(2R,3R,16R,17R,30R,31R)-(1,4,15,18,29,32)-hexaza(2,3:16,17:30,31)-tributano(7,21,40)-triphenoxy(6,9:10,13 20,23:24,27:34,37:38,41)hexaetheno(2H,3H,16H,17H,30H,31H)hexahydro[42]annulene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,16R,17R,30R,31R)-(1,4,15,18,29,32)-hexaza(2,3:16,17:30,31)-tributano(7,21,40)-triphenoxy(6,9:10,13 20,23:24,27:34,37:38,41)hexaetheno(2H,3H,16H,17H,30H,31H)hexahydro[42]annulene
• 英文别名: (8R,13R,26R,31R,44R,49R)-4,17,35-triphenoxy-7,14,25,32,43,50-hexazadecacyclo[50.2.2.22,5.216,19.220,23.234,37.238,41.08,13.026,31.044,49]hexahexaconta-1(55),2,4,6,14,16,18,20,22,24,32,34,36,38(58),39,41(57),42,50,52(56),53,59,61,63,65-tetracosaene
• 化学式: C₇₈H₇₂N₆O₃
• 分子量: 1141.47
• InChiKey: AOMJVGKDOYFCJG-HDUFXPENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  87
• 可旋转键数：
  6
• 环数：
  19.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,16R,17R,30R,31R)-(1,4,15,18,29,32)-hexaza(2,3:16,17:30,31)-tributano(7,21,40)-triphenoxy(6,9:10,13 20,23:24,27:34,37:38,41)hexaetheno(2H,3H,16H,17H,30H,31H)hexahydro[42]annulene 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以98%的产率得到(2R,3R,16R,17R,30R,31R)-(1,4,15,18,29,32)-hexaza(2,3 : 16,17 : 30,31)-tributano-(7,21,40)-tri-(2,2-dimethoxy-N-methylethanamino)-(6,9:10,13:20,23:24,27:34,37:38,41)hexaetheno(1H, 2H,3H,4H,5H,14H,15H,16H,17H,18H,19H,28H,29H,30H,31H,32H,33H,42H)octadecahydro[42]annulene
  参考文献：
  名称：

  Synthesis of tri-substituted biaryl based trianglimines: formation of C3-symmetrical and non-symmetrical regioisomers

  摘要：

  通过 4-溴-2-氟苯甲醛与不同的仲胺和苯酚反应，合成了 2-官能化的芳香族一醛，收率从良好到极佳。新官能化的芳香族一醛与 4-甲酰基苯硼酸发生铃木偶联反应，得到相应的 2-官能化-4,4′-联苯二醛，收率良好（47-85%）。2-官能化-4,4′-联苯二醛与(1R,2R)-1,2-二氨基环己烷的[3+3]-环缩合反应生成了 C3-对称和非对称三醯亚胺异构体混合物。在 THF 和 MeOH 的混合物中用 NaBH4 还原 C3 对称和非对称三醯亚胺，可以高产率得到相应的三醯胺。

  DOI：

  10.1039/c0ob00944j
• 作为产物：
  描述：

  4-溴-2-氟苯甲醛 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 56.0h， 生成 (2R,3R,16R,17R,30R,31R)-(1,4,15,18,29,32)-hexaza(2,3:16,17:30,31)-tributano(7,21,40)-triphenoxy(6,9:10,13 20,23:24,27:34,37:38,41)hexaetheno(2H,3H,16H,17H,30H,31H)hexahydro[42]annulene 、 (2R,3R,16R,17R,30R,31R)-(1,4,15,18,29,32)-hexaza(2,3:16,17:30,31)-tributano-(7,21,35)-triphenoxy(6,9:10,13:20,23:24,27:34,37:38,41)hexaetheno(2H,3H,16H,17H,30H,31H)hexahydro[42]annulene
  参考文献：
  名称：

  Synthesis of tri-substituted biaryl based trianglimines: formation of C3-symmetrical and non-symmetrical regioisomers

  摘要：

  通过 4-溴-2-氟苯甲醛与不同的仲胺和苯酚反应，合成了 2-官能化的芳香族一醛，收率从良好到极佳。新官能化的芳香族一醛与 4-甲酰基苯硼酸发生铃木偶联反应，得到相应的 2-官能化-4,4′-联苯二醛，收率良好（47-85%）。2-官能化-4,4′-联苯二醛与(1R,2R)-1,2-二氨基环己烷的[3+3]-环缩合反应生成了 C3-对称和非对称三醯亚胺异构体混合物。在 THF 和 MeOH 的混合物中用 NaBH4 还原 C3 对称和非对称三醯亚胺，可以高产率得到相应的三醯胺。

  DOI：

  10.1039/c0ob00944j

文献信息

• Probing the mechanism and dynamic reversibility of trianglimine formation using real-time electrospray ionization time-of-flight mass spectrometry
  作者：Hany F. Nour、Ana M. Lopez-Periago、Nikolai Kuhnert

  DOI：10.1002/rcm.6203

  日期：2012.5.15

  The [3+3]‐cyclocondensation reactions of chiral (1R,2R)‐1,2‐diaminocyclohexane with aromatic or aliphatic bis‐aldehydes to form trianglimine macrocycles were reported a decade ago and were believed to proceed through a stepwise mechanistic pathway; however, no intermediates were ever isolated or detected and characterized.

  十年前已经报道了手性（1 R，2 R）-1，2-二氨基环己烷与芳族或脂肪族双醛形成三anglimine大环的[3 + 3]-环缩合反应，并认为这是通过逐步的机理途径进行的; 但是，从未分离或检测到任何中间体并进行了表征。
• Synthesis of tri-substituted biaryl based trianglimines: formation of C3-symmetrical and non-symmetrical regioisomers
  作者：Hany F. Nour、Marius F. Matei、Bassem S. Bassil、Ulrich Kortz、Nikolai Kuhnert

  DOI：10.1039/c0ob00944j

  日期：——

  2-Functionalised aromatic monoaldehydes were synthesised in good to excellent yields by reacting 4-bromo-2-fluorobenzaldehyde with different secondary amines and phenol. The Suzuki-coupling reaction of the newly functionalised aromatic monoaldehydes with 4-formylphenylboronic acid afforded the corresponding 2-functionalised-4,4′-biphenyldialdehydes in good yields (47–85%). The [3+3]-cyclocondensation reactions of the 2-functionalised-4,4′-biphenyldialdehydes with (1R,2R)-1,2-diaminocyclohexane afforded a mixture of regioisomeric C3-symmetrical and non-symmetrical trianglimines. Reduction of the C3-symmetrical and the non-symmetrical trianglimines with NaBH4 in a mixture of THF and MeOH afforded the corresponding trianglamines in high yields.

  通过 4-溴-2-氟苯甲醛与不同的仲胺和苯酚反应，合成了 2-官能化的芳香族一醛，收率从良好到极佳。新官能化的芳香族一醛与 4-甲酰基苯硼酸发生铃木偶联反应，得到相应的 2-官能化-4,4′-联苯二醛，收率良好（47-85%）。2-官能化-4,4′-联苯二醛与(1R,2R)-1,2-二氨基环己烷的[3+3]-环缩合反应生成了 C3-对称和非对称三醯亚胺异构体混合物。在 THF 和 MeOH 的混合物中用 NaBH4 还原 C3 对称和非对称三醯亚胺，可以高产率得到相应的三醯胺。