1-(溴甲基)-2,5-二甲氧基-3,4,6-三甲基苯 | 117574-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(溴甲基)-2,5-二甲氧基-3,4,6-三甲基苯
• 英文名称: 1-(bromomethyl)-2,5-dimethoxy-3,4,6-trimethylbenzene
• CAS: 117574-75-1
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: RRAYNZOCAVZGKV-UHFFFAOYSA-N

物化性质

• 熔点：
  71-72 °C(Solv: methanol (67-56-1))
• 沸点：
  331.0±37.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(溴甲基)-2,5-二甲氧基-3,4,6-三甲基苯 在 ammonium cerium(IV) nitrate 、 四甲基乙二胺 、 氧气 、 copper(l) chloride 作用下， 以 乙二醇二甲醚 、 乙醚 、 水 、 乙腈 为溶剂， 反应 24.75h， 生成 1,8-bis(2,4,5-dimethyl-3,6-dioxocyclohexa-1,4-dienyl)-octa-3,5-diyne
  参考文献：
  名称：

  Synthesis, X-Ray Structure Analysis and Topochemical Photopolymerization of 2,5-Dimethoxyphenyl- and Quinone-substituted Octa-3,5-diynes

  摘要：

  The octa-3,5-diynes 3a-g have been synthesized. Subsequent oxidation of 3a-g gave the 1,8-quinone-substituted octa-3,5-diynes 4a-g. The molecular structures of the diynes alpha-3b, beta-3b, 3c, 3e, 3f and 4f have been determined by X-ray diffraction. UV-irradiation of diyne 3e afforded in a single crystal-to-single crystal transformation the highly-ordered polymer 5 under topochemical control. The transformation of 3c into polymer 5 was observed by X-ray diffraction analysis. Irradiation of 4d yielded the first quinone-substituted intensive-blue poly(but-1-en-3-ynylene) 5, which turned red after work up. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00500-7
• 作为产物：
  描述：

  (2,5-dimethoxy-3,4,6-trimethylphenyl)methanol 在 phosphorus tribromide 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 以17.2 g (80.0%)的产率得到1-(溴甲基)-2,5-二甲氧基-3,4,6-三甲基苯
  参考文献：
  名称：

  Certain benzoquinones, naphthoquinones, corresponding hydroquinones

  摘要：

  喹醌衍生物由通式表示##STR1##（其中，R.sup.1和R.sup.2，相同或不同，指氢原子，甲基或甲氧基甲基基团，或R.sup.1和R.sup.2结合在一起形成--CH.dbd.CH--CH.dbd.CH--; R.sup.3是氢原子或甲基; R.sup.4是氮含杂环基团，可能被取代; R.sup.5是氢原子，甲基，可能被取代的羟甲基基团，或者酯化或酰胺化的羧基; Z是##STR2##（其中，R'是氢原子或甲基）; n是0到12之间的整数，m是0到3之间的整数，k是0到7之间的整数，假设当m为2或3时，Z和k能够适当变化在[ ]中显示的重复单元中），以及其对氢醌衍生物，是新颖的化合物，具有改善多不饱和脂肪酸代谢的效果，特别是抑制脂肪酸过氧化物的产生，抑制5-脂氧合酶途径代谢产物的产生，抑制血栓素A.sub.2合成酶，血栓素A.sub.2受体拮抗作用和活性氧物质的清除作用，以及作为药物的用途，如抗血栓药、抗血管收缩剂、抗哮喘药、抗过敏药、治疗银屑病、改善心脏、脑和心血管系统的药物、治疗肾炎、活性氧清除剂、抗癌药、改善阿拉基酸级联产物控制的药物等。

  公开号：

  US04851413A1

文献信息

• Condensed heterocyclic compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05834463A1

  公开（公告）日：1998-11-10

  Compounds represented by the formula: ##STR1## wherein ring A is benzene; Ar is aromatic group; R.sup.1, R.sup.2 and R.sup.3 each stands for H, acyl, hydrocarbon or heterocyclic, or R.sup.2 and R.sup.3, taken together, may form non-aromatic cyclic hydrocarbon; X is methylene or carbonyl; ......... is single bond or double bond; when ......... is single bond, Y is --NR.sup.4 -- (R.sup.4 is H, acyl, hydrocarbon or heterocyclic), when ......... is double bond, Y is N; n is 1-3, provided that, X is carbonyl and, at the same time, R.sup.2 and R.sup.3, taken together, form non-aromatic cyclic hydrocarbon, ......... is double bond or R.sup.4 is a heterocyclic or --Z(CH.sub.2).sub.m --W (Z is methylene or carbonyl, W is optionally substituted amino, and m denotes 0-5), or salts thereof have an excellent GnRH receptor antagonistic action and/or an action of improving sleep disturbances.

