diisopropyl 1-(3-fluoro-4-hydroxyphenyl)-1,2-hydrazinedicarboxylate

• 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: diisopropyl 1-(3-fluoro-4-hydroxyphenyl)-1,2-hydrazinedicarboxylate
• 英文别名: propan-2-yl N-(3-fluoro-4-hydroxyphenyl)-N-(propan-2-yloxycarbonylamino)carbamate
• 化学式: C₁₄H₁₉FN₂O₅
• 分子量: 314.314
• InChiKey: APMJFGMHMNTTKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氟苯酚 、 偶氮二甲酸二异丙酯 在 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以83%的产率得到diisopropyl 1-(3-fluoro-4-hydroxyphenyl)-1,2-hydrazinedicarboxylate
  参考文献：
  名称：

  ZrCl4促进卤代酚的亲电子胺化过程中的卤素迁移。

  摘要：

  首次证明了在ZrCl4作为路易斯酸的存在下，卤化苯酚与二异丙基二氮杂二羧酸酯的亲电胺化反应，并伴随着卤素的迁移。氟，氯，溴或碘原子在胺化过程中在温和的反应条件下迁移。

  DOI：

  10.1039/b203622c

文献信息

• ZrCl4-promoted halogen migration during an electrophilic amination of halogenated phenolsElectronic supplementary information (ESI) available: spectroscopic data (1H NMR,13C NMR, IR, MS), mp and elemental analysis (or HRMS) for the products 3 and 4. See http://www.rsc.org/suppdata/cc/b2/b203622c/Dedicated to Professor Waldemar Adam, University of Würzburg, Germany, on the occasion of his 65th birthday.
  作者：Sergeja Bombek、Roman Lenaršič、Marijan Kočevar、Laurent Saint-Jalmes、Jean-Roger Desmurs、Slovenko Polanc

  DOI：10.1039/b203622c

  日期：2002.7.1

  An electrophilic amination of halogenated phenols with diisopropyl diazenedicarboxylate in the presence of ZrCl4 as a Lewis acid, accompanied by a halogen migration, was demonstrated for the first time; the fluorine, chlorine, bromine, or iodine atom migrated during the amination process under mild reaction conditions.

  首次证明了在ZrCl4作为路易斯酸的存在下，卤化苯酚与二异丙基二氮杂二羧酸酯的亲电胺化反应，并伴随着卤素的迁移。氟，氯，溴或碘原子在胺化过程中在温和的反应条件下迁移。
• Electrophilic Amination of 4-Fluorophenol with Diazenes:  A Complete Removal of the Fluorine Atom
  作者：Sergeja Bombek、Franc Požgan、Marijan Kočevar、Slovenko Polanc

  DOI：10.1021/jo035856b

  日期：2004.3.1

  The electrophilic amination of 2-fluorophenol, 4-fluorophenol, and 2-chlorophenol was observed to occur as a result of their treatment with diazenes 1-4 under mild reaction conditions in the presence of ZrCl4. The products originating from the 2-fluorophenol or 2-chlorophenol can be considered as "normal" products of amination. On the other hand, the 2-chloro-4-amino-substituted phenols obtained from the 4-fluorophenol seem to be formed in a process that involves an ipso amination, the complete removal of the fluorine atom, and the introduction of the chlorine atom.