25,27-Dibromo-2,8,14,20-tetramethyl-2,4,6,8,10,12,14,16,18,20,22,24-dodecazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene | 1206706-35-5

• 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: 25,27-Dibromo-2,8,14,20-tetramethyl-2,4,6,8,10,12,14,16,18,20,22,24-dodecazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
• CAS: 1206706-35-5
• 化学式: C₂₀H₁₈Br₂N₁₂
• 分子量: 586.251
• InChiKey: OULMBCPDBOTPRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  25-Bromo-2,8,14,20-tetramethyl-2,4,6,8,10,12,14,16,18,20,22,24-dodecazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 5.0h， 以100%的产率得到25,27-Dibromo-2,8,14,20-tetramethyl-2,4,6,8,10,12,14,16,18,20,22,24-dodecazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene
  参考文献：
  名称：

  固有手性的1，3-交替Azacalix [4]嘧啶的合成，拆分，结构和外消旋作用：构象迁移率的定量

  摘要：

  报道了固有手性的1,3-交替的氮杂杯[4]嘧啶大环的合成，拆分，结构和外消旋化。用NBS，NCS和NFSI对单卤素取代的azacalix [4]嘧啶进行位点选择性卤化，产生了许多下边缘二卤代的1，3-交替azacalix [4] pyrimidines。带有两个近端取代基的1,3-交替的氮杂杯[4]嘧啶为AABB型和ABCC型固有手性大环，并通过消旋样品的拆分得到三对构象稳定的P和M对映体，其ee均> 99.5％。手性HPLC。绝对构型是通过X射线晶体学测定的，并与它们的CD光谱相关。测量了大环外消旋化的速率常数，并计算了焓（Δħ ⧧）和熵（Δ小号⧧活化的）由艾林情节方法测定。本研究表明，在下部边缘，两个大于范德华半径r w = 1.75Å（例如氯）和r w = 1.47Å（例如氟）的近端取代基的组合是该化合物的最低空间要求。分离和分离1,3-交替氮杂杂杯[4]嘧啶的构象稳定的固有手性对映

  DOI：

  10.1021/jo500054v

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.
• Synthesis, Resolution, Structure, and Racemization of Inherently Chiral 1,3-Alternate Azacalix[4]pyrimidines: Quantification of Conformation Mobility
  作者：Jiang-Tao Li、Li-Xia Wang、De-Xian Wang、Liang Zhao、Mei-Xiang Wang

  DOI：10.1021/jo500054v

  日期：2014.3.7

  macrocycles, and three pairs of conformationally stable P and M enantiomers with >99.5% ee were obtained from the resolution of racemic samples by chiral HPLC. Absolute configurations were determined by X-ray crystallography and were correlated with their CD spectra. The rate constants for racemization of macrocycles were measured, and enthalpies (ΔH⧧) and entropies (ΔS⧧) of activation were determined by the

  报道了固有手性的1,3-交替的氮杂杯[4]嘧啶大环的合成，拆分，结构和外消旋化。用NBS，NCS和NFSI对单卤素取代的azacalix [4]嘧啶进行位点选择性卤化，产生了许多下边缘二卤代的1，3-交替azacalix [4] pyrimidines。带有两个近端取代基的1,3-交替的氮杂杯[4]嘧啶为AABB型和ABCC型固有手性大环，并通过消旋样品的拆分得到三对构象稳定的P和M对映体，其ee均> 99.5％。手性HPLC。绝对构型是通过X射线晶体学测定的，并与它们的CD光谱相关。测量了大环外消旋化的速率常数，并计算了焓（Δħ ⧧）和熵（Δ小号⧧活化的）由艾林情节方法测定。本研究表明，在下部边缘，两个大于范德华半径r w = 1.75Å（例如氯）和r w = 1.47Å（例如氟）的近端取代基的组合是该化合物的最低空间要求。分离和分离1,3-交替氮杂杂杯[4]嘧啶的构象稳定的固有手性对映