4-n-nonylbenzeneboronic acid pinacolate | 1356840-19-1

• 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-nonylbenzeneboronic acid pinacolate
• 英文别名: pinacol(4-nonylphenyl)boronate；4,4,5,5-tetramethyl-2-(4-nonylphenyl)-1,3,2-dioxaborolane
• CAS: 1356840-19-1
• 化学式: C₂₁H₃₅BO₂
• 分子量: 330.319
• InChiKey: CGTVDWIISBXJEB-UHFFFAOYSA-N

物化性质

• 沸点：
  419.1±24.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-n-nonylbenzeneboronic acid pinacolate 在 potassium hydrogen fluoride 、 三甲基氯硅烷 、 水 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 4-壬基苯硼酸
  参考文献：
  名称：

  Design and synthesis of boronic acid inhibitors of endothelial lipase

  摘要：

  Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.043
• 作为产物：
  描述：

  4-硝基苯酚三氟甲基磺酸酯 在 2-双环己基膦-2',6'-二甲氧基联苯 、 盐酸 、 potassium phosphate monohydrate 、 palladium on activated charcoal 、 氢气 、 palladium diacetate 、 三乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 生成 4-n-nonylbenzeneboronic acid pinacolate
  参考文献：
  名称：

  Design and synthesis of boronic acid inhibitors of endothelial lipase

  摘要：

  Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.043

文献信息

• Stabilised columnar mesophases formed by 1 : 1 mixtures of hexaalkoxytriphenylenes with a hexaphenyltriphenylene-based polymer
  作者：Sholto R. McLaren、Daniel J. Tate、Owen R. Lozman、Georg H. Mehl、Richard J. Bushby

  DOI：10.1039/c5tc00661a

  日期：——

  The synthesis is reported for a main chain polymer in which the repeat units are 2,3,6,7,10,11-hexaphenyltriphenylene moieties linked through flexible dodecyl chains.

  合成报告了一种主链聚合物，其中重复单元是通过柔性十二烷基链连接的2,3,6,7,10,11-六苯基三苯基单元。
• Efficient Bottom‐Up Preparation of Graphene Nanoribbons by Mild Suzuki–Miyaura Polymerization of Simple Triaryl Monomers
  作者：Gang Li、Ki‐Young Yoon、Xinjue Zhong、Xiaoyang Zhu、Guangbin Dong

  DOI：10.1002/chem.201602007

  日期：2016.6.27

  efficient bottom‐up solution‐phase synthesis of N=9 armchair graphene nanoribbons (GNRs) is described. Catalyzed by Pd(PtBu3)2, Suzuki–Miyaura polymerization of a simple and readily available triaryl monomer provides a novel GNR precursor with a high molecular weight and excellent solubility. Upon cyclodehydrogenation, the resulting GNR exhibits semiconducting properties with an approximately 1.1 eV band

  本文描述了N = 9扶手椅石墨烯纳米带（GNR）的有效的自下而上的解决方案阶段合成。在Pd（P t Bu 3）2的催化下，简单易得的三芳基单体的Suzuki-Miyaura聚合反应提供了一种新型的GNR前体，具有高分子量和出色的溶解性。进行环脱氢后，所得到的GNR表现出半导体性质，其带隙约为1.1 eV（LUMO：-3.52 eV； HOMO：-4.66 eV），通过紫外/可见-近红外光谱和循环伏安法表征。
• Design and synthesis of boronic acid inhibitors of endothelial lipase
  作者：Daniel P. O’Connell、Daniel F. LeBlanc、Debra Cromley、Jeffrey Billheimer、Daniel J. Rader、William W. Bachovchin

  DOI：10.1016/j.bmcl.2011.12.043

  日期：2012.2

  Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL. (C) 2011 Elsevier Ltd. All rights reserved.