4-(1-羟基乙基)苯硼酸 | 518336-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(1-羟基乙基)苯硼酸
• 中文别名: 4-(1-羟乙基)苯基硼酸
• 英文名称: (4-(1-hydroxyethyl)phenyl)boronic acid
• 英文别名: 4-(1-hydroxyethyl)phenylboronic acid；[4-(1-hydroxyethyl)phenyl]boronic acid
• CAS: 518336-20-4
• 化学式: C₈H₁₁BO₃
• 分子量: 165.985
• InChiKey: QORATNLZEOZUPG-UHFFFAOYSA-N

物化性质

• 沸点：
  350.8±44.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-(1-羟基乙基)苯硼酸 在 potassium hydrogen bifluoride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 potassium 4-(1-hydroxyethyl)phenyltrifluoroborate
  参考文献：
  名称：

  Oxidation of Hydroxyl-Substituted Organotrifluoroborates

  摘要：

  Potassium- and tetra-n-butylammonium organotrifluoroborates containing hydroxyl groups have been prepared and oxidized using several common oxidants. Aryl-, alkenyl-, and alkyltrifluoroborates containing both primary and secondary hydroxyl groups were oxidized in moderate to excellent yields with complete retention of the trifluoroborate moiety. The utility of these oxidized products was demonstrated in a Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1021/ja062974i
• 作为产物：
  描述：

  4-乙酰基苯硼酸 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以93%的产率得到4-(1-羟基乙基)苯硼酸
  参考文献：
  名称：

  脂肪酶催化的含硼手性醇的高对映选择性动力学拆分

  摘要：

  描述了酶作为催化剂首次获得光学纯硼化合物的应用。研究了含硼手性醇通过脂肪酶催化的对映选择性酯交换反应的动力学拆分。含有硼酸酯或硼酸基团的芳族，烯丙基和脂族仲醇可通过南极假丝酵母（CALB）的脂肪酶分解，并具有出色的E值（E > 200）和高对映体过量（最高> 99％）获得底物和乙酰化产物。

  DOI：

  10.1021/ol901091f

文献信息

• [EN] HETEROARYL COMPOUNDS AND THEIR USE AS THERAPEUTIC DRUGS<br/>[FR] COMPOSÉS HÉTÉROARYLE ET LEUR UTILISATION COMME MÉDICAMENTS THÉRAPEUTIQUES
  申请人：DONG-A SOCIO HOLDINGS CO LTD

  公开号：WO2017039331A1

  公开（公告）日：2017-03-09

  The present invention provides heterocyclic compounds, the stereoisomer thereof, the enantiomer thereof, or the pharmaceutically acceptable salt, which are capable of modulating the activity of Mer receptor tyrosine kinase (MERTK). This invention also provides pharmaceutical compositions thereof, methods to prepare the said compounds, and the use of such compounds as a medicament. The present invention is directed to MERTK inhibitory compounds with marked potency, thereby having an outstanding potential for a pharmaceutical intervention of cancer and any other diseases related to MERTK dysregulation.

  本发明提供了一种杂环化合物、其立体异构体、对映异构体或药用可接受的盐，这些化合物能够调节Mer受体酪氨酸激酶（MERTK）的活性。本发明还提供了这些化合物的药物组合物、制备所述化合物的方法以及将这些化合物用作药物的应用。本发明针对的是具有显著活性的MERTK抑制性化合物，因此具有在癌症和任何与MERTK调控失调相关的疾病中进行药物干预的卓越潜力。
• Lipase-Catalyzed Highly Enantioselective Kinetic Resolution of Boron-Containing Chiral Alcohols
  作者：Leandro H. Andrade、Thiago Barcellos

  DOI：10.1021/ol901091f

  日期：2009.7.16

  to obtain optically pure boron compounds is described. The kinetic resolution of boron-containing chiral alcohols via enantioselective transesterification catalyzed by lipases was studied. Aromatic, allylic, and aliphatic secondary alcohols containing a boronate ester or boronic acid group were resolved by lipase from Candida antartica (CALB), and excellent E values (E > 200) and high enantiomeric excesses

  描述了酶作为催化剂首次获得光学纯硼化合物的应用。研究了含硼手性醇通过脂肪酶催化的对映选择性酯交换反应的动力学拆分。含有硼酸酯或硼酸基团的芳族，烯丙基和脂族仲醇可通过南极假丝酵母（CALB）的脂肪酶分解，并具有出色的E值（E > 200）和高对映体过量（最高> 99％）获得底物和乙酰化产物。
• Widely Exploited, Yet Unreported: Regiocontrolled Synthesis and the Suzuki-Miyaura Reactions of Bromooxazole Building Blocks
  作者：Vitalii V. Solomin、Dmytro S. Radchenko、Evgeniy Y. Slobodyanyuk、Oleksandr V. Geraschenko、Bohdan V. Vashchenko、Oleksandr O. Grygorenko

