N⁴,N⁶-diallyl-pyrimidine-4,6-diyldiamine | 99171-48-9

• 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: N⁴,N⁶-diallyl-pyrimidine-4,6-diyldiamine
• 英文别名: N⁴,N⁶-Diallyl-pyrimidin-4,6-diyldiamin；4-N,6-N-bis(prop-2-enyl)pyrimidine-4,6-diamine
• CAS: 99171-48-9
• 化学式: C₁₀H₁₄N₄
• 分子量: 190.248
• InChiKey: CQJBDTAVJZYUQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N⁴,N⁶-diallyl-pyrimidine-4,6-diyldiamine 、 4,6-二氯嘧啶 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到4-N,6-N-bis(6-chloropyrimidin-4-yl)-4-N,6-N-bis(prop-2-enyl)pyrimidine-4,6-diamine
  参考文献：
  名称：

  Synthesis and Highly Selective Bromination of Azacalix[4]pyrimidine Macrocycles

  摘要：

  A number of N-substituted azacalix[4]pyrimidines were synthesized by two methods. While straightforward condensation reaction between 4,6-dichloropyrimidine and 4,6-bis(alkylamino)-pyrimidines gave identically N-substituted azacalix[4]pyrimidines in low yields, a general and moderate-to-high yielding 1 + 3 macrocyclic fragment coupling reaction afforded azacalix[4]pyrimidines that contained either the same or different N-substituents. Upon treatment with N-bromosuccinimide (NBS) Under controlled conditions, methylazacalix[4]pyrimidine was selectively brominated at lower rim to produce mono-, di-, and tribrominated azacalix[4]pyrimidines in good yields. While azacalix[4]pyrimidine derivatives adopted 1,3-alternate conformation in the solid state, the synthesized macrocycles were fluxional In solution, and the interconversion of various conformational structures was rapid relative to the NMR time scale.

  DOI：

  10.1021/jo902245q
• 作为产物：
  描述：

  4,6-二氯嘧啶 、 丙烯胺 以 水 为溶剂， 反应 12.0h， 以89%的产率得到N⁴,N⁶-diallyl-pyrimidine-4,6-diyldiamine
  参考文献：
  名称：

  Synthesis and Highly Selective Bromination of Azacalix[4]pyrimidine Macrocycles

  摘要：

  A number of N-substituted azacalix[4]pyrimidines were synthesized by two methods. While straightforward condensation reaction between 4,6-dichloropyrimidine and 4,6-bis(alkylamino)-pyrimidines gave identically N-substituted azacalix[4]pyrimidines in low yields, a general and moderate-to-high yielding 1 + 3 macrocyclic fragment coupling reaction afforded azacalix[4]pyrimidines that contained either the same or different N-substituents. Upon treatment with N-bromosuccinimide (NBS) Under controlled conditions, methylazacalix[4]pyrimidine was selectively brominated at lower rim to produce mono-, di-, and tribrominated azacalix[4]pyrimidines in good yields. While azacalix[4]pyrimidine derivatives adopted 1,3-alternate conformation in the solid state, the synthesized macrocycles were fluxional In solution, and the interconversion of various conformational structures was rapid relative to the NMR time scale.

  DOI：

  10.1021/jo902245q

文献信息

• Diuretics. II. Alkoxymercuration by Mixed Anion Salts of Mercury
  作者：Calvert W. Whitehead、John J. Traverso

  DOI：10.1021/ja01542a037

  日期：1958.5
• Synthesis and Highly Selective Bromination of Azacalix[4]pyrimidine Macrocycles
  作者：Li-Xia Wang、De-Xian Wang、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo902245q

  日期：2010.2.5

  A number of N-substituted azacalix[4]pyrimidines were synthesized by two methods. While straightforward condensation reaction between 4,6-dichloropyrimidine and 4,6-bis(alkylamino)-pyrimidines gave identically N-substituted azacalix[4]pyrimidines in low yields, a general and moderate-to-high yielding 1 + 3 macrocyclic fragment coupling reaction afforded azacalix[4]pyrimidines that contained either the same or different N-substituents. Upon treatment with N-bromosuccinimide (NBS) Under controlled conditions, methylazacalix[4]pyrimidine was selectively brominated at lower rim to produce mono-, di-, and tribrominated azacalix[4]pyrimidines in good yields. While azacalix[4]pyrimidine derivatives adopted 1,3-alternate conformation in the solid state, the synthesized macrocycles were fluxional In solution, and the interconversion of various conformational structures was rapid relative to the NMR time scale.