1-壬基硼酸 | 3088-78-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 1-壬基硼酸
• 英文名称: dihydroxy-nonyl-borane
• 英文别名: Dihydroxy-nonyl-boran；Nonylboronsaeure；nonyl-boronic acid；Nonylboronic acid
• CAS: 3088-78-6
• 化学式: C₉H₂₁BO₂
• 分子量: 172.076
• InChiKey: RHPOAOZKVCLNPE-UHFFFAOYSA-N

物化性质

• 沸点：
  280.1±23.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  1-壬基硼酸 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 4,4,5,5-tetramethyl-2-(3-nonylphenyl)-1,3,2-dioxaborolane
  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

• Modular Synthesis of Polysubstituted Quinolin-3-amines by Oxidative Cyclization of 2-(2-Isocyanophenyl)acetonitriles with Organoboron Reagents
  作者：Shihui Wang、Jian Xu、Qiuling Song

  DOI：10.1021/acs.orglett.1c02373

  日期：2021.9.3

  quinolin-3-amines. 2-(2-Isocyanophenyl)acetonitriles and organoboron reagents are suitable substrates for this reaction. The remarkable advantages of this protocol are the practical method, mild approach, high reaction efficiency, and good compatibility of functional groups, providing straightforward access to functional quinoline derivatives.

  多取代的 quinolin-3-amines 是重要的结构基序，因为它们具有广泛的生物活性和多功能的转化能力。但是，它们不容易访问。我们公开了一种使用 Mn(III) 乙酸盐作为温和的单电子氧化剂的协议，促进了构建多取代喹啉-3-胺的自由基过程。2-(2-异氰基苯基)乙腈和有机硼试剂是该反应的合适底物。该协议的显着优点是方法实用、方法温和、反应效率高、官能团兼容性好，为获得功能性喹啉衍生物提供了直接途径。
• Visible light as a sole requirement for alkylation of α-C(sp³)–H of <i>N</i>-aryltetrahydroisoquinolines with alkylboronic acids
  作者：Feihu Cong、Wenjing Zhang、Gan Zhang、Jie Liu、Yicheng Zhang、Chao Zhou、Lei Wang

  DOI：10.1039/d3ob01154b

  日期：——

  developed under visible-light irradiation in the absence of additional photocatalyst. The reaction proceeded well, tolerating a variety of functional groups, and featured low-cost and mild reaction conditions. A preliminary mechanistic study indicated that an electron donor–acceptor (EDA) complex between an electron-rich N-aryltetrahydroisoquinoline and an electron-poor alkylboronic acid was involved

  在没有额外光催化剂的情况下，在可见光照射下，用烷基硼酸对N-芳基四氢异喹啉进行α-C(sp 3 )–H的烷基化。反应进行良好，可耐受多种官能团，且成本低、反应条件温和。初步的机理研究表明，富电子的N-芳基四氢异喹啉和缺电子的烷基硼酸之间的电子供体-受体（EDA）络合物参与了该反应。
• 10.1021/acs.orglett.4c02154
  作者：Xin, Hong、Zhang, Lu、Liao, Jinyi、Duan, Xin-Hua、Yang, Xu、Guo, Li-Na

  DOI：10.1021/acs.orglett.4c02154

  日期：——

  A photoredox-catalyzed sequential decarboxylative/defluorinative aminoalkylation of CF3-alkenes with N-arylglycines is described. This metal-free and redox-neutral protocol provided efficient access to the monofluoroalkenyl-1,5-diamines in good yields with excellent functional group compatibility. Mechanistic studies revealed that the reaction proceeds via a radical pathway with the gem-difluoroalkenyl

  描述了CF 3 -烯烃与N-芳基甘氨酸的光氧化还原催化顺序脱羧/脱氟氨基烷基化。这种无金属且氧化还原中性的方案能够以良好的产率有效地获得单氟烯基-1,5-二胺，并具有出色的官能团相容性。机理研究表明该反应以偕二氟烯基胺为中间体通过自由基途径进行。
• 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.

表征谱图