1-(4-bromophenoxy)propan-2-ol | 65387-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-bromophenoxy)propan-2-ol
• 英文别名: 1-(4'-Bromophenoxy)-propane-2-ol
• CAS: 65387-46-4
• 化学式: C₉H₁₁BrO₂
• 分子量: 231.089
• InChiKey: BXMXMTJFBNXCTN-UHFFFAOYSA-N

物化性质

• 沸点：
  129-136 °C(Press: 4 Torr)
• 密度：
  1.4496 g/cm3

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：
  0.33
• 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：

  1-(4-bromophenoxy)propan-2-ol 在 对甲苯磺酰氯 、 sodium azide 作用下， 以 甲醇 为溶剂， 生成 1-(4-溴苯氧基)-2-丙酮
  参考文献：
  名称：

  Pharmacological profiling of JME-173, a novel mexiletine derivative combining dual anti-inflammatory/anti-spasmodic functions and limited action in Na+ channels

  摘要：

  Existing evidence suggests that the local anaesthetic mexiletine can be beneficial for patients with asthma. However, caution is required since anaesthesia of the airways inhibits protective bronchodilator neuronal reflexes, limiting applications in conditions of hyperirritable airways. Here, we describe the synthesis of a new series of mexiletine analogues, which were screened for reduced activity in Na+ channels and improved smooth muscle relaxant effects, that were evaluated using the patch-clamp technique and an isolated tracheal organ bath, respectively. JME-173 (1-(4-bromo-3,5-dimethylphenoxy)propan-2-amine) was the most effective among the four mexiletine analogues investigated. JME-173 was then studied in vivo using a murine model of lung inflammation induced by cigarette smoke (CS) and in vitro using neutrophil chemotaxis and mast cell degranulation assays. Finally, the JME-173 pharmacokinetic profile was assessed using HPLC-MS/MS bioanalytical method. JME-173 directly inhibited IL-8 (CXCL8)- and FMLP-induced human neutrophil chemotaxis and allergen-induced mast cell degranulation. After oral administration 1 h before CS exposure, JME-173 (50 mg/kg) strongly reduced the increased number of macrophages and neutrophils recovered in the bronchoalveolar effluent without altering lymphocyte counts. Pharmacokinetic experiments of JME-173 (10 mg/kg, orally) showed values of maximum concentration (C-max), maximum time (T-max), area under the blood concentration-time curve (AUC(0-t)) and area under the blood concentration-time curve from 0-Inf (AUC(0-inf)) of 163.3 + 38.3 ng/mL, 1.2 +/- 0.3 h, 729.4 +/- 118.3 ng*h/ml and 868.9 + 117.1 ng*h/ml (means + S.E.M.), respectively. Collectively, these findings suggest that JME-173 has the potential to be an effective oral treatment for diseases associated with bronchoconstriction and inflammation.

  DOI：

  10.1016/j.ejphar.2020.173367
• 作为产物：
  描述：

  1-(4-溴苯氧基)-2-丙酮 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 生成 1-(4-bromophenoxy)propan-2-ol
  参考文献：
  名称：

  选择性交叉脱氢C（sp3）-H与芳烃的芳基化。

  摘要：

  选择性的C（sp3）-C（sp2）键结构是化学合成中的主要关注点。尽管经典的交叉偶联反应成功，但惰性C（sp3）-H和C（sp2）-H键之间的交叉脱氢偶联代表了对新C（sp3）-C（sp2）键的有吸引力的替代选择。在本文中，我们建立了醇与非定向芳烃的选择性分子间和分子内C（sp3）-H芳基化反应，从而提供了访问广泛的β-芳基化醇的一般途径，包括四氢萘-2-醇和苯并吡喃-3-具有高至优异的化学和区域选择性的醇。

  DOI：

  10.1021/acs.orglett.0c00588

文献信息

• [EN] MAP4K4 INHIBITORS<br/>[FR] INHIBITEURS DE MAP4K4
  申请人：IMPERIAL INNOVATIONS LTD

  公开号：WO2019073253A1

  公开（公告）日：2019-04-18

  This invention relates to pyrrolopyrimidine comprising compounds that may be useful as inhibitors of Mitogen-activated Protein Kinase Kinase Kinase Kinase-4 (MAP4K4). The invention also relates to the use of these pyrrolopyrimidine comprising compounds, for example in a method of treatment. There are also provided processes for producing compounds of the present invention and method of their use. In particular, the present invention relates to compounds of formula (I).

  这项发明涉及含有吡咯吡嘧啶的化合物，这些化合物可能作为丝裂原活化蛋白激酶激酶激酶激酶-4（MAP4K4）的抑制剂而有用。该发明还涉及利用这些含有吡咯吡嘧啶的化合物，例如在治疗方法中的使用。还提供了生产本发明化合物的方法以及它们的使用方法。具体而言，本发明涉及式（I）的化合物。
• Complex catalyst, process for producing the complex catalyst, and process for producing alchohol derivative with the complex catalyst
  申请人：——

  公开号：US20040077487A1

  公开（公告）日：2004-04-22

  There are provided (asymmetric) complex catalysts comprising metal complexes and Lewis acids as components, the metal complex being of formula (1): 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are the same or different and are independently hydrogen, halogen, alkyl or the like; one of R 9 and R 10 is hydrogen and the other is alkyl of 1 to 4 carbon atoms or the like; Q is a single bond or alkylene of 1 to 4 carbon atoms; M is a metal ion; and A is a balancing counter ion or ligand; processes for the production of these complex catalysts; processes for the production of (optically active) alcohol derivatives, characterized in that cyclic ether compounds are reacted with phenol derivatives in the presence of these complex catalysts; and further processes for producing (optically active) nitrogen-containing heterocyclic compounds by reacting these alcohol derivatives with halogenated nitrogen-containing heterocyclic compounds in the presence of a base.

