5-溴-2-甲氧基间苯二酚 | 133932-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-溴-2-甲氧基间苯二酚
• 英文名称: 5-bromo-2-methoxybenzene-1,3-diol
• 英文别名: 4-bromo-2,6-dihydroxyanisole；5-bromo-2-methoxy-1,3-benzenediol；5-Brom-2-methoxyresorcinol；5-bromo-2-methoxy-resorcinol；5-Bromo-2-methoxyresorcinol
• CAS: 133932-61-3
• 化学式: C₇H₇BrO₃
• 分子量: 219.035
• InChiKey: SXXALXBGJPYMSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126°C
• 溶解度：
  可溶于二氯甲烷、乙醇、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-溴-2-甲氧基间苯二酚 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以99%的产率得到2-甲氧基间苯二酚
  参考文献：
  名称：

  OPPI Briefs Hydrangetin 和Collbsin 的新合成

  摘要：

  Hydrrangetin (6) 是许多植物物种的天然成分，包括 Hydrangea macrophylla'2 和 Zanthoxylum schinifolium? Collinin (7) 存在于绣球花、'*2 Zanthoxylum s~hinifolium、~ Flindersia ~ ollina 、~ Flindersia mculata' 和 Haplophyllum alberti-regelk6 等中。血小板聚集 3s7 和抗乙型肝炎病毒的活性。这些有趣的特性使这种香豆素成为有机合成的有用目标。已经报道了以连苯三酚和丙炔酸为原料合成 collinin 的方法。8 我们现在描述了一种以现成的 2,4,6-三溴茴香醚 (2) 为原料的 collinin (7) 的替代合成策略。该途径还提供了一条合成绣球花素的新途径 (6)。2,4, 通过 2,4,6-三溴苯酚 1 与 1 当量硫酸二甲酯和

  DOI：

  10.1080/00304940709458594
• 作为产物：
  描述：

  2,4,6-三溴苯甲醚 在 正丁基锂 、 硼酸三甲酯 作用下， 以 正戊烷 、 溶剂黄146 为溶剂， 反应 1.25h， 以89%的产率得到5-溴-2-甲氧基间苯二酚
  参考文献：
  名称：

  OPPI Briefs Hydrangetin 和Collbsin 的新合成

  摘要：

  Hydrrangetin (6) 是许多植物物种的天然成分，包括 Hydrangea macrophylla'2 和 Zanthoxylum schinifolium? Collinin (7) 存在于绣球花、'*2 Zanthoxylum s~hinifolium、~ Flindersia ~ ollina 、~ Flindersia mculata' 和 Haplophyllum alberti-regelk6 等中。血小板聚集 3s7 和抗乙型肝炎病毒的活性。这些有趣的特性使这种香豆素成为有机合成的有用目标。已经报道了以连苯三酚和丙炔酸为原料合成 collinin 的方法。8 我们现在描述了一种以现成的 2,4,6-三溴茴香醚 (2) 为原料的 collinin (7) 的替代合成策略。该途径还提供了一条合成绣球花素的新途径 (6)。2,4, 通过 2,4,6-三溴苯酚 1 与 1 当量硫酸二甲酯和

  DOI：

  10.1080/00304940709458594

文献信息

• TUBULIN BINDING AGENTS
  申请人：The Provost, Fellows, Foundation Scholars, & the other Members of Board, of the College of the Holy

  公开号：US20150018566A1

  公开（公告）日：2015-01-15

  The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.

  该发明提供了类似于康柏他定A-4的化合物，经过改良以增强微管结合活性，在某些实施例中还具有促进在进行血管生成的血管系统中积聚（归巢活性）的能力。这些化合物基于康柏他定A-4的骨架结构，其具有一个微管结合药效团，包括两个融合环（A环和B环），其中B环被取代为（a）芳香环结构（C环）和（b）从B环上脱落的第二取代基/官能团。芳香环结构通常是一个六元环酚或苯胺结构，也可以是一个融合环结构，如取代或未取代的萘。B环上的第二取代基可以是已知可提供增强微管结合活性的取代基（例如酰基），也可以是促进B环官能化的取代基（例如羟基或胺基），或者可以是一种针对在进行血管生成的血管系统上优先表达而在静止血管系统上不表达的靶标的结合剂。
• Tuning the Molecular Packing of Self‐Assembled Amphiphilic Pt ^II Complexes by Varying the Hydrophilic Side‐Chain Length
  作者：Lorena Herkert、Philipp Selter、Constantin G. Daniliuc、Nils Bäumer、Jasnamol P. Palakkal、Gustavo Fernández、Michael Ryan Hansen

