bis-1,3-(4-bromo-1H-pyrazol-1-yl)propane | 1556785-36-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: bis-1,3-(4-bromo-1H-pyrazol-1-yl)propane
• 英文别名: 4-Bromo-1-[3-(4-bromopyrazol-1-yl)propyl]pyrazole；4-bromo-1-[3-(4-bromopyrazol-1-yl)propyl]pyrazole
• CAS: 1556785-36-4
• 化学式: C₉H₁₀Br₂N₄
• 分子量: 334.013
• InChiKey: NLYJFPFAPKVBGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis-1,3-(4-bromo-1H-pyrazol-1-yl)propane 在 叔丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成
  参考文献：
  名称：

  Formation of dilithiated bis-(1H-pyrazol-1-yl)alkanes and their application in the synthesis of diboronic acids

  摘要：

  Bis-(1H-pyrazol-1-yl)alkanes were deprotonated at the pyrazole 5-positions on treatment with LDA in THF at low temperature. These dianions reacted with tert-butylisocyanate as the electrophile to install a tert-butylamide group at the pyrazole 5-position. The obtained amides were next converted into the respective diboronic acids by Br-Li exchange with t-BuLi in THF at low temperature, followed by the use of triethyl borate as the electrophile. The X-ray analysis of the obtained diboronic acids revealed the presence of a variety of structural motifs, which stabilize the structure by hydrogen bond formation. The stabilization pattern differs greatly with a minor modification of the linker connecting the pyrazole rings. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.007

文献信息

• Formation of dilithiated bis-(1H-pyrazol-1-yl)alkanes and their application in the synthesis of diboronic acids
  作者：Krzysztof Durka、Agnieszka Górska、Tomasz Kliś、Janusz Serwatowski、Krzysztof Woźniak

  DOI：10.1016/j.tetlet.2014.01.007

  日期：2014.2

  Bis-(1H-pyrazol-1-yl)alkanes were deprotonated at the pyrazole 5-positions on treatment with LDA in THF at low temperature. These dianions reacted with tert-butylisocyanate as the electrophile to install a tert-butylamide group at the pyrazole 5-position. The obtained amides were next converted into the respective diboronic acids by Br-Li exchange with t-BuLi in THF at low temperature, followed by the use of triethyl borate as the electrophile. The X-ray analysis of the obtained diboronic acids revealed the presence of a variety of structural motifs, which stabilize the structure by hydrogen bond formation. The stabilization pattern differs greatly with a minor modification of the linker connecting the pyrazole rings. (C) 2014 Elsevier Ltd. All rights reserved.