4-Methoxybenzendiazoniumtetraphenylborat | 3855-89-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4-Methoxybenzendiazoniumtetraphenylborat
• 英文别名: 4-methoxybenzenediazonium tetraphenylborate；4-Methoxybenzenediazonium;tetraphenylboranuide
• CAS: 3855-89-8
• 化学式: C₇H₇N₂O*C₂₄H₂₀B
• 分子量: 454.379
• InChiKey: XMGIODKDYHOJEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-Methoxybenzendiazoniumtetraphenylborat 以 二氯甲烷 、 甲苯 为溶剂， 生成 6-acetyl-2-(4-methoxyphenyl)-5-methyl-3,3-diphenyl-4H-1,2,4,3λ4-triazaborine
  参考文献：
  名称：

  Novel 5-(4-Substituted-phenyldiazenyl)-1,3,2λ⁴-oxazaborines and Their Rearrangement to 1,2,4,3λ⁴-Triazaborines

  摘要：

  The reaction of substituted benzenediazonium tetraphenylborates with the beta-enaminones derived from pentane-2,4-dione, 1-phenylbutane-1,3-dione, and 1,4-diphenylbutane-1,3-dione with a primary or secondary (N-methyl, N-phenyl) amino group in CH2Cl2 gives 5-(substituted-phenyldiazenyl)-2,2-diphenyl-4,6-disubstituted- 1,3,2 lambda(4)-oxazaborines or 5-(substituted-phenyldiazenyl)-2,2-diphenyl-3,4,6-trisubstituted-1,3,2 lambda(4)- oxazaborines, respectively. The reaction intermediate of these compounds has been identified, and a mechanism for the reaction has been suggested. Substituted 1,3,2 lambda(4)-oxazaborines gradually rearrange into 1,2,4,3 lambda(4)-triazaborines at temperatures above 100 degrees C.

  DOI：

  10.1021/om051078x

文献信息

• Synthesis, Structure, and Reactivity of Anionic sp²-sp³Diboron Compounds: Readily Accessible Boryl Nucleophiles
  作者：Sabrina Pietsch、Emily C. Neeve、David C. Apperley、Rüdiger Bertermann、Fanyang Mo、Di Qiu、Man Sing Cheung、Li Dang、Jianbo Wang、Udo Radius、Zhenyang Lin、Christian Kleeberg、Todd B. Marder

  DOI：10.1002/chem.201500235

  日期：2015.5.4

  Lewis bases, such as alkoxides and fluoride. The study was extended to alternative Lewis bases, such as acetate, and other diboron reagents. The B(sp2)–B(sp3) adducts exhibit two distinct boron environments in the solid‐state and solution NMR spectra, except for [(4‐tBuC6H4O)B2pin2]−, which shows rapid site exchange in solution. DFT calculations were performed to analyze the stability of the adducts with

  四烷氧基二硼化合物的路易斯碱加合物，特别是双（频哪醇）二硼（B 2 pin 2），已被提议作为无金属硼化反应中亲核硼基物种的活性来源。我们报告了一系列B 2 pin 2与硬路易斯碱（如醇盐和氟化物）的阴离子加合物的分离和详细的结构表征（通过固态和溶液NMR光谱法和X射线晶体学）。该研究扩展至其他路易斯碱，例如乙酸盐和其他二硼试剂。B（sp 2）–B（sp 3）加合物在固态和溶液NMR光谱中表现出两个不同的硼环境，除了[（4- tBuC 6 H 4 O）B 2销2 ] -，显示溶液中的快速位点交换。进行DFT计算以分析加合物相对于解离的稳定性。分离的加合物与两个代表性的有机亲电试剂系列（即芳基卤化物和重氮盐）的化学计量反应表明，阴离子型二硼化合物作为亲核性硼基阴离子源具有相对活性。
• New Triazaborine Chromophores: Their Synthesis via Oxazaborines and Electrochemical and DFT Study of Their Fundamental Properties
  作者：František Josefík、Tomáš Mikysek、Markéta Svobodová、Petr Šimůnek、Hana Kvapilová、Jiří Ludvík

  DOI：10.1021/om500219g

  日期：2014.9.22
• A new bicyclic oxazaborines with a bridged nitrogen atom, their thermic rearrangement and fluorescence properties
  作者：František Josefík、Markéta Svobodová、Valerio Bertolasi、Petr Šimůnek、Vladimír Macháček、Numan Almonasy、Eva Černošková

  DOI：10.1016/j.jorganchem.2011.11.004

  日期：2012.2

  Cyclic beta-enaminones bearing secondary amino group react with 4-substituted benzenediazonium tetraphenylborates in dichloromethane to form substituted bicyclic [1,3,2 lambda(4)] oxazaborines The oxazaborines rearrange, on heating to 200 degrees C in the absence of solvent or in DMF or DMSO, to isomeric 2H-[1,2,4,3 lambda(4)] triazaborines. Previously prepared [1,3,2 lambda(4)] oxazaborines derived from acyclic beta-enaminones bearing secondary amino group either did not undergo the rearrangement or with a lot of difficulties and with negligible yield. The fluorescence behaviour of the prepared triazaborines was observed. These compounds fluoresce in 2-methyltetrahydrofurane and in solid state under low temperatures. (C) 2011 Elsevier B.V. All rights reserved.
• Rehorek, Detlef; Marx, Joerg, Journal fur praktische Chemie (Leipzig 1954), 1980, vol. 322, # 6, p. 872 - 876
  作者：Rehorek, Detlef、Marx, Joerg

  DOI：——

  日期：——