(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol | 1404094-91-2

• 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: (2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
• 英文别名: 4-(hydroxymethyl)-3-methoxyphenylboronic acid pinacol ester；4-Hydroxymethyl-3-methoxyphenylboronic acid pinacol ester；[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol
• CAS: 1404094-91-2
• 化学式: C₁₄H₂₁BO₄
• 分子量: 264.129
• InChiKey: IJIOTDLRHVKZSL-UHFFFAOYSA-N

物化性质

• 沸点：
  387.0±37.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol 在 dibutyltin(II) dilaurate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 [2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl N-[4-(hydroxymethyl)phenyl]carbamate
  参考文献：
  名称：

  Effects of Electronics, Aromaticity, and Solvent Polarity on the Rate of Azaquinone–Methide-Mediated Depolymerization of Aromatic Carbamate Oligomers

  摘要：

  This paper uses physical-organic studies on well-defined oligomers to establish design principles for creating aromatic poly(carbamates) that depolymerize from head-to-tail in low dielectric constant environments when exposed to specific applied signals. We show that either increasing electron density or decreasing the aromaticity of aromatic repeating units in poly(carbamates) increase the overall depolymerization rate. For example, a methoxybenzene-based repeating unit provides depolymerization rates that are 143X faster than oligomers that contain a benzene-based repeating unit. Furthermore, the rate of depolymerization in the methoxybenzene-based system is tolerant to low dielectric environments, whereas the benzene-based oligomers are not.

  DOI：

  10.1021/jo400105m
• 作为产物：
  描述：

  tetrabutylammonium 2‐methoxybenzyl sulfate 在 盐酸 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 17.0h， 生成 (2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
  参考文献：
  名称：

  通过与大量反阳离子的离子对实现普通芳烃结构单元的对选择性 CH 硼酸化

  摘要：

  使用过渡金属催化对芳烃对位的 C-H 键进行选择性官能化是非常具有挑战性的。铱催化硼化已成为芳烃功能化的领先技术，但对位选择性硼化的策略很少，它们在特定的底物类别上运行并使用定制的配体或催化剂。我们描述了一个非常通用的协议，它导致对一些最常见的芳烃构建块（苯胺、苄胺、苯酚、苄醇）产生对位选择性，并使用标准硼酸化配体。我们的策略取决于将底物轻松转化为硫酸盐或氨基磺酸盐，其中阴离子芳烃组分与四丁基铵阳离子配对。我们假设该阳离子的大部分不利于间位 C-H 硼酸化，

  DOI：

  10.1021/jacs.9b07267

文献信息

• Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol release
  作者：R. Adam Mosey、Paul E. Floreancig

  DOI：10.1039/c2ob26571k

  日期：——

  A series of α-alkoxy carbamates that cleave under mild conditions to release alcohols has been synthesized through a multicomponent process. The relationship between structural features in these compounds and the rate of alcohol release in the presence of basic hydrogen peroxide has been studied. The preparation of carbamates that cleave under other conditions has been demonstrated.

  一系列 α-烷氧基氨基甲酸酯在温和条件下裂解以释放醇，已通过多组分工艺合成。这些化合物的结构特征与碱性物质存在下醇释放速率之间的关系过氧化氢已被研究。在其他条件下裂解的氨基甲酸酯的制备已得到证实。
• Qualitative and quantitative point-of-care assays
  申请人：The Penn State Research Foundation

  公开号：US09932360B2

  公开（公告）日：2018-04-03

  Disclosed herein are “equipment-free” flow-through assay devices based on patterned porous media, methods of making same, and methods of using same. The porous, hydrophilic media are patterned with hydrophobic barriers for performing assays on liquids.

  本文披露了基于图案化多孔介质的“无设备”流通测定装置，其制作方法和使用方法。这些多孔的亲水介质被图案化为带有疏水屏障，用于对液体进行测定。
• Terphenyl-Based Small-Molecule Inhibitors of Programmed Cell Death-1/Programmed Death-Ligand 1 Protein–Protein Interaction
  作者：Damian Muszak、Ewa Surmiak、Jacek Plewka、Katarzyna Magiera-Mularz、Justyna Kocik-Krol、Bogdan Musielak、Dominik Sala、Radoslaw Kitel、Malgorzata Stec、Kazimierz Weglarczyk、Maciej Siedlar、Alexander Dömling、Lukasz Skalniak、Tad A. Holak

  DOI：10.1021/acs.jmedchem.1c00957

  日期：2021.8.12
• Phase-Switching Depolymerizable Poly(carbamate) Oligomers for Signal Amplification in Quantitative Time-Based Assays
  作者：Gregory G. Lewis、Jessica S. Robbins、Scott T. Phillips

  DOI：10.1021/ma4007413

  日期：2013.7.9

  This article describes the use of poly(carbamate) oligomers that depolymerize from head-to-tail as phase-switching reagents for increasing the sensitivity of quantitative point-of-care assays that are based on measurements of time. The poly(carbamate) oligomers selectively react with hydrogen peroxide (a model analyte) and provide sensitivity by depolymerizing in the presence of the analyte to convert from water-insoluble oligomers to water-soluble products. This switching reaction enables a sample to wick through a three-dimensional paper-based microfluidic device, where the flow-through time reflects the quantity of the analyte in the sample. Oligomers as short as octamers enable quantitative detection to low nanomolar concentrations of the analyte.
• Ligand- and Substrate-Controlled <i>para</i> C–H Borylation of Anilines at Room Temperature
  作者：Chabush Haldar、Ranjana Bisht、Jagriti Chaturvedi、Saikat Guria、Mirja Md Mahamudul Hassan、Bali Ram、Buddhadeb Chattopadhyay

  DOI：10.1021/acs.orglett.2c03188

  日期：2022.11.11