2-(2,6-二甲基苯氧基)乙醇 | 16737-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(2,6-二甲基苯氧基)乙醇
• 英文名称: 2-(2,6-dimethylphenoxy)ethanol
• 英文别名: 2,6-dimethylphenoxyethanol；2-(2,6-dimethylphenyloxy)ethanol；2-(2,6-Dimethyl-phenoxy)-etahnol；2-(2,6-Dimethylphenoxy)ethan-1-ol
• CAS: 16737-71-6
• 化学式: C₁₀H₁₄O₂
• mdl: MFCD11613988
• 分子量: 166.22
• InChiKey: DYTSLGCVWCVGLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,6-二甲基苯氧基)乙醇 在 三溴化磷 作用下， 以53%的产率得到2-(2-溴乙氧基)-1,3-二甲基苯
  参考文献：
  名称：

  Marona, Henryk; Antkiewicz-Michaluk, Lucyna, Acta poloniae pharmaceutica, 1998, vol. 55, # 6, p. 487 - 498

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 甲醇 、 氢氧化钾 、 4-甲基苯磺酸吡啶 作用下， 以 二甲基亚砜 为溶剂， 反应 32.08h， 生成 2-(2,6-二甲基苯氧基)乙醇
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Aryloxyethyl Thiocyanate Derivatives against Trypanosoma cruzi

  摘要：

  As a continuation of our project aimed at the search for new and safe chemotherapeutic and chemoprophylactic agents against American trypanosomiasis (Chagas' disease), several drugs structurally related to 4-phenoxyphenoxyethyl thiocyanate (4) were designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible for this disease, the hemoflagellated protozoan Trypanosoma cruzi. This thiocyanate derivative was previously shown to be an effective and potent agent against T. cruzi proliferation. Several drugs possessing thiocyanate groups proved to be effective growth inhibitors of T. cruzi growth. Among the designed compounds, it is important to point out the extremely potent activity shown by 11, 23, 38, 53, 90, 99, and 117 against the epimastigote forms of the parasite. All of them exhibited IC50 values in the low micromolar range, and these values were comparable with those presented by our lead drug 4 and ketokonazole, a well-known antiparasitic agent. The activity displayed by the nitrogen-containing derivative 90 was very promising with IC50 values of 3.3 muM. Several other thiocyanate derivatives also proved to be very potent inhibitors of the multiplication of T. cruzi epimastigotes, such as compounds 28, 33, 43, 48, 56, 61, 66, 71, 76, and 124. Compound 43 resulted in being a promising drug because it was also very effective against amastigotes, the clinically more relevant form of the parasite. This compound was Mold more potent than 4, while 11 showed nearly the same activity as our lead drug against intracellular T. cruzi. It was very surprising that the experimental juvenoid 124, although fairly devoid of activity against epimastigotes, was very effective against intracellular amastigotes growing in myoblasts. The rest of the designed compounds showed a broad degree of inhibitory action, from moderately active drugs to drugs almost devoid of antiparasitic activity. Compound 43 is an interesting example of an effective antichagasic agent that presents excellent prospectives not only as a lead drug but also to be used for further in vivo studies.

  DOI：

  10.1021/jm0201518

文献信息

• Microwave Mediated Protection of Hindered Phenols and Alcohols
  作者：Tejas Pothi、Mahesh Dawange、Kamlesh Chavan、Rajiv Sharma、Nabajyoti Deka

  DOI：10.5012/jkcs.2012.56.6.706

  日期：2012.12.20

  Hindered phenols and alcohols were protected as their corresponding ethers using different alkylating agents in presence of KOH/DMSO under microwave irradiation. $$R-OH\;KOH/DMSO,\;R^\prime}-X,\;MW \\\vec10-15\;Mins,\;80%-90%\;Yield}}}\;R^/}^O\backslash}}R^\prime}$$.

