4-n-hexyloxy-4'-biphenylboronic acid | 158937-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-n-hexyloxy-4'-biphenylboronic acid
• 英文别名: 4'-hexyloxy-biphenyl-4-boronic acid；(4'-(Hexyloxy)-[1,1'-biphenyl]-4-yl)boronic acid；[4-(4-hexoxyphenyl)phenyl]boronic acid
• CAS: 158937-26-9
• 化学式: C₁₈H₂₃BO₃
• 分子量: 298.19
• InChiKey: QYZCPFHQEAZBQN-UHFFFAOYSA-N

物化性质

• 沸点：
  470.9±55.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4-n-hexyloxy-4'-biphenylboronic acid 在 十六烷基三甲基溴化铵 、 palladium diacetate 、 sodium carbonate 、 三苯基膦 、 potassium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 水 、 异丙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 4''-hexyloxy-[1,1':4',1'']terphenyl-4-carboxylic acid
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of caspofungin-like macrocyclic antifungal lipopeptides

  摘要：

  The echinocandins represent a well-known class of macrocyclic antifungal lipopeptides that can be used for treatment of invasive fungal infections. Due to their complex chemical structures and synthetic difficulties, the structure activity relationships (SARs) of them are still limited. A total synthetic approach was developed to synthesize structurally diverse caspofungin-like antifungal cyclic lipopeptides, allowing for systemically investigating their SARs. Most of the designed cyclic lipopeptides showed potent antifungal activities with broad spectrum. In particular, several compounds (e.g., 30a, 30e-h, 31a-d, 32c, and 33a,b) were more active in vitro against Candida albicans or Aspergillus fumigatus than caspofungin. The findings in this work indicated that the 'left' tripeptide segment of cyclic lipopeptide scaffold might be suitable for a hydrophilic structural motif, whereas the 'right' lipotripeptide segment was preferred as a hydrophobic core. The alkoxy-naphthoyl was found to be optimal side chain and alkyl length could affect the SARs of alkoxy-aroyl side chains. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.015
• 作为产物：
  描述：

  4-乙酰氧基联苯 在 sodium hydroxide 、 正丁基锂 、 溴 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 4-n-hexyloxy-4'-biphenylboronic acid
  参考文献：
  名称：

  The Synthesis and Property of Liquid Crystalline 4-Alkoxyl-4″-Cyano-p-Terphenyls

  摘要：

  The synthesis of some new 4-alkoxyl-4 "-cyano-p-terphenyls is described. The preliminary characterization by means of polarized optical microscopy, differential scanning calorimetry and X-ray diffraction shows that all these compounds are thermotropically liquid-crystalline and can form both the nematic and smectic mesophases.

  DOI：

  10.1080/10587250008031039

文献信息

• Donor-Acceptor-Substituted Oligo(1,4-phenylene)s
  作者：Soungkyoo Kim、Annette Oehlhof、Bernhard Beile、Herbert Meier

  DOI：10.1002/hlca.200800398

  日期：2009.6

  Abstractmagnified imageOligo(para‐phenylene)s (DAOPPs) 2a–2d (n=1–4) with terminal donor–acceptor substitution (D=C6H13O, A=NO2) were prepared by applying Suzuki cross‐couplings for chain extension and end capping. The push–pull effect induces short‐reaching polarizations of the chain consisting of conjugated but twisted benzene rings, which was studied by NMR measurements. Electron excitation from the ground‐state S0 to the more planar first‐excited singlet state S1 is combined with a strong intramolecular charge transfer (ICT), which is documented by the red shift of the long‐wavelength absorption (charge‐transfer band) for short chains (one or two repeat units, n = 1 or 2). The opposite influence of decreasing ICT and increasing conjugation length leads to a bathochromic series (λmax(n+1)≥λmax(n)) with a fast saturation of λmax (n). The effective conjugation length nECL=4 corresponds to λ∞ 349 nm. These results are discussed in the context of other oligo(para‐phenylene)s (OPPs).