N,N-di-Boc-2-bromo-4-fluoroaniline | 880384-48-5

• 物质功能分类: 有机原料 - 氨基化合物
• 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: N,N-di-Boc-2-bromo-4-fluoroaniline
• 英文别名: 1,3-Bis(1,1-dimethylethyl) 2-(2-bromo-4-fluorophenyl)imidodicarbonate；tert-butyl N-(2-bromo-4-fluorophenyl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 880384-48-5
• 化学式: C₁₆H₂₁BrFNO₄
• 分子量: 390.249
• InChiKey: UYSTZBMKUZQDQM-UHFFFAOYSA-N

物化性质

• 沸点：
  397.686±52.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.360±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N-di-Boc-2-bromo-4-fluoroaniline 在 四(三苯基膦)钯 potassium carbonate 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 (4-fluoro-2-vinylphenyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes

  摘要：

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

  DOI：

  10.1021/jo048723e
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-溴-4-氟苯胺 以 四氢呋喃 为溶剂， 以62%的产率得到N,N-di-Boc-2-bromo-4-fluoroaniline
  参考文献：
  名称：

  Short and Simple Preparation ofN-Boc-Protected Anthranilic Acidtert-Butyl Esters from 2-Bromo-Anilines

  摘要：

  本文描述了一种从邻溴苯胺制备二保护氨基苯甲酸衍生物的新型两步程序。

  DOI：

  10.1055/s-2005-921910

文献信息

• Determination of the Hammett Acidity of HF/Base Reagents
  作者：Mélissa Longuet、Kassandra Vitse、Agnès Martin-Mingot、Bastien Michelet、Frédéric Guégan、Sébastien Thibaudeau

  DOI：10.1021/jacs.4c02344

  日期：2024.5.1

  Harnessing the acidity of HF/base reagents is of paramount importance to improve the efficiency and selectivity of fluorination reactions. Yet, no general method has been reported to evaluate their acidic properties, and experimental designs are still relying on a trial-and-error approach. We report a new method based on 19F NMR spectroscopy which allows highly sensitive measures and short-time analyses

  利用 HF/碱试剂的酸性对于提高氟化反应的效率和选择性至关重要。然而，尚未报道评估其酸性特性的通用方法，并且实验设计仍然依赖于试错法。我们报告了一种基于19 F NMR 光谱的新方法，可实现高灵敏度测量和短时间分析。有利的是，指标的基本属性可以通过DFT计算在上游确定，从而提供简单而稳健的半经验方法。特别是，本研究中使用的指标经过合理设计，符合概念上吸引人且常用的哈米特量表。该方法已应用于市售和最近开发的 HF/碱试剂。
• AN IMPROVED SYNTHESIS OF<i>N</i>-BOC PROTECTED ARYL AMINES
  作者：Shelley Darnbrough、Miljenko Mervic、Stephen M. Condon、Christopher J. Burns

  DOI：10.1081/scc-100106036

  日期：2001.1

  There are several known methods of protecting amines as their Boc derivatives. For less nucleophilic amines such as aryl amines these methods often give poor yields and are generally not satisfactory. Here, Boc aryl amines are obtained by first introducing two Boc groups followed by selective removal of one of them. This procedure works well for a number highly sterically hindered substrates as well as electron deficient and electron rich aryl amines.