  DOI：10.1002/chem.202003445

  日期：2021.3.8

  constitutes one of the major challenges in self‐assembly and is essential for the preparation of functional materials. Herein, we have achieved high precision control over the supramolecular packing of amphiphilic PtII complexes by systematic variation of the hydrophilic side‐chain length. A novel approach of general applicability based on complementary X‐ray diffraction and solid‐state NMR spectroscopy

  理解分子设计和填充模式之间的关系是自组装的主要挑战之一，对于功能材料的制备至关重要。在这里，我们已经实现了对两亲性Pt II的超分子堆积的高精度控制通过亲水性侧链长度的系统变化形成复合物。一种基于互补X射线衍射和固态NMR光谱的通用性新颖方法，使我们能够在分子特征和超分子有序之间建立明确的关联。系统地增加侧链的长度会逐渐增加空间需求，并减少芳族相互作用的程度，从而导致分子堆积从平行结构向长滑结构逐渐转变。值得注意的是，我们的发现强调了先进的固态NMR技术对于获取不可能单晶生长的超分子系统的结构信息的必要性。二和芳香分子。
• Enantioselective Total Synthesis of (−)-Misramine
  作者：Keisuke Yoshida、Yuta Fujino、Yusei Takamatsu、Kohei Matsui、Akihiro Ogura、Yuri Fukami、Shinji Kitagaki、Ken-ichi Takao

  DOI：10.1021/acs.orglett.8b02198

  日期：2018.8.17

  The enantioselective total synthesis of an unusual pentacyclic proaporphine alkaloid, (−)-misramine, was achieved. The synthetic strategy relied on an enantioselective intramolecular Friedel–Crafts-type 1,4-addition using an asymmetric organocatalyst to construct a spiroindane skeleton containing an all-carbon quaternary stereocenter and a double reductive amination of the keto-aldehyde to form a piperidine

  实现了一种不寻常的五环前胃啡肽生物碱（-）-misramine的对映选择性全合成。合成策略依赖于对映选择性分子内Friedel-Crafts型1,4-加成反应，该反应使用不对称有机催化剂来构建含有全碳四元立体中心的螺茚满骨架，并通过酮醛的双还原胺化反应形成哌啶环。综合结束。这项工作是前啡肽生物碱的不对称合成的第一个例子。
• An improved process for the preparation of 5-bromo-2-methoxyresorcinol
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0471941A2

  公开（公告）日：1992-02-26

  This invention is concerned with an improved process for metallating 2,4,6-tribromoanisole 1 and reacting this intermediate lithio species with various electrophiles for example the trialkoxy borates which an example is trimethylborate, the improvement comprising carrying out the reaction under heterogenous conditions. This product is oxidatively converted to the compound 5-bromo-2-methoxy-resorcinol 2, which is in turn converted to the known 2-methoxy-resorcinol 3. The process and intermediate are useful in the synthesis of platelet activating factor antagonist thiazolium, 3-[[3-[[hydroxy[2-methoxy-3-(tetradecyloxy) phenoxy]phosphinyl]oxy]phenyl]methyl]-5-methyl-, hydroxide, inner salt CA of U. S. Patent 4983592 (1991).

  本发明涉及一种改进的2,4,6-三溴苯甲醚1金属化过程，并将此中间体锂化物与各种亲电试剂反应，例如三烷氧基硼酸盐，其中一种示例是三甲基硼酸盐，改进包括在异相条件下进行反应。将该产品氧化转化为化合物5-溴-2-甲氧基邻苯二酚2，然后再将其转化为已知的2-甲氧基邻苯二酚3。该过程和中间体在合成血小板活化因子拮抗剂噻唑盐，3-[[3-[[羟基[2-甲氧基-3-(四十四烷氧基)苯氧基]膦酰基]氧基]苯基]甲基]-5-甲基-, 内盐CA的合成中有用。该合成已在美国专利4983592（1991年）中得到描述。
• Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor
  作者：A. Wissner、M. L. Carroll、K. E. Green、S. S. Kerwar、W. C. Pickett、R. E. Schaub、L. W. Torley、S. Wrenn、C. A. Kohler

  DOI：10.1021/jm00087a023

  日期：1992.5

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on rabbit platelets. These in vitro data were compared to similar data obtained for a number of known PAF antagonists. The compounds were evaluated in vivo, in both the mouse and rabbit, for their ability to prevent death induced by a lethal challenge of PAF. The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.