| 1535484-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• CAS: 1535484-10-6
• 化学式: C₁₅H₁₃F₃N₄
• 分子量: 306.29
• InChiKey: XYCIZYRLYPXEAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,5-bis(trifluoromethyl)phenyl azide 、 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以72%的产率得到N1,N3-bis[3,5-bis(trifluoromethyl)phenyl]-2-(9-isopropyl-9H-purin-6-yl)-5-(trifluoromethyl)benzene-1,3-diamine
  参考文献：
  名称：

  Hydrogen-Bond-Assisted Controlled C–H Functionalization via Adaptive Recognition of a Purine Directing Group

  摘要：

  We have developed the Rh-catalyzed selective C-H functionalization of 6-arylpurines, in which the purine moiety directs the C-H bond activation of the aryl pendant. While the first C-H amination proceeds via the N1-chelation assistance, the subsequent second C-H bond activation takes advantage of an intramolecular hydrogen-bonding interaction between the initially formed amino group and one nitrogen atom, either N1 or N7, of the purinyl part. Isolation of a rhodacycle intermediate and the substrate variation studies suggest that N1 is the main active site for the C-H functionalization of both the first and second amination in 6-arylpurines, while N7 plays an essential role in controlling the degree of functionalization serving as an intramolecular hydrogen-bonding site in the second amination process. This pseudo-Curtin-Hammett situation was supported by density functional calculations, which suggest that the intramolecular hydrogen-bonding capability helps second amination by reducing the steric repulsion between the first installed ArNH and the directing group.

  DOI：

  10.1021/ja4118472

文献信息

• Rhodium(<scp>iii</scp>)-catalyzed CF₃-carbenoid C–H functionalization of 6-arylpurines
  作者：Daria V. Vorobyeva、Mikhail M. Vinogradov、Yulia V. Nelyubina、Dmitry A. Loginov、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1039/c8ob00645h

  日期：——

  An efficient method for the CF3-carbenoid C–H functionalization of 6-arylpurines has been developed. This protocol uses readily available methyl 3,3,3-trifluoro-2-diazopropionate as a cross-coupling partner and proceeds smoothly under chelation-controlled Rh(III) catalysis. The reactions provide the corresponding carbene insertion products with high regioselectivity within a few hours and allow the

  已经开发出一种有效的方法，用于将6-芳基嘌呤的CF 3-类胡萝卜素C–H功能化。该协议使用易于获得的3,3,3-三氟-2-重氮丙酸甲酯作为交叉偶联伴侣，并在螯合控制的Rh（III）催化下顺利进行。该反应在数小时内为相应的卡宾插入产物提供了高区域选择性，并允许将CF 3和羧酸盐功能引入生物学上重要的嘌呤分子，包括核苷衍生物。