2-(2-溴-苯氧基)-乙醇 | 34743-89-0

• 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-溴-苯氧基)-乙醇
• 英文名称: 2-(2-bromophenoxy)ethanol
• 英文别名: 2-bromophenoxyethanol；2-(2-bromophenoxy)ethan-1-ol
• CAS: 34743-89-0
• 化学式: C₈H₉BrO₂
• mdl: MFCD11147863
• 分子量: 217.062
• InChiKey: KKLBXMUYKQBAAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909499000
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2-(2-溴-苯氧基)-乙醇 在 (4,4′-di-tert-butyl-2,2′-dipyridyl)Ni(o-tolyl)(Br) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以86%的产率得到1,4-苯并二恶烷
  参考文献：
  名称：

  光促进的镍催化：NiII-芳基配合物催化的醇与芳基亲电试剂的醚化。

  摘要：

  据报道，（杂）芳基亲电试剂与伯醇和仲醇的高效C-O偶联反应。在可溶性胺碱的存在下，在没有任何其他光敏剂的情况下，在长波紫外线（390–395 nm）辐射下，由Ni II-芳基络合物催化，该反应可以使芳基溴化物和芳基氯化物以及磺酸盐与多种伯和仲脂族醇，可提供合成上重要的醚。分子内CO偶联也是可能的。该反应似乎通过Ni I -Ni III催化循环进行。

  DOI：

  10.1002/anie.202003359
• 作为产物：
  描述：

  2-bromophenoxyethyl tetrahydro-2H-pyran-2-yl ether 在 甲醇 、 4-甲基苯磺酸吡啶 作用下， 反应 16.0h， 以72%的产率得到2-(2-溴-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

• Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles
  作者：Steven Frippiat、Christine Baudequin、Christophe Hoarau、Antoine Peresson、Thibaut Perse、Yvan Ramondenc、Cédric Schneider、Olivier Querolle、Patrick Angibaud、Virginie Poncelet、Lieven Meerpoel、Vincent Levacher、Laurent Bischoff

  DOI：10.1055/s-0040-1708003

  日期：2020.6

  The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles

  通过分子间和分子内途径描述了钯催化的 N-取代甲基咪唑-4-羧酸酯的芳基化和烯基化。在低极性 1,4-二恶烷溶剂中，直接 C2-H 和 C5-H 芳基化和烯基化分别在 Pd(0)/Cu(I) 协同催化和 Pd(0) 催化下进行。该方法可以获得 C2（杂）芳基或烯基咪唑以及具有五至七元中间环的创新 C2-和 C5-芳基化的稠合咪唑三环。
• FLAP MODULATORS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：US20150259357A1

  公开（公告）日：2015-09-17

  The present invention relates to compounds of Formula (I), or a form thereof, wherein ring A, R 1 , R 2 , R 3 , R 3 ′, L, W, and V are as defined herein, useful as FLAP modulators. The invention also relates to pharmaceutical compositions comprising compounds of Formula (I). Methods of making and using the compounds of Formula (I) are also within the scope of the invention

  本发明涉及式（I）的化合物，或其形式，其中环A，R1，R2，R3，R3'，L，W和V如本文所定义，可用作FLAP调节剂。该发明还涉及包含式（I）化合物的药物组合物。制备和使用式（I）化合物的方法也属于本发明的范围。
• Revisiting Hydroxyalkylation of Phenols with Cyclic Carbonates
  作者：Shih‐Chieh Kao、Yi‐Ching Lin、Ilhyong Ryu、Yen‐Ku Wu

  DOI：10.1002/adsc.201900287

  日期：2019.8.5

  fluoride‐mediated hydroxyalkylation reaction of phenols with cyclic carbonates. This operationally simple method enables the synthesis of a variety of aryl β‐hydroxyethyl ethers in good to excellent yields with a very small amount of catalyst loading (0.1–1 mol%). Of particular note is the efficient conversion of aromatic diols and phloroglucinol to the corresponding bis‐ and tris‐hydroxyethylated products. To further

  描述了四丁基氟化铵介导的酚与环状碳酸酯的羟烷基化反应。这种操作简单的方法能够以很小的催化剂负载量（0.1–1 mol％）以良好的产率和优异的产率合成多种芳基β-羟乙基醚。特别值得注意的是芳族二醇和间苯三酚可有效地转化为相应的双和三羟乙基化产物。为了进一步展示该方案的多功能性，愈创甘油醚通过愈创木酚和碳酸甘油酯的缩合一步制备。我们还开发了一种流式乙氧基化工艺，可以连续合成多元醇。
• [EN] DIHYDROBENZOXAZINE AND TETRAHYDROQUINOXALINE SODIUM CHANNEL INHIBITORS<br/>[FR] INHIBITEURS DES CANAUX SODIQUES DE TYPE DIHYDROBENZOXAZINE ET TÉTRAHYDROQUINOXALINE
  申请人：AMGEN INC

  公开号：WO2013122897A1

  公开（公告）日：2013-08-22

  The present invention provides compounds of Formula I, or pharmaceutically acceptable salts thereof, that are inhibitors of voltage-gated sodium channels, in particular Nav 1.7. The compounds are useful for the treatment of diseases treatable by inhibition of sodium channels such as pain disorders. Also provided are pharmaceutical compositions containing compounds of the present invention.

  本发明提供了式I的化合物或其药学上可接受的盐，这些化合物是电压门控钠通道的抑制剂，特别是Nav 1.7。这些化合物对于治疗可通过抑制钠通道治疗的疾病，如疼痛障碍，是有用的。还提供了含有本发明化合物的药物组合物。
• Synthesis of Tetrasubstituted Alkenes through a Palladium-Catalyzed Domino Carbopalladation/CH-Activation Reaction
  作者：Lutz F. Tietze、Tim Hungerland、Alexander Düfert、Ina Objartel、Dietmar Stalke

  DOI：10.1002/chem.201103209

  日期：2012.3.12

  Helical tetrasubstituted alkenes (7) were obtained in a highly efficient way through a palladium‐catalyzed domino‐carbopalladation/CH‐activation reaction of propargylic alcohols 6 in good to excellent yields. Electron‐withdrawing‐ and electron‐donating substituents can be introduced onto the upper and lower aromatic rings. The substrates (6) for the domino process were synthesized by addition of the

  螺旋四取代的烯烃（7）是通过钯催化的炔丙醇6的多米诺-卡铂钯化/ CH活化反应高效而良好地获得的。吸电子和供电子取代基可以引入到上和下芳环上。通过将锂化炔烃（20）添加到各种醛（19）中，合成了用于多米诺工艺的基材（6）；此外，通过使用Noyori方法还原相应的酮，底物可对映选择性地（在95％ee中）到达。