  在微波照射下，使用不同的烷基化试剂，在KOH/DMSO的存在下，将 hindered 酚和醇保护为其相应的醚。$$R-OH\;KOH/DMSO,\;R^\prime}-X,\;MW \\\vec10-15\;Mins,\;80%-90%\;Yield}}}\;R^/}^O\backslash}}R^\prime}$$.
• Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP1170275A3

  公开（公告）日：2004-04-14

  Normally liquid, omega-hydrofluoroalkyl ether compounds (and selected mixtures thereof) have a saturated perfluoroaliphatic chain of carbon atoms interrupted by one or more ether oxygen atoms. The compounds can be prepare, e.g. by decarboxylation of the corresponding fluoroalkyl ether carboxylic acids and are useful, e.g., in cleaning and drying applications.

  通常是液体的ω-氢氟烷基醚化合物（及其选定的混合物）具有由一个或多个醚氧原子中断的饱和全氟脂肪链的碳原子。这些化合物可以通过相应的氟烷基醚羧酸的脱羧反应制备，例如在清洁和干燥应用中很有用。
• Copper(ii)-catalyzed C–O coupling of aryl bromides with aliphatic diols: synthesis of ethers, phenols, and benzo-fused cyclic ethers
  作者：Yajun Liu、Se Kyung Park、Yan Xiao、Junghyun Chae

  DOI：10.1039/c4ob00649f

  日期：——

  copper-catalyzed C–O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(II) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers

  使用更便宜，更有效且易于去除的铜（II）催化剂，开发了一种高效的铜催化的芳基溴化物与脂肪族二醇之间的C-O交叉偶联反应。使用5 mol％的CuCl 2和3当量的K 2 CO 3将宽范围的芳基溴化物与不同长度的脂肪族二醇偶联在不存在任何其他配体或溶剂的情况下，以良好或优异的收率得到相应的羟烷基芳基醚。在这个新开发的方案中，脂族二醇具有多方面的功能，如偶联反应物，配体和溶剂。所得的羟烷基芳基醚进一步容易地转化成相应的苯酚，为从芳基溴化物得到的苯酚提供了一种有价值的替代方法。此外，已证明它们是用于更高级分子如苯并呋喃和苯并稠合的环醚的有用中间体。
• β-Hydroxyalkylation of sterically hindered phenols with epoxides in acid medium
  作者：A. P. Krysin、S. A. Amitina、T. G. Egorova、V. G. Vasiliev

  DOI：10.1134/s1070363211020125

  日期：2011.2

  HPLC-MS method the directions of the side reactions were explored. The method has been successfully tested in a pilot installation. With 2,6-dimethylphenol instead of 2,6-di-tert-butylphenol a sharp increase occurs in the content of ethers in the reaction product. With epichlorohydrin, 2,6-di-tert-butylphenol affords a product, which is easily converted into an epoxide containing a sterically hindered phenol

  2，6-二烷基苯酚与环氧乙烷，环氧丙烷和环氧氯丙烷在SnCl 4存在下于-5至+ 5°C的温度反应，会导致相应的苯酚在β的β位上形成羟基。对位取代基的脂族链。确定了2，6-二叔丁基苯酚与环氧乙烷反应的最大选择性的条件。通过HPLC-MS方法探索了副反应的方向。该方法已在试验安装中成功测试。用2，6-二甲基苯酚代替2，6-二叔丁基苯酚，反应产物中醚的含量急剧增加。含表氯醇，2,6-二酯叔丁基苯酚提供了一种产物，该产物易于转变成在其结构中含有空间位阻酚的环氧化物。
• METHOD FOR PRODUCING FLUORENE DERIVATIVE
  申请人：Fujii Katsuhiro

  公开号：US20120029244A1

  公开（公告）日：2012-02-02

  A method for producing a fluorene derivative by reacting fluorenone with a phenol or a phenoxyalcohol in the presence of an acid catalyst includes: adding an alkali to an obtained reaction liquid containing a fluorene derivative; and concentrating a resultant mixture liquid without removing the alkali thus added and a reaction product of the alkali, thereby separating an unreacted phenol or unreacted phenoxyalcohol.

  一种制备芴衍生物的方法，通过在酸催化剂存在下将芴酮与苯酚或苯氧乙醇反应，包括以下步骤：向含有芴衍生物的反应液中加入碱；在不去除已添加的碱和碱的反应产物的情况下浓缩混合液，从而分离未反应的苯酚或未反应的苯氧乙醇。