2-(2-ethylphenyl)acetic acid | 19418-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-ethylphenyl)acetic acid
• 英文别名: o-Ethylphenylessigsaeure
• CAS: 19418-95-2
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD09924863
• 分子量: 164.204
• InChiKey: IDWCPOOBGCOZAY-UHFFFAOYSA-N

物化性质

• 熔点：
  42 °C
• 沸点：
  270-271 °C
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-ethylphenyl)acetic acid 在 lithium aluminium tetrahydride 、 正丁基锂 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-2-(2-ethyl-phenyl)-propanol
  参考文献：
  名称：

  Potent Kv1.3 inhibitors from correolide—modification of the C18 position

  摘要：

  Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.058
• 作为产物：
  描述：

  2-(2-乙基苯基)乙腈 在 alkaline hydrogen peroxide 作用下， 生成 2-(2-ethylphenyl)acetic acid
  参考文献：
  名称：

  Mayer; English, Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 75

  摘要：

  DOI：

文献信息

• Heterocycles as nicotinic acid receptor agonists for the treatment of dyslipidemia
  申请人：Palani Anandan

  公开号：US20060264489A1

  公开（公告）日：2006-11-23

  A compound having the general structure of Formula (I): or a pharmaceutically acceptable salt, solvate, ester, or tautomer thereof, wherein: Q is selected from the group consisting of: and L is selected from the group consisting of: or a pharmaceutically acceptable salt, solvate, ester, or tautomer thereof, are useful in treating diseases, disorders, or conditions such as metabolic syndrome and dyslipidemia.

  具有通式（I）的一种化合物： 或其药学上可接受的盐、溶剂化合物、酯或互变异构体，其中： Q选自以下群组： 和 L选自以下群组： 或其药学上可接受的盐、溶剂化合物、酯或互变异构体，可用于治疗代谢综合征和血脂异常等疾病、疾患或症状。
• Aromatic Claisen Rearrangements of Benzyl Ketene Acetals: Conversion of Benzylic Alcohols to ( <i>ortho</i> ‐Tolyl)acetates
  作者：Jed M. Burns、Elizabeth H. Krenske、Ross P. McGeary

  DOI：10.1002/ejoc.201601354

  日期：2017.1.10

  Claisen rearrangements of benzyl vinyl ethers are much less facile than those of aliphatic allyl vinyl ethers, and their synthetic utility has remained relatively unexplored. A one-pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α-alkoxy substituent on the vinyl group. A [3,3]-sigmatropic mechanism was supported by trapping of the

  苄基乙烯基醚的克莱森重排远不如脂肪族烯丙基乙烯基醚的克莱森重排容易，并且它们的合成效用仍然相对未开发。据报道，一锅法用于生成和克莱森重排苄基乙烯基醚，在乙烯基上含有活化的 α-烷氧基取代基。通过在分子内 Alder-ene 反应中捕获中间体异甲苯来支持 [3,3]-σ 机制。
• Synthesis and Preliminary Biological Characterization of New Semisynthetic Derivatives of Ramoplanin
  作者：Romeo Ciabatti、Sonia I. Maffioli、Gianbattista Panzone、Augusto Canavesi、Elena Michelucci、Paolo S. Tiseni、Ettore Marzorati、Anna Checchia、Matteo Giannone、Daniela Jabes、Gabriella Romanò、Cristina Brunati、Gianpaolo Candiani、Franca Castiglione

  DOI：10.1021/jm070042z

  日期：2007.6.1

  of the new ramoplanin derivatives showed antimicrobial activity similar to that of the natural precursor coupled with a significantly improved local tolerability. Among them the derivative in which the 2-methylphenylacetic acid has replaced the di-unsaturated fatty acid side chain (48) was selected as the most interesting compound and submitted to further in vitro and in vivo characterization studies

  雷莫拉宁是一种糖脂肽肽抗生素，对革兰氏阳性细菌（包括耐万古霉素的肠球菌）具有活性。雷莫拉宁通过不同于糖肽的机制抑制细菌细胞壁的生物合成，因此对这些抗生素没有交叉耐药性。到目前为止，由于静脉内注射时局部耐受性低，因此一直无法阻止雷莫拉汀的全身使用。为了克服这个问题，选择性去除了拉莫普林的脂肪酸侧链，并用各种不同的羧酸代替。许多新的雷莫拉宁衍生物显示出与天然前体相似的抗微生物活性，并具有明显改善的局部耐受性。
• Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety
  作者：Jin Xie、Fengzhi Yang、Man Zhang、Celine Lam、Yixue Qiao、Jia Xiao、Dongdong Zhang、Yuxuan Ge、Lei Fu、Dongsheng Xie

  DOI：10.1016/j.bmcl.2016.12.007

  日期：2017.1

  A series of CAPE derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2′-position of phenylethanol moiety

  合成了一系列具有单取代苯基乙醇部分的CAPE衍生物，并通过MTT分析对4种人类癌细胞系（Hela，DU-145，MCF-7和ECA-109）的生长进行了评估。首次系统地研究了取代基对抗增殖活性的影响。发现苯乙醇部分的2'-位的给电子和疏水取代基可以显着增强CAPE的抗增殖活性。作为一种新型咖啡酸酯的2'-丙氧基衍生物表现出出色的效力（ 分别针对Hela和DU-145的IC 50 = 0.4±0.02和0.6±0.03μM）。
• Visible-Light-Induced C–O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones
  作者：Honggu Im、Dahye Kang、Soyeon Choi、Sanghoon Shin、Sungwoo Hong

  DOI：10.1021/acs.orglett.8b03166

  日期：2018.12.7

  Visible-light-induced intramolecular C–O bond formation was developed using 2,4,6-triphenylpyrylium tetrafluoroborate (TPT), which allows the regiocontrolled construction of cyclic ethers and lactones. The reaction is likely to proceed through the single-electron oxidation of the phenyl group, followed by the formation of a benzylic radical, thus preventing a competing 1,5-hydrogen abstraction pathway

  可见光诱导的分子内C-O键的形成是使用2,4,6-三苯基吡啶鎓四氟硼酸酯（TPT）进行的，该化合物可进行区域控制的环醚和内酯的构建。该反应可能通过苯基的单电子氧化进行，然后形成苄基，从而阻止竞争的1,5-氢提取途径。详细的机理研究表明，分子氧可用于捕获自由基中间体以形成苯甲醇，然后将其进行环化。通过使用统一协议提供对有价值的五元和六元环醚和内酯的有效访问，此新方法可作为强大的平台。