3,5-bis(adamantyl)-1H-pyrazole | 125995-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-bis(adamantyl)-1H-pyrazole
• 英文别名: 3,5-diadamantylpyrazole；1H-Pyrazole, 3,5-bis(tricyclo[3.3.1.1(3,7)]dec-1-yl)-；3,5-bis(1-adamantyl)-1H-pyrazole
• CAS: 125995-71-3
• 化学式: C₂₃H₃₂N₂
• 分子量: 336.52
• InChiKey: MGNNXEJYJDULCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-bis(adamantyl)-1H-pyrazole 、 二溴甲烷 在 苄基三乙基氯化铵 、 potassium carbonate 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以95%的产率得到bapm
  参考文献：
  名称：

  New mononuclear Pd(II) complexes of sterically hindered bispyrazolylmethanes

  摘要：

  Three new palladium(II) complexes incorporating the bispyrazolylmethane core have been synthesised and fully characterised in the solution and solid state. Single crystal X-ray studies revealed almost complete blocking of the upper face of the palladium ion by the substituents at the 3- and 5-positions of the pyrazole rings. Preliminary screening of the complexes for palladium(II) mediated catalysis revealed good catalytic activity for the Heck coupling reaction. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.09.016
• 作为产物：
  描述：

  1,3-bis(tricyclo[3.3.1.1(3,7)]dec-1-yl)propan-1,3-dione 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以81%的产率得到3,5-bis(adamantyl)-1H-pyrazole
  参考文献：
  名称：

  New mononuclear Pd(II) complexes of sterically hindered bispyrazolylmethanes

  摘要：

  Three new palladium(II) complexes incorporating the bispyrazolylmethane core have been synthesised and fully characterised in the solution and solid state. Single crystal X-ray studies revealed almost complete blocking of the upper face of the palladium ion by the substituents at the 3- and 5-positions of the pyrazole rings. Preliminary screening of the complexes for palladium(II) mediated catalysis revealed good catalytic activity for the Heck coupling reaction. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2009.09.016

文献信息

• Synthesis of 3-(1-Adamantyl)pyrazole and 3,5-Di(1-adamantyl)pyrazole in a Microwave Oven
  作者：Isabelle Forfar、Pilar Cabildo、Rosa María Claramunt、José Elguero

  DOI：10.1246/cl.1994.2079

  日期：1994.11

  An extraordinary inversion of the regioselectivity in the reaction of C-adamantylation of pyrazoles by 1-bromoadamantane was observed when the autoclave vessel was replaced by a microwave oven. In these last conditions mono and disubstituted 3(5)-(1-adamantyl) pyrazoles were obtained.

  当用微波炉代替高压釜时，1-溴金刚烷对吡唑进行 C-金刚烷化反应的区域选择性发生了奇特的逆转。在最后这些条件下，得到了单取代和二取代的 3(5)-(1-金刚烷基) 吡唑。
• Yalpani, Mohamed; Boese, Roland; Koester, Roland, Chemische Berichte, 1990, vol. 123, p. 1275 - 1284
  作者：Yalpani, Mohamed、Boese, Roland、Koester, Roland

  DOI：——

  日期：——
• YALPANI, MOHAMED;BOESE, ROLAND;KOSTER, ROLAND, CHEM. BER., 123,(1990) N, C. 1275-1283
  作者：YALPANI, MOHAMED、BOESE, ROLAND、KOSTER, ROLAND

  DOI：——

  日期：——
• New mononuclear Pd(II) complexes of sterically hindered bispyrazolylmethanes
  作者：Michael W. Jones、Robert M. Adlington、Jack E. Baldwin、Delphine D. Le Pevelen、Nicolas Smiljanic

  DOI：10.1016/j.ica.2009.09.016

  日期：2010.4

  Three new palladium(II) complexes incorporating the bispyrazolylmethane core have been synthesised and fully characterised in the solution and solid state. Single crystal X-ray studies revealed almost complete blocking of the upper face of the palladium ion by the substituents at the 3- and 5-positions of the pyrazole rings. Preliminary screening of the complexes for palladium(II) mediated catalysis revealed good catalytic activity for the Heck coupling reaction. (C) 2009 Elsevier B.V. All rights reserved.