  DOI：10.1002/ejoc.201900032

  日期：2019.5.15

  An approach to synthesis of all isomeric bromooxazoles was optimized and its scope was extended to all three isomeric parents, as well as various alkyl‐ and aryl‐substituted bromooxazoles. The direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common and led exclusively to the target substituted 2‐, 4‐, and 5‐bromooxazoles on multigram scale. The utility of

  优化了所有异构体溴恶唑的合成方法，并将其范围扩展到所有三个异构体母体，以及各种烷基和芳基取代的溴恶唑。直接区位控制的锂化反应，随后与亲电溴源反应是很常见的现象，并且仅在毫克数范围内导致目标取代的2-，4-和5-溴恶唑。在平行合成条件下，Suzuki-Miyaura交叉偶联反应证明了在这项工作中获得的多功能构建基块的效用。
• Eco-friendly iron-catalyzed oxidation of unstrained tertiary aromatic alcohols to ketones
  作者：Shanmei Zhu、Penghui Hu、Mengying Guo、Linlin Zhao、Linlin Yang、Wei-Jin Gu、Wei Han

  DOI：10.1016/j.cclet.2023.108835

  日期：2024.1

  A general, facile and eco-friendly iron catalysis enables oxidation of unstrained tertiary aromatic alcohols to ketones through C−C bond cleavage even with H2O2 as the oxidant. Notably, this transformation can tolerate oxidation-labile functional groups. The robustness of this method is further demonstrated on the late-stage oxidation of complex bioactive molecules.

  一种通用、简便且环保的铁催化方法，即使使用 H 2 O 2作为氧化剂，也能通过 C−C 键断裂将无张力的叔芳香醇氧化为酮。值得注意的是，这种转化可以耐受氧化不稳定的官能团。该方法的稳健性在复杂生物活性分子的后期氧化中得到进一步证明。
• A Metallomicellar Catalyst for Controlled Oxidation of Alcohols and Lignin Mimics in Water using Open Air as Oxidant
  作者：Prabaharan Thiruvengetam、Pragyansmruti Sunani、Dillip Kumar Chand

  DOI：10.1002/cssc.202301754

  日期：——

  Alcohol groups and β‐O‐4 (C−C) linkages are widespread in biomass feedstock that are abundant renewable resource for value‐added chemicals. The development of sustainable protocols for direct oxidation or oxidative cleavage of feedstock materials in a controlled fashion, using open air as an oxidant is an intellectually stimulating task to produce industrially important value‐added carbonyls. Further, the oxidative depolymerization of lignin into fine chemicals has evoked interest in recent times. Herein, we report the first example of a catalyst system that could activate molecular oxygen from atmospheric air for controlled oxidation and oxidative cleavage/depolymerization of feedstock materials such as alcohols, β‐O‐4 (C−C) linkages and real lignin in water under open air conditions. The selectivity of carbonyl products is controlled by altering the pH between ~7.0 and ~12.0. The current strategy highlights the non‐involvement of any external co‐catalyst, oxidant, radical additives, and/or destructive organic solvents. The catalyst shows a wide substrate scope and eminent functional group tolerance. The upscaled multigram synthesis using an inexpensive catalyst and easily available oxidant evidences the practical utility of the developed protocol. A plausible mechanism has been proposed with the help of a few controlled experiments, and kinetic and computational studies.

  摘要 醇基和 β-O-4 (C-C) 链广泛存在于生物质原料中，它们是丰富的可再生增值化学品资源。利用露天空气作为氧化剂，以可控方式开发原料材料的直接氧化或氧化裂解的可持续方案，是生产具有重要工业价值的羰基化合物的一项具有启发性的任务。此外，将木质素氧化解聚成精细化学品近来也引起了人们的兴趣。在此，我们报告了首个催化剂系统实例，该催化剂系统可激活大气中的分子氧，在露天条件下对醇类、β-O-4（C-C）连接和水中真正的木质素等原料进行受控氧化和氧化裂解/解聚。羰基产物的选择性可通过在 ~7.0 和 ~12.0 之间改变 pH 值来控制。目前的策略突出了不使用任何外部助催化剂、氧化剂、自由基添加剂和/或破坏性有机溶剂的特点。该催化剂具有广泛的底物范围和出色的官能团耐受性。使用廉价的催化剂和易于获得的氧化剂进行多克级合成，证明了所开发方案的实用性。在一些对照实验、动力学和计算研究的帮助下，我们提出了一种合理的机制。