  该公式代表的化合物为：##STR1## 其中环A为苯；Ar为芳香族基团；R.sup.1、R.sup.2和R.sup.3分别代表H、酰基、碳氢化合物或杂环；或R.sup.2和R.sup.3一起形成非芳香族环烃；X为亚甲基或羰基；.........为单键或双键；当.........为单键时，Y为--NR.sup.4--（R.sup.4为H、酰基、碳氢化合物或杂环）；当.........为双键时，Y为N；n为1-3，前提是，X为羰基且同时R.sup.2和R.sup.3一起形成非芳香族环烃，.........为双键或R.sup.4为杂环或--Z(CH.sub.2).sub.m--W（Z为亚甲基或羰基，W为可选择取代的氨基，m表示0-5），或其盐具有出色的GnRH受体拮抗作用和/或改善睡眠障碍的作用。
• Certain benzoquinones, naphthoquinones, corresponding hydroquinones
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04851413A1

  公开（公告）日：1989-07-25

  Quinone derivatives represented by the general formula ##STR1## (wherein, R.sup.1 and R.sup.2, the same or different, refer to a hydrogen atom, methyl or methoxymethyl group, or R.sup.1 and R.sup.2 bind together to form --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or methyl group; R.sup.4 is a nitrogen-containing heterocyclic group which may be substituted; R.sup.5 is a hydrogen atom, methyl group, hydroxymethyl group which may be substituted, or a carboxyl group which may be esterified or amidated; Z is ##STR2## (wherein, R' is hydrogen atom or methyl group); n is an integer from 0 through 12, m is an integer from 0 through 3, and k is an integer from 0 through 7, providing that, when m is 2 or 3, Z and k are able to vary appropriately in the repeating unit shown in [ ]), and the hydroquinone derivatives thereof, are novel compounds, possess improvement effects of metabolism of polyunsaturated fatty acids, particularly two or more of inhibition of production of fatty acid peroxides, inhibition of production of metabolites in 5-lipoxygenase pathway, inhibition of thromboxane A.sub.2 synthetase, thromboxane A.sub.2 receptor antagonism and scavenging action of active oxygen species, and of use as drugs, such as antithrombotics, anti-vascular constriction agents, anti-asthma agent, antiallergic agents, therapeutics for psoriasis, agents for improvement in heart, brain and cardiovascular systems, therapeutics for nephritis, active oxygen-eliminating agents, anticancer agents, agents for improvement of control of arachidonate cascade products, etc.

  喹醌衍生物由通式表示##STR1##（其中，R.sup.1和R.sup.2，相同或不同，指氢原子，甲基或甲氧基甲基基团，或R.sup.1和R.sup.2结合在一起形成--CH.dbd.CH--CH.dbd.CH--; R.sup.3是氢原子或甲基; R.sup.4是氮含杂环基团，可能被取代; R.sup.5是氢原子，甲基，可能被取代的羟甲基基团，或者酯化或酰胺化的羧基; Z是##STR2##（其中，R'是氢原子或甲基）; n是0到12之间的整数，m是0到3之间的整数，k是0到7之间的整数，假设当m为2或3时，Z和k能够适当变化在[ ]中显示的重复单元中），以及其对氢醌衍生物，是新颖的化合物，具有改善多不饱和脂肪酸代谢的效果，特别是抑制脂肪酸过氧化物的产生，抑制5-脂氧合酶途径代谢产物的产生，抑制血栓素A.sub.2合成酶，血栓素A.sub.2受体拮抗作用和活性氧物质的清除作用，以及作为药物的用途，如抗血栓药、抗血管收缩剂、抗哮喘药、抗过敏药、治疗银屑病、改善心脏、脑和心血管系统的药物、治疗肾炎、活性氧清除剂、抗癌药、改善阿拉基酸级联产物控制的药物等。
• Hydrindacene-Based Acetylenic Macrocycles with Horizontally and Vertically Ordered Functionality Arrays
  作者：Hidetoshi Kawai、Tatsuya Utamura、Erina Motoi、Tomoko Takahashi、Hiroyoshi Sugino、Manabu Tamura、Masakazu Ohkita、Kenshu Fujiwara、Takao Saito、Takashi Tsuji、Takanori Suzuki

  DOI：10.1002/chem.201200716

  日期：2013.4.2

  The macrocyclization of 2,6‐diethynyl hydrindacenes (1) with functional groups at mutually perpendicular positions results in the formation of novel macrocycles which, as a result of the hindered rotation of the hydrindacene units, possess directionally persistent peripheral functionalities. The two hydrindacene units in the dimer macrocycle (2) have been shown to interact electronically through their

