(2-溴-5-甲氧基-4-苯基甲氧基苯基)甲醇 | 65341-82-4

• 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: (2-溴-5-甲氧基-4-苯基甲氧基苯基)甲醇
• 英文名称: 4-benzyloxy-2-bromo-5-methoxybenzyl alcohol
• 英文别名: [4-(benzyloxy)-2-bromo-5-methoxyphenyl]methanol；(2-bromo-5-methoxy-4-phenylmethoxyphenyl)methanol
• CAS: 65341-82-4
• 化学式: C₁₅H₁₅BrO₃
• 分子量: 323.186
• InChiKey: QIBAIRHXPRWLHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-溴-5-甲氧基-4-苯基甲氧基苯基)甲醇 在 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 (E)-1-[[4-(5-methoxycarbonyl-2,3-diphenylmethylenedioxy)phenoxy]phenyl]-2-[2-bromo-4-benzyloxy-5-methoxyphenyl]ethene
  参考文献：
  名称：

  Total Syntheses of Plagiochins A and D, Macrocyclic Bis(bibenzyls), by Pd(0) Catalyzed Intramolecular Stille-Kelly Reaction1

  摘要：

  Total syntheses of plagiochins A (1) and D (4), the former of which exhibits a significant neurotrophic activity, have been accomplished. The key 16-membered ring closure in 4 has been achieved directly from the dibromoperrottetin derivative (7) by Pd(0) catalyzed intramolecular Stille-Kelly reaction, whereas 1 has been synthesized from the dibromide (28) via the trimethylstannyl compounds (29) and (30) by Pd(0) catalyzed intramolecular Stille reaction.

  DOI：

  10.3987/com-00-s(i)26
• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯甲醇 在 pyridinium hydrobromide perbromide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以72%的产率得到(2-溴-5-甲氧基-4-苯基甲氧基苯基)甲醇
  参考文献：
  名称：

  供体取代的 2-（2-卤代苯基）乙醛缩醛的简便和区域选择性合成

  摘要：

  描述了从香兰素 (5a) 开始制备供体取代的 (2-溴苯基) - 和 (2-碘苯基) 乙醛缩醛 13c 和 16c 的简便且高产的方法。通过与氯化鏻 11 的 Wittig 反应和随后加入甲醇，O-苄基香草醛的同系化获得苯乙醛缩醛 15c。15c在甲醇中用溴化吡啶鎓过溴化物溴化以从香草醛以65%的产率得到溴缩醛13c。15c 用碘和碘酸碘化生成碘缩醛 16c。

  DOI：

  10.1002/ardp.19953280402

文献信息

• [EN] cGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU CGAS
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017176812A1

  公开（公告）日：2017-10-12

  Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  揭示了一种新型化合物的化学式（I），这些化合物是cGAS拮抗剂，涉及到这些化合物的制备方法、包含这些化合物的药物组合物，以及它们在医学治疗中的应用。
• Simple, Copper(I)-Catalyzed Oxidation of Benzylic/Allylic Alcohols to Carbonyl Compounds: Synthesis of Functionalized Cinnamates in One Pot
  作者：Alavala Gopi Krishna Reddy、Lodi Mahendar、Gedu Satyanarayana

  DOI：10.1080/00397911.2013.879389

  日期：2014.7.18

  environmentally benign [Cu(I)]-catalyzed oxidation of activated (benzylic/allylic) alcohols to the corresponding carbonyl compounds is presented. Interestingly, the reaction was also compatible with benzylic alcohols containing ortho-bromo substituents on the aromatic ring without competing with the expected intermolecular Buchwald coupling. Significantly, the catalytic system enables the synthesis of cinnamate-esters

  摘要 提出了一种环境友好的 [Cu(I)] 催化将活化的（苄基/烯丙基）醇氧化成相应的羰基化合物。有趣的是，该反应还与芳环上含有邻溴取代基的苯甲醇相容，而不会与预期的分子间 Buchwald 偶联竞争。值得注意的是，该催化系统能够通过氧化和 Wittig-Horner 协议以顺序多米诺一锅法合成肉桂酸酯。图形概要
• An efficient sequential one-pot base mediated C–O and Pd-mediated C–C bond formation: synthesis of functionalized cinnamates and isochromenes
  作者：A. Gopi Krishna Reddy、J. Krishna、G. Satyanarayana

