(2-(but-3-en-1-yloxy)phenyl)boronic acid | 1334402-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-(but-3-en-1-yloxy)phenyl)boronic acid
• 英文别名: [2-(But-3-en-1-yloxy)phenyl]boronic acid；(2-but-3-enoxyphenyl)boronic acid
• CAS: 1334402-83-3
• 化学式: C₁₀H₁₃BO₃
• mdl: MFCD20290349
• 分子量: 192.022
• InChiKey: MVCOJELFIBMARL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (2-(but-3-en-1-yloxy)phenyl)boronic acid 在 dipotassium peroxodisulfate 、 potassium hydrogen bifluoride 、 silver nitrate 作用下， 以 甲醇 、 水 、 2,3,4-三氟甲苯 为溶剂， 反应 1.08h， 生成 2-(chroman-4-ylmethyl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Practical Radical Cyclizations with Arylboronic Acids and Trifluoroborates

  摘要：

  Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and In a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, Illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.

  DOI：

  10.1021/ol2023505
• 作为产物：
  描述：

  1-溴-2-(丁-3-烯-1-基氧基)苯 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 苯 为溶剂， 反应 1.5h， 以84%的产率得到(2-(but-3-en-1-yloxy)phenyl)boronic acid
  参考文献：
  名称：

  Practical Radical Cyclizations with Arylboronic Acids and Trifluoroborates

  摘要：

  Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and In a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, Illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.

  DOI：

  10.1021/ol2023505

文献信息

• New 5-Aryl-1<i>H</i>-imidazoles Display in Vitro Antitumor Activity against Apoptosis-Resistant Cancer Models, Including Melanomas, through Mitochondrial Targeting
  作者：Véronique Mathieu、Emilie Van Den Berge、Justine Ceusters、Tomasz Konopka、Antonin Cops、Céline Bruyère、Christine Pirker、Walter Berger、Tran Trieu-Van、Didier Serteyn、Robert Kiss、Raphaël Robiette

  DOI：10.1021/jm400287v

  日期：2013.9.12

  We designed and synthesized 48 aryl-1H-imidazole derivatives and investigated their in vitro growth inhibitory activity in cancer cell lines known to present various levels of resistance to proapoptotic stimuli. The IC50 in vitro growth inhibitory concentration of these compounds ranged from >100 mu M to single digit mu M. Among the most active compounds, 2i displayed similar in vitro growth inhibition in cancer cells independent of the cells' levels of resistance to proapoptotic stimuli and was found to be cytostatic in melanoma cell lines. Compound 2i was then tested by the National Cancer Institute Human Tumor Cell Line Anti-Cancer Drug Screen, and the NCI COMPARE algorithm did not reveal any correlation between its growth inhibition profiles with the NCI database compound profiles. The use of transcriptomically characterized melanoma models then enabled us to highlight mitochondrial targeting by 2i. This hypothesis was further confirmed by reactive oxygen production measurement and oxygen consumption analysis.
• Practical Radical Cyclizations with Arylboronic Acids and Trifluoroborates
  作者：Jonathan W. Lockner、Darryl D. Dixon、Rune Risgaard、Phil S. Baran

  DOI：10.1021/ol2023505

  日期：2011.10.21

  Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and In a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, Illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.