthetic 4-phenylbutyric acid (4-PBA) derivatives. These derivatives have a methoxy group at the benzene ring and/or longer or shorter fatty acid portions. Several 4-PBA derivatives demonstrated higher antiaggregation activity than 4-PBA. Moreover, 4-(4-methoxyphenyl)butanoic acid (7b) showed protective effects against endoplasmic reticulum stress-induced neuronal cell death.

  本研究中，我们评估了合成4-苯基丁酸（4-PBA）衍生物的化学伴侣活性。这些衍生物在苯环上具有甲氧基和/或更长或更短的脂肪酸部分。多个4-PBA衍生物表现出比4-PBA更高的抗聚集活性。此外，4-（4-甲氧基苯基）丁酸（7b）显示出对内质网应激诱导的神经细胞死亡的保护作用。
• Nucleophilic Amination of Methoxy Arenes Promoted by a Sodium Hydride/Iodide Composite
  作者：Atsushi Kaga、Hirohito Hayashi、Hiroyuki Hakamata、Miku Oi、Masanobu Uchiyama、Ryo Takita、Shunsuke Chiba

  DOI：10.1002/anie.201705916

  日期：2017.9.18

  Come full circle: A method for the nucleophilic amination of methoxy arenes was established by using sodium hydride (NaH) in the presence of lithium iodide (LiI). This method offers an efficient route to benzannulated nitrogen heterocycles. Mechanistic studies showed that the reaction proceeds through an unusual concerted nucleophilic aromatic substitution.

  围成一圈：在碘化锂（LiI）存在下，使用氢化钠（NaH）建立了甲氧基芳烃的亲核胺化方法。该方法提供了一条有效的途径来制得二环氮杂环。机理研究表明，该反应通过异常的协同的亲核芳族取代进行。
• CoBr₂(Bpy):  An Efficient Catalyst for the Direct Conjugate Addition of Aryl Halides or Triflates onto Activated Olefins
  作者：Muriel Amatore、Corinne Gosmini、Jacques Périchon

  DOI：10.1021/jo060855f

  日期：2006.8.1

  method devoted to the direct conjugate addition of functionalized aryl compounds onto Michael acceptors is described. The CoBr2(2,2‘-bipyridine) complex appears to be an extremely suitable catalyst for the activation of a variety of aromatic reagents ranging from halides to triflates functionalized by reactive groups. This procedure allows for the synthesis of compounds resulting from 1,4-addition in good

  描述了致力于将官能化的芳基化合物直接共轭加成到迈克尔受体上的有效的钴催化方法。CoBr 2（2,2'-联吡啶）配合物似乎是一种非常合适的催化剂，可用于活化各种芳族试剂，从卤化物到被反应基团官能化的三氟甲磺酸酯。该方法允许以良好的至优异的产率合成由1，4-加成产生的化合物。该原始方法的多功能性代表了使用有机金属试剂的大多数已知方法的简单替代方案。
• [EN] 1-HETEROCYCLYL-1,5-DIHYDRO-PYRAZOLO[3,4-D] PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS PDE9A MODULATORS<br/>[FR] DÉRIVÉS DE 1-HÉTÉROCYCLYL-1,5-DIHYDRO-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE ET LEURS UTILISATIONS À TITRE DE MODULATEURS DE PDE9A
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009121919A1

  公开（公告）日：2009-10-08

  The invention relates to novel 1,6-disubstituted pyrazolopyrimidinones, Formula (I) with Hc is a mono-, bi- or tricyclic heterocyclyl group, the ring members of which are carbon atoms and at least 1, preferably 1, 2 or 3, heteroatom(s), which are selected from the group of nitrogen, oxygen and sulphur, which is in the form of -S(O)r - with r being 0, 1 or 2, and - said heterocyclyl group is or comprises 1 non-aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member and - said heterocyclyl group is bound to the scaffold by said 1 non- aromatic, saturated, or partly unsaturated monocyclic ring which comprises at least 1 heteroatom as ring member. According to one aspect of the invention the new compounds are for the manufacture of medicaments, in particular medicaments for the treatment of conditions concerning deficits in perception, concentration, learning or memory. The new compounds are also for the manufacture of medicaments for the treatment of Alzheimer's disease.

  该发明涉及新型1,6-二取代吡唑吡嘧啶酮，化学式（I），其中Hc是一个单环、双环或三环杂环基团，其环成员为碳原子和至少1个，优选1个、2个或3个来自氮、氧和硫的杂原子，其以-S(O)r-的形式存在，其中r为0、1或2，所述杂环基团是或包括1个非芳香、饱和或部分不饱和的单环环，其中至少包含1个杂原子作为环成员，所述杂环基团通过所述至少包含1个杂原子作为环成员的非芳香、饱和或部分不饱和的单环环与支架相结合。根据该发明的一个方面，新化合物用于制造药物，特别是用于治疗感知、注意力、学习或记忆缺陷相关疾病的药物。新化合物还用于制造治疗阿尔茨海默病的药物。
• Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; unexpected reductions and vinylogations
  作者：Attimogae Shivamurthy Harisha、Suresh Parameshwar Nayak、Kuppuswamy Nagarajan、Tayur Narasingarow Guru Row、Amar A. Hosamani

  DOI：10.1016/j.tet.2016.03.097

  日期：2016.6

  Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined

  在热乙醇中将2-氰基-3-（2-甲氧基-5-硝基苯基）丙烯酸乙酯1f暴露于三乙胺导致高产率地形成二氢衍生物2f和乙烯基化合物3f。提供了用于3f的单晶X射线数据。对于各种类似物观察到相似的反应。研究了改变芳基取代基，胺和溶剂的反应。还检查了吡啶基，噻吩基类似物。该研究扩展到包含这种系统，如噻唑烷二酮的环状分子8，3-氰基香豆素9和4-亚芳基-异喹啉-2,4-二酮11。最后一组给出了乙烯基化产物，4-肉桂基-异喹啉二酮和4-羟基化的物质。研究了来自丙二腈，乙酰乙酸乙酯，乙酰丙酮和甲基磺酰乙酸乙酯的亚芳基衍生物的一些实例。肉桂酸乙酯和β-硝基苯乙烯不受影响。由于添加自由基淬灭剂抑制了反应，因此认为该反应可能是自由基介导的。与热条件的影响相反，在254和365 nm的乙醇中1f的辐照产生复杂的混合物。在这项研究中还注意到了一些其他有趣的观察结果：1f与乙醛的乙烯基化反应生成3f；从1f形成3f用