  DOI：10.1016/j.tetlet.2012.08.023

  日期：2012.10

  An efficient sequential one-pot intermolecular oxy-Michael addition and intermolecular Heck coupling for the synthesis of functionalized cinnamates is presented. Bulky tert-butyl acrylate was identified as a more suitable Michael acceptor for initial oxy-Michael addition, as it precludes the formation of undesired cross condensed ester. Most importantly, the present method was further divergently extended

  提出了一种有效的顺序单锅分子间氧-迈克尔加成反应和分子间Heck偶联反应，用于功能化肉桂酸酯的合成。粗大的丙烯酸叔丁酯被认为是更适合的初始氧-迈克尔加成反应的迈克尔受体，因为它阻止了不希望的交叉缩合酯的形成。最重要的是，本发明的方法进一步扩展到通过顺序一锅法O-烯丙基化和随后的分子内Heck环化成功合成异色酮。
• An efficient synthesis of 4-isochromanones via Parham-type cyclization with Weinreb amide
  作者：Chaolei Wang、Zheng Wu、Jia Wang、Jie Liu、Hequan Yao、Aijun Lin、Jinyi Xu

  DOI：10.1016/j.tet.2015.08.028

  日期：2015.10

  The synthesis of 4-isochromanones via Parham-type cyclization with Weinreb amide as the internal electrophilic group, t-BuLi as the lithium reagent was described. The reaction was efficient and could be completed in one minute. The application scope of this new protocol was investigated and the desired products could be obtained in good to excellent yields. Besides, the synthetic potential of this

  4-异色满酮类经由帕海姆型环化的Weinreb合成酰胺作为内部电子基团，吨正丁基锂作为被描述的锂试剂。该反应是有效的，并且可以在一分钟内完成。这个新的协议的应用范围进行了研究和所需产物可以以良好地获得优异的产率。此外，该方法的合成潜力还通过天然产物（±）-XJP的合成得到了进一步证明，该合成是通过六个步骤获得的，总收率高达54％。
• Identification of a Hydrogen-Sulfide-Releasing Isochroman-4-One Hybrid as a Cardioprotective Candidate for the Treatment of Cardiac Hypertrophy
  作者：Yu Wang、Yuechen Liu、Hongyu Wu、Shengtao Xu、Fenfen Ma

  DOI：10.3390/molecules27134114

  日期：——

  Cardiac pathological hypertrophy is associated with undesirable epigenetic changes and causes maladaptive cardiac remodeling and heart failure, leading to high mortality rates. Specific drugs for the treatment of cardiac hypertrophy are still in urgent need. In the present study, a hydrogen-sulfide-releasing hybrid 13-E was designed and synthesized by appending p-hydroxythiobenzamide (TBZ), an H2S-releasing donor, to an analog of our previously discovered cardioprotective natural product XJP, 7,8-dihydroxy-3-methyl-isochromanone-4. This hybrid 13-E exhibited excellent H2S-generating ability and low cellular toxicity. The 13-E protected against cardiomyocyte hypertrophy In Vitro and reduced the induction of Anp and Bnp. More importantly, 13-E could reduce TAC-induced cardiac hypertrophy In Vivo, alleviate cardiac interstitial fibrosis and restore cardiac function. Unbiased transcriptomic analysis showed that 13-E regulated the AMPK signaling pathway and influenced fatty acid metabolic processes, which may be attributed to its cardioprotective activities.

  心肌病理性肥厚与不良的表观遗传学变化有关，会引起不良的心脏重塑和心力衰竭，导致高死亡率。治疗心肌肥厚的特效药物仍亟待开发。在本研究中，通过将对羟基硫代苯甲酰胺（TBZ）（一种 H2S 释放供体）添加到我们之前发现的具有心脏保护作用的天然产物 XJP 的类似物 7,8-二羟基-3-甲基异色满酮-4 中，设计并合成了一种硫化氢释放杂交 13-E。这种杂交 13-E 具有出色的 H2S 生成能力和较低的细胞毒性。13-E 对体外心肌细胞肥大有保护作用，并能减少 Anp 和 Bnp 的诱导。更重要的是，13-E 能减轻 TAC 诱导的体内心脏肥大，减轻心脏间质纤维化并恢复心脏功能。无偏见的转录组分析表明，13-E 可调节 AMPK 信号通路并影响脂肪酸代谢过程，这可能是其具有心脏保护活性的原因。