6,13,20-Trihexadecoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarbaldehyde | 1028854-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6,13,20-Trihexadecoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarbaldehyde
• 英文别名: 6,13,20-trihexadecoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarbaldehyde
• CAS: 1028854-91-2；1033293-34-3
• 化学式: C₇₂H₁₁₄O₆
• 分子量: 1075.69
• InChiKey: WPVKHZMAOUVDBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.3
• 重原子数：
  78
• 可旋转键数：
  51
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,13,20-Trihexadecoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarbaldehyde 、 (1R,2R)-1,2-diaminocyclohexane 在 4 A molecular sieve 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以92%的产率得到
  参考文献：
  名称：

  Edge-Directed Dynamic Covalent Synthesis of a Chiral Nanocube

  摘要：

  The dynamic multicomponent syntheses of nanometer-sized chiral molecular cubes 1a and 1b from 8 tritopic 90 degrees corner units and 12 linear spacers using an edge-directed approach is described. Thus, the TFA-catalyzed reaction of 8 equiv C3- trihexadecycloxy-triformylcyclotribenzylene 2 as corner unit with 12 equiv of 1,4-phenylenediamine 3a or benzidine 3b as spacers yields nanocubes 1a and 1b, respectively in close to quantitative yield. The same reactions carried out with enantiomerically pure (P)-2(> 99% ee) gave the homochiral cubes (all-P)-1a and (all-P)-1b. Force field calculations predict an edge length of 17 angstrom and 21 angstrom for 1a and 1b, which is consistent with their dimensions estimated from DOSY experiments. Furthermore, the asymmetric syntheses of (P)-2 through dynamic thermodynamic resolution is described. This approach is based on the TFA-catalyzed reaction of racemic 2 with (R,R)-1,2-diaminocyclohexane (R)-5, which leads to a chiral cryptophane (> 90% yield) that is built-up from two (P)-2 linked together with three diamines (R)-5. Hydrolysis of this cryptophane provides (P)-2 with > 99% ee.

  DOI：

  10.1021/ja800803c
• 作为产物：
  描述：

  在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到6,13,20-Trihexadecoxytetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-tricarbaldehyde
  参考文献：
  名称：

  Edge-Directed Dynamic Covalent Synthesis of a Chiral Nanocube

  摘要：

  The dynamic multicomponent syntheses of nanometer-sized chiral molecular cubes 1a and 1b from 8 tritopic 90 degrees corner units and 12 linear spacers using an edge-directed approach is described. Thus, the TFA-catalyzed reaction of 8 equiv C3- trihexadecycloxy-triformylcyclotribenzylene 2 as corner unit with 12 equiv of 1,4-phenylenediamine 3a or benzidine 3b as spacers yields nanocubes 1a and 1b, respectively in close to quantitative yield. The same reactions carried out with enantiomerically pure (P)-2(> 99% ee) gave the homochiral cubes (all-P)-1a and (all-P)-1b. Force field calculations predict an edge length of 17 angstrom and 21 angstrom for 1a and 1b, which is consistent with their dimensions estimated from DOSY experiments. Furthermore, the asymmetric syntheses of (P)-2 through dynamic thermodynamic resolution is described. This approach is based on the TFA-catalyzed reaction of racemic 2 with (R,R)-1,2-diaminocyclohexane (R)-5, which leads to a chiral cryptophane (> 90% yield) that is built-up from two (P)-2 linked together with three diamines (R)-5. Hydrolysis of this cryptophane provides (P)-2 with > 99% ee.

  DOI：

  10.1021/ja800803c

文献信息

• Edge-Directed Dynamic Covalent Synthesis of a Chiral Nanocube
  作者：Di Xu、Ralf Warmuth

  DOI：10.1021/ja800803c

  日期：2008.6.18

  The dynamic multicomponent syntheses of nanometer-sized chiral molecular cubes 1a and 1b from 8 tritopic 90 degrees corner units and 12 linear spacers using an edge-directed approach is described. Thus, the TFA-catalyzed reaction of 8 equiv C3- trihexadecycloxy-triformylcyclotribenzylene 2 as corner unit with 12 equiv of 1,4-phenylenediamine 3a or benzidine 3b as spacers yields nanocubes 1a and 1b, respectively in close to quantitative yield. The same reactions carried out with enantiomerically pure (P)-2(> 99% ee) gave the homochiral cubes (all-P)-1a and (all-P)-1b. Force field calculations predict an edge length of 17 angstrom and 21 angstrom for 1a and 1b, which is consistent with their dimensions estimated from DOSY experiments. Furthermore, the asymmetric syntheses of (P)-2 through dynamic thermodynamic resolution is described. This approach is based on the TFA-catalyzed reaction of racemic 2 with (R,R)-1,2-diaminocyclohexane (R)-5, which leads to a chiral cryptophane (> 90% yield) that is built-up from two (P)-2 linked together with three diamines (R)-5. Hydrolysis of this cryptophane provides (P)-2 with > 99% ee.