4-(2,2-dibromovinyl)-2-methoxyphenol | 218903-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2,2-dibromovinyl)-2-methoxyphenol
• 英文别名: 4-(2,2-Dibromoethenyl)-2-methoxyphenol
• CAS: 218903-31-2
• 化学式: C₉H₈Br₂O₂
• 分子量: 307.969
• InChiKey: HHISGHZDYJIJBH-UHFFFAOYSA-N

物化性质

• 沸点：
  345.9±37.0 °C(Predicted)
• 密度：
  1.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  4-(2,2-dibromovinyl)-2-methoxyphenol 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 氢气 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 4-[2-[5-[2-(4-hydroxy-3-methoxyphenyl)ethyl]pyridin-3-yl]ethyl]-2-methoxyphenol
  参考文献：
  名称：

  Synthesis of symmetrical bis-alkynyl or alkyl pyridine and thiophene derivatives and their antiangiogenic activities

  摘要：

  Fourteen symmetrical bis-alkynyl pyridine and thiophene derivatives were synthesized and their antiangiogenic activity was evaluated with the proliferation and tube formation inhibitory activity on the human umbilical vein endothelial cells (HUVEC). Compounds 6, 8, and 10, rigid mimetic structure of curcumin, showed the potent growth inhibitory activity and the potent tube formation inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.065
• 作为产物：
  描述：

  β,β-dibromo-4-isopropoxy-3-methoxystyrene 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到4-(2,2-dibromovinyl)-2-methoxyphenol
  参考文献：
  名称：

  Selective Cleavage of Isopropyl Aryl Ethers by Aluminum Trichloride^†

  摘要：

  DOI：

  10.1021/jo9808526

文献信息

• Synthesis and Photoswitching Properties of Bioinspired Dissymmetric γ-Pyrone, an Analogue of Cyclocurcumin
  作者：Jérémy Pecourneau、Raúl Losantos、Antonio Monari、Stéphane Parant、Andreea Pasc、Maxime Mourer

  DOI：10.1021/acs.joc.1c00598

  日期：2021.6.18

  approach could conveniently afford the 2,6-disubstituted-γ-pyrone analogue of CC, in ten steps and with an overall yield of 18%. The photophysical properties of our biomimetic analogue have also been characterized showing an improved photoisomerization yield over the parent natural compound. The potentially improved nonlinear optical properties, as well as enhanced stability, may be correlated to the enforcement

  环姜黄素 (CC) 是一种具有潜在治疗特性的姜黄类姜黄素，也是一种天然光开关，可在紫外光下发生E / Z光异构化。为了在相关生物应用中进一步开发，需要在近红外 (NIR) 照射下进行光活化。这种要求可以通过适当的化学修饰来满足，有利于双光子吸收 (TPA) 概率。在此，描述了 CC 的仿生 2,6-二取代-γ-吡喃酮类似物的通用和有效合成，其动机是分子建模预测其 NIR TPA 与 CC 相比的数量级增加。已经确定了三种逆合成途径 (i)通过芳基-恶唑中间体或通过芳基二炔酮通过 (ii) 自下而上或 (iii) 自上而下的方法。在避免通过不稳定的合成子或低产率中间反应的同时，只有最新的方法才能方便地提供 CC 的 2,6-二取代-γ-吡喃酮类似物，分十步，总产率为 18%。我们的仿生类似物的光物理特性也已被表征，显示出比母体天然化合物更高的光异构化产率。潜在改进的非线性光学特性以及增强的稳定性可能与导致四极
• Conjugation of Hydroxytyrosol with Other Natural Phenolic Fragments: From Waste to Antioxidants and Antitumour Compounds
  作者：Erika Tassano、Angela Alama、Andrea Basso、Giancarlo Dondo、Andrea Galatini、Renata Riva、Luca Banfi

  DOI：10.1002/ejoc.201500931

  日期：2015.10

  Hydroxytyrosol, a natural polyphenol that can be extracted from olive mill waste waters, was converted into a series of more complex and lipophilic analogues by conjugation with other naturally derived (poly)phenolic fragments. Ether and triazole linkers were employed. A small library of compounds was prepared, stressing step economy and operational simplicity. Some of these substances were proven

  羟基酪醇是一种可以从橄榄厂废水中提取的天然多酚，通过与其他天然衍生的（多）酚类片段结合，转化为一系列更复杂和亲脂的类似物。使用醚和三唑接头。准备了一个小型化合物库，强调步骤经济和操作简单。在自由基清除试验以及对肿瘤细胞的细胞毒性试验中，这些物质中的一些被证明具有与母体羟基酪醇相同或优于母体羟基酪醇的活性。
• Rapid Synthesis of Triazole-Modified Resveratrol Analogues via Click Chemistry
  作者：Francesca Pagliai、Tracey Pirali、Erika Del Grosso、Riccardo Di Brisco、Gian Cesare Tron、Giovanni Sorba、Armando A. Genazzani

  DOI：10.1021/jm051118z

  日期：2006.1.1

  Resveratrol is a phytoalexin able to display an array of biological activities. We decided to replace the double bond with a triazole ring using the archetypical click reaction: the Huisgen [3 + 2] cycloaddition. Seventy-two triazole derivatives were synthesized via a parallel combinatorial approach. Preliminary data suggest that this procedure can lead to the synthesis of compounds that display some, but not all, of resveratrol's actions with increased potency.
• Total synthesis of moniliformediquinone and calanquinone A as potent inhibitors for breast cancer
  作者：Shankar Thangaraj、Wen-Shing Tsao、Yi-Wei Luo、Yean-Jang Lee、Chia-Fu Chang、Chun-Cheng Lin、Biing-Jiun Uang、Chia-Chun Yu、Jih-Hwa Guh、Che-Ming Teng

  DOI：10.1016/j.tet.2011.06.054

  日期：2011.8

  The first synthesis of moniliformediquinone has been achieved in which the longest linear sequence is only nine steps. The synthesis proceeds in 23% overall yield from commercially available 2,4,5-trimethoxybenzaldehyde. The key transformations include a Pd-catalyzed coupling between a phenyl triflate and an acetylene, and a TiCl4-mediated cyclization of a benzoquinone intermediate. In addition, in vitro inhibitory effects of moniliformediquinone, denbinobin, moscatilin, and calanquinone A were determined to have IC50 values of 0.7, 1.6, 2.5, and 1.5 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of symmetrical bis-alkynyl or alkyl pyridine and thiophene derivatives and their antiangiogenic activities
  作者：Chan Mug Ahn、Woon-Seob Shin、Ho Bum Woo、Seokjoon Lee、Hyean-Woo Lee

  DOI：10.1016/j.bmcl.2004.05.065

  日期：2004.8

  Fourteen symmetrical bis-alkynyl pyridine and thiophene derivatives were synthesized and their antiangiogenic activity was evaluated with the proliferation and tube formation inhibitory activity on the human umbilical vein endothelial cells (HUVEC). Compounds 6, 8, and 10, rigid mimetic structure of curcumin, showed the potent growth inhibitory activity and the potent tube formation inhibitory activity. (C) 2004 Elsevier Ltd. All rights reserved.