bis-1,2-(4-bromo-1H-pyrazol-1-yl)ethane | 116476-96-1

• 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-1,2-(4-bromo-1H-pyrazol-1-yl)ethane
• 英文别名: 1,2-bis(4-bromopyrazol-1-yl)ethane；4-Bromo-1-[2-(4-bromopyrazol-1-yl)ethyl]pyrazole
• CAS: 116476-96-1
• 化学式: C₈H₈Br₂N₄
• 分子量: 319.986
• InChiKey: KAJMMDZYVIQBIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C(Solv: ethanol (64-17-5))
• 沸点：
  414.8±30.0 °C(Predicted)
• 密度：
  1.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-1,2-(4-bromo-1H-pyrazol-1-yl)ethane 在 盐酸 、 叔丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.67h， 生成 bis-1,2-(4-dihydroxyboryl-5-t-butylamido-1H-pyrazol-1-yl)ethane
  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
• 作为产物：
  描述：

  1,2-bis(pyrazol-1-yl)ethane 、 溴 以86%的产率得到
  参考文献：
  名称：

  TORRES, J.;LAVANDERA, J. L.;CABILDO, P.;CLARAMUNT, R. M.;ELGUERO, J., J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 771-782

  摘要：

  DOI：

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.
• TORRES, J.;LAVANDERA, J. L.;CABILDO, P.;CLARAMUNT, R. M.;ELGUERO, J., J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 771-782
  作者：TORRES, J.、LAVANDERA, J. L.、CABILDO, P.、CLARAMUNT, R. M.、ELGUERO, J.

  DOI：——

  日期：——