(+/-)-2,7,12-trihydroxy-3,8,13-triiodo-10,15-dihydro-5H-tribenzocyclononene | 168751-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (+/-)-2,7,12-trihydroxy-3,8,13-triiodo-10,15-dihydro-5H-tribenzocyclononene
• 英文别名: 6,13,20-triiodotetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene-5,12,19-triol
• CAS: 168751-92-6
• 化学式: C₂₁H₁₅I₃O₃
• 分子量: 696.062
• InChiKey: XFTXZRNGJMVILK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2,7,12-trihydroxy-3,8,13-triiodo-10,15-dihydro-5H-tribenzocyclononene 、 溴代十六烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以57.3%的产率得到2,7,12-tris(hexadecyloxy)-3,8,13-triiodo-10,15-dihydro-5H-tribenzo[a,d,g][9]annulene
  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：

  M-(+)-2,7,12-trihydroxy-3,8,13-triiodo-10,15-dihydro-5H-tribenzocyclononene 以 1,4-二氧六环 为溶剂， 生成 (+/-)-2,7,12-trihydroxy-3,8,13-triiodo-10,15-dihydro-5H-tribenzocyclononene
  参考文献：
  名称：

  Garcia, Chantal; Collet, Andre, Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 52 - 58

  摘要：

  DOI：