2, 6-dichloro-7-(2, 2, 2-trifluoroethyl)-7H-purine | 1227047-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2, 6-dichloro-7-(2, 2, 2-trifluoroethyl)-7H-purine
• 英文别名: 2,6-Dichloro-7-(2,2,2-trifluoroethyl)-7H-purine；2,6-dichloro-7-(2,2,2-trifluoroethyl)purine
• CAS: 1227047-31-5
• 化学式: C₇H₃Cl₂F₃N₄
• 分子量: 271.029
• InChiKey: QXLVAISNZXCKGB-UHFFFAOYSA-N

物化性质

• 沸点：
  266.0±50.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2, 6-dichloro-7-(2, 2, 2-trifluoroethyl)-7H-purine 、 5-(1,1-二甲基乙基)-2-甲基苯胺 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 生成 N-(5-(tert-butyl)-2-methylphenyl)-2-chloro-7-(2,2,2-trifluoroethyl)-7H-purin-6-amine
  参考文献：
  名称：

  Purine derivatives as potent γ-secretase modulators

  摘要：

  The development of a novel series of purines as gamma-secretase modulators for potential use in the treatment of Alzheimer's disease is disclosed herein. Optimization of a previously disclosed pyrimidine series afforded a series of potent purine-based gamma-secretase modulators with 300- to 2000-fold in vitro selectivity over inhibition of Notch cleavage and that selectively reduces A beta 42 in an APP-YAC transgenic mouse model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.008
• 作为产物：
  描述：

  trifluoromethyl 2,2,2-trifluoroethylsulfonate 、 2,6-二氯嘌呤 在 甲基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以74%的产率得到2, 6-dichloro-7-(2, 2, 2-trifluoroethyl)-7H-purine
  参考文献：
  名称：

  Direct, Regioselective N-Alkylation of 1,3-Azoles

  摘要：

  Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.

  DOI：

  10.1021/acs.orglett.5b02994

文献信息

• Direct, Regioselective <i>N</i>-Alkylation of 1,3-Azoles
  作者：Shuai Chen、Russell F. Graceffa、Alessandro A. Boezio

  DOI：10.1021/acs.orglett.5b02994

  日期：2016.1.4

  Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.
• Purine derivatives as potent γ-secretase modulators
  作者：Alexey Rivkin、Sean P. Ahearn、Stephanie M. Chichetti、Christopher L. Hamblett、Yudith Garcia、Michelle Martinez、Jed L. Hubbs、Michael H. Reutershan、Matthew H. Daniels、Phieng Siliphaivanh、Karin M. Otte、Chaomin Li、Andrew Rosenau、Laura M. Surdi、Joon Jung、Bethany L. Hughes、Jamie L. Crispino、George N. Nikov、Richard E. Middleton、Christopher M. Moxham、Alexander A. Szewczak、Sanjiv Shah、Lily Y. Moy、Candia M. Kenific、Flobert Tanga、Jonathan C. Cruz、Paula Andrade、Minilik H. Angagaw、Nirah H. Shomer、Thomas Miller、Benito Munoz、Mark S. Shearman

  DOI：10.1016/j.bmcl.2010.02.008

  日期：2010.4

  The development of a novel series of purines as gamma-secretase modulators for potential use in the treatment of Alzheimer's disease is disclosed herein. Optimization of a previously disclosed pyrimidine series afforded a series of potent purine-based gamma-secretase modulators with 300- to 2000-fold in vitro selectivity over inhibition of Notch cleavage and that selectively reduces A beta 42 in an APP-YAC transgenic mouse model. (C) 2010 Elsevier Ltd. All rights reserved.