2,4,6-Tris[o-(bromomethyl)phenyl]boroxine | 7481-16-5

• 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: 2,4,6-Tris[o-(bromomethyl)phenyl]boroxine
• 英文别名: o-bromomethylphenylboronic acid anhydride；2-Brommethyl-benzol-1-boronsaeure-anhydrid; Tris-<2-brommethyl-phenyl>-boroxin；'2-Brommethyl-benzol-1-boronsaeure-anhydrid'；o-Brommethyl-benzol-boronsaeure-anhydrid；tris-(2-bromomethyl-phenyl)-cyclotriboroxane；2,4,6-[o-(bromomethyl)phenyl]boroxin；tris-(2-bromomethyl-phenyl)-boroxin；Tris-(2-brommethyl-phenyl)-boroxin；tris(2-bromomethyl phenyl)boroxine；2,4,6-Tris[2-(bromomethyl)phenyl]-1,3,5,2,4,6-trioxatriborinane
• CAS: 7481-16-5
• 化学式: C₂₁H₁₈B₃Br₃O₃
• 分子量: 590.517
• InChiKey: ZORSEKWALBMBTO-UHFFFAOYSA-N

物化性质

• 沸点：
  555.2±60.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-Tris[o-(bromomethyl)phenyl]boroxine 在 氢溴酸 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Chemiluminescent acridinium-9-carboxamide boronic acid probes: Application to a homogeneous glycated hemoglobin assay

  摘要：

  Chemiluminescent acridinium-9-carboxamide probes containing 1, 3, 9, and 27 phenylboronic acids were prepared and their chemiluminescent properties evaluated. The relative chemiluminescent signal from the probes varied from 4 to 0.83 x 10(19) counts/mol across the series, while the apparent affinity of the probes for the diabetes marker glycated hemoglobin increased from 211 to 0.43 mu M. The dose-dependent modulation of the chemiluminescent intensity of the probes upon binding was used to demonstrate a homogeneous assay for glycated hemoglobin. (C) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2005.11.062
• 作为产物：
  描述：

  二邻甲苯基汞 在 H₂O 、 benzoyl peroxide 作用下， 以 四氯化碳 为溶剂， 生成 2,4,6-Tris[o-(bromomethyl)phenyl]boroxine
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219

  摘要：

  DOI：

文献信息

• [EN] SYNTHESIS AND USE OF FLUORINATED COMPOUNDS<br/>[FR] SYNTHÈSE ET UTILISATION DE COMPOSÉS FLUORÉS
  申请人：UNIV PENNSYLVANIA

  公开号：WO2014126990A1

  公开（公告）日：2014-08-21

  The invention is directed to the preparation of fluorinated compounds and their use in organic synthesis. In particular, the invention is directed to methods of reacting compounds of structure with Rf-CH=N2 or (CF3)2C=N2 to form a perfluoroalkylate or -arylated compounds, and products derived from these reactions, where X, YB, and Rf are described herein.

  本发明涉及氟化化合物的制备及其在有机合成中的用途。特别是，本发明涉及将结构式化合物与Rf-CH=N2或(CF3)2C=N2反应以形成全氟烷基或芳基化合物的 methods，以及由此反应得到的产品，其中X，YB和Rf如本文所述。
• Arylboronic Acids. VI. Aminoboronic Anhydrides and a New Heterocycle Containing Boron^1,2
  作者：Richard T. Hawkins、H. R. Snyder

  DOI：10.1021/ja01500a019

  日期：1960.8

  Three o- (dialkylaminomethyl)-benzeneboronic anhydrides are shown to be trimeric. Hydration of the corresponding anhydrides, which do not form complexes with pyridine, provides o-(N-morpholinomethyl)- and o-(dicyclohexylaminomethyl)- benzeneboronic acids. The latter acid shows remarkable stability to acid- catalyzed deboronation as well as dehydration. A new tetracyclic boron- containing heterocycle

  三个邻-(二烷基氨基甲基)-苯硼酸酐显示为三聚体。不与吡啶形成复合物的相应酸酐的水合提供邻-(N-吗啉代甲基)-和邻-(二环己基氨基甲基)-苯硼酸。后一种酸对酸催化的脱硼和脱水显示出显着的稳定性。报道了一种新的四环含硼杂环。讨论了该化合物的结构、邻亚甲基桥连二硝基苯并硼二唑及其一些性质。（授权）
• Diastereoselective Synthesis of Vicinally Bis(trifluoromethylated) Alkylboron Compounds through Successive Insertions of 2,2,2-Trifluorodiazoethane
  作者：Gary A. Molander、DaWeon Ryu

  DOI：10.1002/anie.201408191

  日期：2014.12.15

  development of diverse methods for incorporating this functional group. A recently reported route to α‐trifluoromethylated alkylboron compounds by an α‐transfer mechanism has now been extended to the synthesis of unprecedented, vicinally ditrifluoromethylated alkylboron compounds in a diastereoselective fashion. The utility of these products is highlighted by conversion of the CB bond into other functional

  嵌入的CF 3取代基在有机亚结构内的有用性，需要开发各种方法来引入该官能团。最近报道的一种通过α-转移机制合成α-三氟甲基化烷基硼化合物的途径现已扩展到以非对映选择性的方式合成前所未有的，毒的二三氟甲基化烷基硼化合物。这些产品的实用性通过将CB键转换为其他官能团来突出。
• Novel fluorescence sensor for ‘small’ saccharides
  作者：Tony D. James、Hideyuki Shinmori、Seiji Shinkai

  DOI：10.1039/a606552j

  日期：——

  The small binding pocket of compound 2 can exclude ‘large’ saccharides such as D-glucose, whereas ‘small’ saccharides such as D-sorbitol are strongly bound as 1:1 complexes; the binding events can be sensitively monitored by changes in the fluorescence intensity.

  化合物 2 的小结合口袋可以排除 D-葡萄糖等 "大 "糖类，而 D-山梨醇等 "小 "糖类则以 1:1 复合物的形式与之紧密结合；通过荧光强度的变化可以灵敏地监测结合事件。
• Synthesis and evaluation of D-glucosamine-selective fluorescent sensors
  作者：Christopher R. Cooper、Tony D. James

  DOI：10.1039/a909145i

  日期：——

  Fluorescent PET (photoinduced electron transfer) sensors 11a and 11b with monoaza-18-crown-6 or monoaza-15-crown-5 ether and boronic acid receptor units are synthesised.

  合成了具有单aza-18-冠醚-6 或单aza-15-冠醚-5 和硼酸受体单元的荧光 PET（光诱导电子转移）传感器 11a 和 11b。