  提供了由金属配合物和路易斯酸组成的（不对称的）复杂催化剂，其中金属配合物的化学式为（1）：1其中R1、R2、R3、R4、R5、R6、R7和R8相同或不同，独立地是氢、卤素、烷基或类似物；R9和R10中的一个是氢，另一个是1至4个碳原子的烷基或类似物；Q是单键或1至4个碳原子的烷基；M是金属离子；A是平衡的反离子或配体；制备这些复杂催化剂的方法；制备（光学活性的）醇衍生物的方法，其特征在于在这些复杂催化剂的存在下，环氧化合物与酚衍生物反应；以及在碱的存在下，通过将这些醇衍生物与卤素化的含氮杂环化合物反应，制备（光学活性的）含氮杂环化合物的进一步方法。
• Novel derivatives of 1,3-diphenoxypropane-2-on, process of their
  申请人：Klingepharma GmbH & Co.

  公开号：US04189594A1

  公开（公告）日：1980-02-19

  Compounds of the formula ##STR1## wherein R.sup.1 is Cl, Br, CH(CH.sub.3).sub.2 or C(CH.sub.3).sub.3 ; A is a single bond, --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; and R.sup.2 is H, the cation of a pharmaceutically acceptable salt or an alkyl of up to three carbons, are strong hypolipaemic agents.

  公式为##STR1##的化合物，其中R.sup.1为Cl，Br，CH（CH.sub.3）.sub.2或C（CH.sub.3）.sub.3; A为单键，--CH.dbd.CH--或--CH.sub.2--CH.sub.2--; R.sup.2为H，药学上可接受的盐阳离子或最多三个碳的烷基，是强的降脂剂。
• Catalytic reductive ring opening of epoxides enabled by zirconocene and photoredox catalysis
  作者：Kazuhiro Aida、Marina Hirao、Aiko Funabashi、Natsuhiko Sugimura、Eisuke Ota、Junichiro Yamaguchi

  DOI：10.1016/j.chempr.2022.04.010

  日期：2022.6

  The reductive ring opening of epoxides is a powerful transformation to convert readily accessible epoxides into a diverse array of valuable alcohols, including pharmaceuticals, agrochemicals, and functional polymers. Although significant progress has been made, the established methods were limited to titanocene-catalyzed reactions. Herein, we report an unprecedented zirconocene-catalyzed ring opening

  环氧化物的还原性开环是一种强大的转化，可将容易获得的环氧化物转化为各种有价值的醇，包括药物、农用化学品和功能性聚合物。尽管已经取得了重大进展，但已建立的方法仅限于二茂钛催化反应。在此，我们报告了一种前所未有的由光氧化还原催化实现的由锆茂催化的环氧化物开环。与传统的开环方法相比，本方案表现出反向区域选择性，可通过假定的不太稳定的自由基提供更多的取代醇。该反应非常温和，可以顺利切割具有多种官能团的分子中的 C-O 键，包括天然产物。
• METHOD FOR PRODUCING OPTICALLY ACTIVE ALCOHOL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1982972A1

  公开（公告）日：2008-10-22

  A method for producing an optically active alcohol compound comprising reacting a cyclic ether compound with a phenol compound in the presence of an asymmetric complex obtained by reacting an optically active metal complex represented by the formula (1): wherein R1, R2, R3, R4, R5, R6, R7 and R8 are the same or different and each independently represent a hydrogen atom, an alkyl group or the like; one of R9 and R10 is a hydrogen group and the other is a substituted or unsubstituted phenyl group or the like; Q represents a single bond, a C1-C4 alkylene group or the like; M represents a metal ion; and when an ionic valency of the metal ion is same as a coordination number of a ligand, A is nonexistent, and when the above-mentioned ionic valency is different from the coordination number, and A represents a counter ion or a ligand, with a zirconium alkoxide or a hafnium alkoxide.

  一种生产光学活性醇化合物的方法，包括在由式（1）表示的光学活性金属络合物反应得到的不对称络合物存在下，使环醚化合物与苯酚化合物反应： 其中 R1、R2、R3、R4、R5、R6、R7 和 R8 相同或不同，且各自独立地代表氢原子、烷基或类似基团； R9 和 R10 中的一个是氢基，另一个是取代或未取代的苯基或类似基团； Q 代表单键、C1-C4 亚烷基或类似物； M 代表金属离子；当金属离子的离子价与配体的配位数相同时，A 不存在，当上述离子价与配位数不同时，A 代表金属离子。 当上述离子价与配位数不同，且 A 代表反离子或配体时，用氧化锆或氧化铪。