4-N,6-N-bis(6-chloropyrimidin-4-yl)-4-N,6-N-bis[(4-methoxyphenyl)methyl]pyrimidine-4,6-diamine | 1206706-17-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-N,6-N-bis(6-chloropyrimidin-4-yl)-4-N,6-N-bis[(4-methoxyphenyl)methyl]pyrimidine-4,6-diamine
• CAS: 1206706-17-3
• 化学式: C₂₈H₂₄Cl₂N₈O₂
• 分子量: 575.457
• InChiKey: MBNLKONSVBQTKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-N,6-N-bis(6-chloropyrimidin-4-yl)-4-N,6-N-bis[(4-methoxyphenyl)methyl]pyrimidine-4,6-diamine 、 N4,N6-二甲基嘧啶-4,6-二胺 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.0h， 以51%的产率得到2,8-Bis[(4-methoxyphenyl)methyl]-14,20-dimethyl-2,4,6,8,10,12,14,16,18,20,22,24-dodecazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene
  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 、 4,6-bis(para-methoxybenzylamino)pyrimidine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到4-N,6-N-bis(6-chloropyrimidin-4-yl)-4-N,6-N-bis[(4-methoxyphenyl)methyl]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

文献信息

• 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.