3-hexyloxyphenylboronic acid | 442686-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-hexyloxyphenylboronic acid
• 英文别名: m-hexyloxyphenylboronic acid；[3-(Hexyloxy)phenyl]boronic acid；(3-hexoxyphenyl)boronic acid
• CAS: 442686-90-0
• 化学式: C₁₂H₁₉BO₃
• 分子量: 222.092
• InChiKey: LHUPSBMTJZBMES-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C(Solv: ligroine (8032-32-4))
• 沸点：
  376.5±44.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-hexyloxyphenylboronic acid 在 tris(dibenzylideneacetone)dipalladium (0) 、 palladium dichloride 吡啶 、 1,1'-双(二苯基膦)二茂铁 、 三氯化铁 、 sodium carbonate 、 三苯基膦 、 二苯基膦酸锂 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 50.0h， 生成 6,11-Bis-hexyloxy-triphenylene-2,3-dicarbonitrile
  参考文献：
  名称：

  Macrodiscotic triphenylenophthalocyanines

  摘要：

  首次合成了具有高度取代基的三蝶烯酞菁，并发现它们具有介晶性。

  DOI：

  10.1039/b200978a
• 作为产物：
  描述：

  间溴苯酚 在 potassium carbonate 、 magnesium 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 3-hexyloxyphenylboronic acid
  参考文献：
  名称：

  摘要：

  A series of novel triphenylenes has been synthesised by a combination of palladium catalysed coupling, oxidative cyclisation, bromination and nucleophilic aromatic substitution. The new derivatives are designed to have structures which are intermediate between the known symmetrical materials hexakis( hexyloxy) triphenylene and hexakis( hexylthio) triphenylene. The compounds having four hexyloxy and two hexylthio substituents form only Col(h) mesophases. Triphenylenes having four hexylthio and two hexyloxy substituents also give Col(h) mesophases but 3,6- bis(hexyloxy)-2,7,10,11-tetrakis(hexylthio) triphenylene 5 is unique in that it cools into a stable, more ordered phase. The low temperature phase, which appears to be indefinitely stable at ambient temperature, is assumed to be helical based on transition enthalpy data.

  DOI：

  10.1039/b103450m

文献信息

• Probing the structural factors influencing columnar mesophase formation and stability in triphenylene discotics
  作者：Andrew N. Cammidge、Céline Chausson、Hemant Gopee、Juanjuan Li、David L. Hughes

  DOI：10.1039/b913678a

  日期：——

  Series of structurally related substituted triphenylene derivatives were designed and synthesised to interrogate key features which determine mesophase formation and stability, and to challenge the general conclusions previously proposed by us and others. It is apparent that no single, simple principle can be universally applied.

  设计并合成了一系列结构相关的替代三苯基衍生物，以探讨决定介相形成和稳定性的关键特征，并挑战我们和其他人之前提出的一般结论。显然，没有单一的简单原则可以普遍适用。
• Synthesis of masked haloareneboronic acids via iridium-catalyzed aromatic C–H borylation with 1,8-naphthalenediaminatoborane (danBH)
  作者：Noriyuki Iwadate、Michinori Suginome

  DOI：10.1016/j.jorganchem.2008.11.068

  日期：2009.5

  "Masked" areneboronic acids have been prepared by Ir-catalyzed C-H borylation of arenes. A [Ir(OMe)(cod)](2) complex with a DPPE ligand showed the highest catalytic activity in the C-H borylation of benzene at 80 degrees C. The reaction system can be applied to substituted arenes, including halogen-substituted arenes. 1,3-Dihalobenzenes undergo the C-H borylation at their 5-positions in a regioselective fashion, affording 3,5-dihaloareneboronic acid derivatives, which serve as useful coupling modules for the convergent dendrimer synthesis. (C) 2008 Elsevier B.V. All rights reserved.

  通过铱 (Ir)-催化的 C-H 键硼化反应，已成功制备了“屏蔽”的芳香族硼酸。含有 DPPE 配体的 [Ir(OMe)(cod)](2) 复合物在 80°C 下对苯的 C-H 键硼化反应表现出最高的催化活性。该反应体系可应用于取代芳香族物质，包括卤素取代的芳香族化合物。1,3-二卤苯在区域选择性条件下于其 5 位发生 C-H 键硼化反应，生成 3,5-二卤芳香族硼酸衍生物，这些衍生物可作为有用的偶联模块，用于收敛型树状大分子的合成。© 2008 Elsevier B.V. 保留所有权利。
• Mixed Alkyl-Alkoxy Triphenylenes
  作者：Andrew N Cammidge、Hemant Gopee

  DOI：10.1080/714965603

  日期：2003.1
• Macrodiscotic triphenylenophthalocyanines
  作者：Andrew N. Cammidge、Hemant Gopee

  DOI：10.1039/b200978a

  日期：2002.4.19

  The first heavily substituted triphenylenophthalocyanines have been synthesised and found to be mesogenic.

  首次合成了具有高度取代基的三蝶烯酞菁，并发现它们具有介晶性。
• ——
  作者：Andrew N Cammidge、Hemant Gopee

  DOI：10.1039/b103450m

  日期：2001.10.23

  A series of novel triphenylenes has been synthesised by a combination of palladium catalysed coupling, oxidative cyclisation, bromination and nucleophilic aromatic substitution. The new derivatives are designed to have structures which are intermediate between the known symmetrical materials hexakis( hexyloxy) triphenylene and hexakis( hexylthio) triphenylene. The compounds having four hexyloxy and two hexylthio substituents form only Col(h) mesophases. Triphenylenes having four hexylthio and two hexyloxy substituents also give Col(h) mesophases but 3,6- bis(hexyloxy)-2,7,10,11-tetrakis(hexylthio) triphenylene 5 is unique in that it cools into a stable, more ordered phase. The low temperature phase, which appears to be indefinitely stable at ambient temperature, is assumed to be helical based on transition enthalpy data.