6-(3,5-Dimethoxy-phenyl)-naphthalen-2-ol | 869788-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(3,5-Dimethoxy-phenyl)-naphthalen-2-ol
• 英文别名: 6-(3,5-dimethoxyphenyl)naphthalen-2-ol
• CAS: 869788-92-1
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: HYWKEQNSMAOKKU-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  462.8±35.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  6-(3,5-Dimethoxy-phenyl)-naphthalen-2-ol 在 三溴化硼 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 以55%的产率得到5-(6-Hydroxy-naphthalen-2-yl)-benzene-1,3-diol
  参考文献：
  名称：

  Synthesis of a Resveratrol Analogue with High Ceramide-Mediated Proapoptotic Activity on Human Breast Cancer Cells

  摘要：

  Resveratrol, a natural product with a stilbene structure, exerts profound proapoptotic activity in human cancer cells, by triggering the accumulation of ceramide, a bioactive sphingolipid. We studied the biological effects of seven methoxylated and/or naphthalene-based resveratrol analogues and compared these compounds with resveratrol with the objective to identify an analogue with higher ceramide-mediated proapoptotic activity relative to resveratrol. Here we show that the compound with three hydroxyls and a naphthalene ring is the most effective in triggering apoptosis coupled to the induction of endogenous ceramide in human cancer cells.

  DOI：

  10.1021/jm050528k
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 四(三苯基膦)钯 、 正丁基锂 、 四丁基氟化铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 13.0h， 生成 6-(3,5-Dimethoxy-phenyl)-naphthalen-2-ol
  参考文献：
  名称：

  Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells

  摘要：

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.

  DOI：

  10.1021/jm060253o

文献信息

• Chemoselective Cross-Coupling between Two Different and Unactivated C(aryl)–O Bonds Enabled by Chromium Catalysis
  作者：Jinghua Tang、Liu Leo Liu、Shangru Yang、Xuefeng Cong、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/jacs.0c00283

  日期：2020.4.29

  combination of low-cost Cr(II) salt, 4,4-di-tert-butyl-2,2-dipyridyl (dtbpy) ligand and magnesium reductant shows high reactivity in promoting the reductive cross-coupling of aryl methyl ether derivatives with aryl esters, by cleavage and coupling of two different C(aryl)-O bonds under mild conditions. The formation of active low-valent Cr species by reduction of CrCl2 with Mg can be considered, which prefers

  我们在这里报告了两个不同且未活化的 C(芳基)-O 键与铬催化之间交叉耦合的第一个例子。低成本的 Cr(II) 盐、4,4-二叔丁基-2,2-二吡啶基 (dtbpy) 配体和镁还原剂的组合在促进芳基甲基醚衍生物与芳基酯，通过在温和条件下裂解和偶联两个不同的 C(芳基)-O 键。可以考虑通过用 Mg 还原 CrCl2 形成活性低价 Cr 物种，它更喜欢在 dtbpy 和邻亚氨基助剂的螯合帮助下最初激活苯基甲基醚的 C(芳基)-O 键。随后的连续还原、第二次 C(芳基)-O 活化和还原消除允许实现 C(芳基)-O/C(芳基)-O 键的选择性交叉偶联。
• Reductive Cross-Coupling between Unactivated C(aryl)–N and C(aryl)–O Bonds by Chromium Catalysis Using a Bipyridyl Ligand
  作者：Jinghua Tang、Fei Fan、Xuefeng Cong、Lixing Zhao、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/jacs.0c05730

  日期：2020.7.22

  Reductive cross-coupling between two chemically inert bonds remains a great challenge in synthetic chemistry. We report here the reductive cross-coupling between unactivated C(aryl)-N and C(aryl)-O bonds that was achieved by chromium catalysis. The simple and inexpensive CrCl2 salt, combined with important bipyridyl ligand and magnesium reductant, shows high reactivity in the successive cleavage of

  两个化学惰性键之间的还原交叉偶联仍然是合成化学中的一大挑战。我们在这里报告了通过铬催化实现的未活化的 C(芳基)-N 和 C(芳基)-O 键之间的还原交叉耦合。简单且廉价的 CrCl2 盐，结合重要的联吡啶配体和镁还原剂，在苯胺衍生物的 C(芳基)-N 键和芳基酯的 C(芳基)-O 键的连续裂解中显示出高反应性，允许交叉-这两个未活化的不同键以还原方式偶联形成 C(芳基)-C(芳基)键。氘标记实验的机理研究表明，苯胺中的 C(芳基)-N 键优先被活性 Cr 物种裂解，其中联吡啶与 Cr 的连接采用 1 中的配位模型：
• Chromium-Catalyzed Selective Borylation of Vinyl Triflates and Unactivated Aryl Carboxylic Esters with Pinacolborane
  作者：Li Gong、Chao Li、Fangyan Yuan、Senlin Liu、Xiaoming Zeng

  DOI：10.1021/acs.orglett.2c01015

  日期：2022.5.6

  catalysis via the selective formation of vinyl and aryl boronate esters. The competing hydrided reduction or allylic borylation proceeds sluggishly or does not occur, therefore providing a selective strategy for the incorporation of boronate into olefins and arenes. Mechanistic studies indicate that the σ-bond metathesis or oxidative addition mechanism may be considered to be responsible for the cleavage

  使用频哪醇硼烷对丰富的乙烯基三氟甲磺酸酯和未活化的芳基羧酸酯进行硼酸化是通过铬催化选择性形成乙烯基和芳基硼酸酯实现的。竞争性氢化还原或烯丙基硼化反应缓慢或不发生，因此为将硼酸盐结合到烯烃和芳烃中提供了一种选择性策略。机理研究表明，σ键复分解或氧化加成机制可能被认为是酯支架断裂的原因。
• Synthesis of a Resveratrol Analogue with High Ceramide-Mediated Proapoptotic Activity on Human Breast Cancer Cells
  作者：Filippo Minutolo、Giusy Sala、Annalisa Bagnacani、Simone Bertini、Isabella Carboni、Giorgio Placanica、Giovanni Prota、Simona Rapposelli、Nicoletta Sacchi、Marco Macchia、Riccardo Ghidoni

  DOI：10.1021/jm050528k

  日期：2005.11.1

  Resveratrol, a natural product with a stilbene structure, exerts profound proapoptotic activity in human cancer cells, by triggering the accumulation of ceramide, a bioactive sphingolipid. We studied the biological effects of seven methoxylated and/or naphthalene-based resveratrol analogues and compared these compounds with resveratrol with the objective to identify an analogue with higher ceramide-mediated proapoptotic activity relative to resveratrol. Here we show that the compound with three hydroxyls and a naphthalene ring is the most effective in triggering apoptosis coupled to the induction of endogenous ceramide in human cancer cells.
• Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells
  作者：Marinella Roberti、Daniela Pizzirani、Maurizio Recanatini、Daniele Simoni、Stefania Grimaudo、Di Cristina、Vincenzo Abbadessa、Nicola Gebbia、Manlio Tolomeo

  DOI：10.1021/jm060253o

  日期：2006.5.1

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.