2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-bioxaborolan-2-yl)benzoic acid | 1031857-96-1

• 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: 2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-bioxaborolan-2-yl)benzoic acid
• 英文别名: 3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
• CAS: 1031857-96-1
• 化学式: C₁₃H₁₅BF₂O₄
• 分子量: 284.068
• InChiKey: CLYXVWDLNOWTQF-UHFFFAOYSA-N

物化性质

• 沸点：
  373.6±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-bioxaborolan-2-yl)benzoic acid 、 tert-butyl (5-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)pentyl)carbamate 在 三氟乙酸 、 吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以60%的产率得到3,5-difluoro-N-(5-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)pentyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and characterization of 2,6-difluoro-4-carboxyphenylboronic acid and a biotin derivative thereof as captors of anionic aqueous [18F]-fluoride for the preparation of [18F/19F]-labeled aryltrifluoroborates with high kinetic stability

  摘要：

  Arylboronic esters are readily converted to aryltrifluoroborates in the presence of aqueous fluoride. As such these represent attractive synthetic precursors that afford one-step labeling with [F-18]-fluoride for the generation of PET reagents. Herein we present the synthesis of a heretofore undisclosed arylboronic ester that is converted to its corresponding trifluoroborate. Essential for contemplating its use in PET imaging is the demonstration of kinetic resistance to solvolytic defluoridation. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.03.021
• 作为产物：
  描述：

  频哪醇 、 4-硼-3,5-二氟苯甲酸 以 四氢呋喃 、 甲苯 为溶剂， 以100%的产率得到2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-bioxaborolan-2-yl)benzoic acid
  参考文献：
  名称：

  Synthesis and characterization of 2,6-difluoro-4-carboxyphenylboronic acid and a biotin derivative thereof as captors of anionic aqueous [18F]-fluoride for the preparation of [18F/19F]-labeled aryltrifluoroborates with high kinetic stability

  摘要：

  Arylboronic esters are readily converted to aryltrifluoroborates in the presence of aqueous fluoride. As such these represent attractive synthetic precursors that afford one-step labeling with [F-18]-fluoride for the generation of PET reagents. Herein we present the synthesis of a heretofore undisclosed arylboronic ester that is converted to its corresponding trifluoroborate. Essential for contemplating its use in PET imaging is the demonstration of kinetic resistance to solvolytic defluoridation. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.03.021

文献信息

• Synthesis and characterization of 2,6-difluoro-4-carboxyphenylboronic acid and a biotin derivative thereof as captors of anionic aqueous [18F]-fluoride for the preparation of [18F/19F]-labeled aryltrifluoroborates with high kinetic stability
  作者：Curtis W. Harwig、Richard Ting、Michael J. Adam、Thomas J. Ruth、David M. Perrin

  DOI：10.1016/j.tetlet.2008.03.021

  日期：2008.5

  Arylboronic esters are readily converted to aryltrifluoroborates in the presence of aqueous fluoride. As such these represent attractive synthetic precursors that afford one-step labeling with [F-18]-fluoride for the generation of PET reagents. Herein we present the synthesis of a heretofore undisclosed arylboronic ester that is converted to its corresponding trifluoroborate. Essential for contemplating its use in PET imaging is the demonstration of kinetic resistance to solvolytic defluoridation. (C) 2008 Published by Elsevier Ltd.