  具有相互垂直位置上的官能团的2,6-二乙炔基苯并二氢（1）的大环化导致形成新的大环，这是由于并苯单元的旋转受阻而具有定向持久的外围功能。已显示二聚体大环（2）中的两个并苯单元通过它们各自的丁二炔部分进行电子相互作用，而三聚体大环（3）由于五元苯并五氢环而显示出中等程度的几何柔韧性。另外，这些三聚体大环化合物包含中心腔，该中心腔的尺寸适合于包含各种溶剂分子。这些新的大环化合物可通过引入π-共轭侧基（如苯乙烯基和噻吩基）以及连接各种外围酯基来进一步修饰。
• An ether-linked halogenated phenazine-quinone prodrug model for antibacterial applications
  作者：Robert W. Huigens III、Hongfen Yang、Ke Liu、Young S. Kim、Shouguang Jin

  DOI：10.1039/d1ob01107c

  日期：——

  need for new antibacterial therapies that eradicate pathogenic bacteria through non-conventional mechanisms. Our group has identified a series of halogenated phenazine (HP) agents that induce rapid iron starvation that leads to potent killing of methicillin-resistant Staphylococcus aureus biofilms. Here, we report the design, chemical synthesis and microbiological assessment of a HP-quinone ether prodrug

  抗生素耐药性感染给患者带来了巨大的挑战。因此，非常需要通过非常规机制根除病原菌的新抗菌疗法。我们的小组已经确定了一系列卤代吩嗪 (HP) 试剂，可诱导快速铁饥饿，从而有效杀死耐甲氧西林金黄色葡萄球菌生物膜。在这里，我们报告了 HP-醌醚前药模型的设计、化学合成和微生物学评估，旨在（1）消除一般（脱靶）铁螯合，以及（2）通过醌的生物还原释放活性 HP 剂扳机。在这里，我们证明前药类似物HP-29-Q具有稳定的醚键，能够释放 HP，并对实验室菌株和多重耐药临床分离株具有中等至良好的抗菌活性。
• Certain benzoquinones, naphthoquinones and derivatives thereof which
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04985447A1

  公开（公告）日：1991-01-15

  Quinone derivatives represented by the general formula ##STR1## (wherein, R.sup.1 and R.sup.2, the same or different, refer to hydrogen atom, methyl or methoxymethyl group, or R.sup.1 and R.sup.2 bind together to form --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is hydrogen atom or methyl group; R.sup.4 is nitrogen-containing heterocyclic group which may be substituted; R.sup.5 is hydrogen atom, methyl group, hydroxymethyl group which may be substituted, or carboxyl group which may be esterified or amidated; Z is ##STR2## --CH.dbd.CH--, ##STR3## or ##STR4## (wherein, R' is hydrogen atom or methyl group); n is an integer from 0 through 12, m is an integer from 0 through 3, and k is an integer from 0 through 7, providing that, when m is 2 or 3, Z and k are able to vary appropriately in the repeating unit shown in [ ]), and the hydroquinone derivatives thereof, are novel compounds, possess improvement effects of metabolism of poly unsaturated fatty acids, particularly two or more inhibitition of production of fatty acid peroxides, inhibition of production of metabolites in 5-lipoxygenase pathway, inhibition of thromboxane A.sub.2 synthetase, thromboxane A.sub.2 receptor antagonism and scavenging action of active oxygen species, and of use as drugs, such as antithrombotics, anti-vascular constriction agents, anti-asthma agent, antiallergic agents, therpeutics for psoriasis, agents for improvement in heart, brain and cardiovascular systems, therapeutics for nephritis, active oxygen-eliminating agents, anticancer agents, agents for improvement of control of arachidonate cascade products, etc.

  通式为##STR1##的醌衍生物（其中，R.sup.1和R.sup.2，相同或不同，指氢原子，甲基或甲氧甲基基团，或R.sup.1和R.sup.2结合形成--CH.dbd.CH--CH.dbd.CH--; R.sup.3是氢原子或甲基基团; R.sup.4是可能被取代的含氮杂环基团; R.sup.5是氢原子，甲基基团，可能被取代的羟甲基基团，或可酯化或酰胺化的羧基; Z是##STR2## --CH.dbd.CH--, ##STR3## 或 ##STR4##（其中，R'是氢原子或甲基基团）; n是0到12的整数，m是0到3的整数，k是0到7的整数，但当m为2或3时，Z和k能够在[ ]中所示的重复单位中适当变化），以及其羟醌衍生物，是新颖的化合物，具有改善多不饱和脂肪酸代谢的效果，特别是抑制脂肪酸过氧化物的产生，抑制5-脂氧合酶途径代谢物的产生，抑制血栓素A.sub.2合酶，血栓素A.sub.2受体拮抗作用和活性氧自由基清除作用，并可用作药物，如抗血栓剂，抗血管收缩剂，抗哮喘剂，抗过敏剂，治疗银屑病的药物，改善心脏，脑和心血管系统的药物，治疗肾炎的药物，活性氧清除剂，抗癌剂，改善花生四烯酸级联产物控制的药物等。