bis-1,3-(4-bromo-5-t-butylamido-1H-pyrazol-1-yl)propane | 1556785-57-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis-1,3-(4-bromo-5-t-butylamido-1H-pyrazol-1-yl)propane
• 英文别名: 4-bromo-2-[3-[4-bromo-5-(tert-butylcarbamoyl)pyrazol-1-yl]propyl]-N-tert-butylpyrazole-3-carboxamide
• CAS: 1556785-57-9
• 化学式: C₁₉H₂₈Br₂N₆O₂
• 分子量: 532.278
• InChiKey: DFNLTWCYWIOQDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  93.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis-1,3-(4-bromo-5-t-butylamido-1H-pyrazol-1-yl)propane 在 盐酸 、 叔丁基锂 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.67h， 生成 bis-1,3-(4-dihydroxyboryl-5-t-butylamido-1H-pyrazol-1-yl)propane
  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：

  bis-1,3-(4-bromo-1H-pyrazol-1-yl)propane 、 叔丁基异氰酸酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到bis-1,3-(4-bromo-5-t-butylamido-1H-pyrazol-1-yl)propane
  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.