N-iodoacetyl-2-aminophenylboronic acid pinacol ester | 1300115-17-6

• 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-iodoacetyl-2-aminophenylboronic acid pinacol ester
• 英文别名: 2-iodo-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide
• CAS: 1300115-17-6
• 化学式: C₁₄H₁₉BINO₃
• 分子量: 387.025
• InChiKey: ZXDJZMVSWRXTGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-iodoacetyl-2-aminophenylboronic acid pinacol ester 在 4-dimethylaminopyridine 、 BH₃*THF 作用下， 以 四氢呋喃 为溶剂， 生成 (2,6-iPr2-C6H3NHCH2CH2NH(2-pinacolboryl-C6H4)
  参考文献：
  名称：

  Synthesis of trifluoroborate functionalised imidazolium salts as precursors to weakly coordinating bidentate NHC ligands

  摘要：

  A new class of trifluoroborate functionalised N-heterocyclic carbene precursors have been synthesised, isolated and characterised structurally. The ligands were obtained via a serendipitous one-pot reaction in which deprotection, cyclisation and fluorination of boryl-functionalised diarylethylenediamine derivatives occur concurrently. Deprotonation of the imidazolium salts was found to yield the free carbene, though 18-crown-6 was found necessary to prevent further reactivity of the resulting aryl potassium trifluoroborate salts; in the absence of 18-crown-6, elimination of KF resulted in a cyclic carbene-BF2 arene adduct. Complexation to rhodium was facile, and yielded four-coordinate complexes in which the Rh-BF3 interaction was determined by F-19 NMR spectroscopy to be weak. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.12.030
• 作为产物：
  描述：

  N-chloroacetyl-2-aminophenylboronic acid pinacol ester 在 potassium iodide 作用下， 以 丙酮 为溶剂， 以93%的产率得到N-iodoacetyl-2-aminophenylboronic acid pinacol ester
  参考文献：
  名称：

  Synthesis of trifluoroborate functionalised imidazolium salts as precursors to weakly coordinating bidentate NHC ligands

  摘要：

  A new class of trifluoroborate functionalised N-heterocyclic carbene precursors have been synthesised, isolated and characterised structurally. The ligands were obtained via a serendipitous one-pot reaction in which deprotection, cyclisation and fluorination of boryl-functionalised diarylethylenediamine derivatives occur concurrently. Deprotonation of the imidazolium salts was found to yield the free carbene, though 18-crown-6 was found necessary to prevent further reactivity of the resulting aryl potassium trifluoroborate salts; in the absence of 18-crown-6, elimination of KF resulted in a cyclic carbene-BF2 arene adduct. Complexation to rhodium was facile, and yielded four-coordinate complexes in which the Rh-BF3 interaction was determined by F-19 NMR spectroscopy to be weak. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.12.030