N-(1-allylcycloheptyl)-4,6-dichloropyrimidin-2-amine | 1609548-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-(1-allylcycloheptyl)-4,6-dichloropyrimidin-2-amine
• CAS: 1609548-00-6
• 化学式: C₁₄H₁₉Cl₂N₃
• 分子量: 300.231
• InChiKey: DIVFXTHMIXLJKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  37.81
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(1-allylcycloheptyl)-4,6-dichloropyrimidin-2-amine 在 2,6-二甲基吡啶 、 过氧化双月桂酰 作用下， 以 乙酸乙酯 为溶剂， 生成 6'-chloro-4'-(2,2,2-trifluoroethyl)-3',4'-dihydrospiro[cycloheptane-1,2'-pyrimido[1,2-a]pyrimidin]-8'-(1'H)-one 、 4-chloro-11-(4,4,4-trifluorobutyl)-7,8,9,10,11,12-hexahydro-6,11-methanopyrimido[1,2-a][1,3]diazonin-2-(6H)-one
  参考文献：
  名称：

  Carbon Radical Attack on a Pyrimidine Nitrogen. An Unusual Entry into Polycyclic Aminopyrimidones

  摘要：

  Unprecedented examples of a synthetically useful radical ring closure onto a pyrimidine nitrogen leading to novel, highly functionalized bi- and tricyclic pyrimidone structures are reported. An unexpected hydrogen atom translocation prior to the cyclization step was observed in some cases.

  DOI：

  10.1021/ol501104h
• 作为产物：
  描述：

  2,4,6-三氯嘧啶 、 1-Prop-2-enylcycloheptan-1-amine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以19%的产率得到N-(1-allylcycloheptyl)-4,6-dichloropyrimidin-2-amine
  参考文献：
  名称：

  Carbon Radical Attack on a Pyrimidine Nitrogen. An Unusual Entry into Polycyclic Aminopyrimidones

  摘要：

  Unprecedented examples of a synthetically useful radical ring closure onto a pyrimidine nitrogen leading to novel, highly functionalized bi- and tricyclic pyrimidone structures are reported. An unexpected hydrogen atom translocation prior to the cyclization step was observed in some cases.

  DOI：

  10.1021/ol501104h

文献信息

• Radical-Based Route to 2-(Trifluoromethyl)-1,3,4-oxadiazoles and Trifluoromethyl-Substituted Polycyclic 1,2,4-Triazoles and Dihydrofurans
  作者：Ling Qin、Samir Z. Zard

  DOI：10.1021/acs.orglett.5b00457

  日期：2015.3.20

  O-Ethyl S-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl xanthate was readily prepared on a large scale and shown to undergo very efficient intermolecular radical additions to unactivated alkenes. The products were further elaborated by exploiting both radical and ionic processes to provide a variety of trifluoromethyl-substituted derivatives, including medicinally relevant triazoles. In particular, the application of a radical allylation on the initial adducts leads to structures that are able to undergo intramolecular [4 + 2] cycloaddition reactions.