2,6-diamino-12c-methyl-4,8,12-trioxatricornan | 138259-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,6-diamino-12c-methyl-4,8,12-trioxatricornan
• 英文别名: 12c-Methyl-12cH-4,8,12-trioxadibenzo[cd,mn]pyrene-2,6-diamine；1-methyl-8,14,22-trioxahexacyclo[11.7.1.13,19.02,7.09,21.015,20]docosa-2,4,6,9,11,13(21),15,17,19-nonaene-5,11-diamine
• CAS: 138259-66-2
• 化学式: C₂₀H₁₄N₂O₃
• 分子量: 330.343
• InChiKey: BCTNDZQXDUOJQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  79.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,8,12-trioxa-4,8,12,12c-tetrahydrodibenzopyrenylium tetrafluoroborate 在 正丁基锂 、 三甲基氯硅烷 、 氨 、 溴 、 sodium amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 20.0h， 生成 2,6-diamino-12c-methyl-4,8,12-trioxatricornan
  参考文献：
  名称：

  Synthesis of trioxatricornan and derivatives. Useful keystones for the construction of rigid molecular cavities

  摘要：

  The synthesis of a new class of organic keystones for the development of macrocage structures is presented. These represent some of the most versatile building blocks for macrocage construction. The keystone structure developed herein can be interpreted as either a centrally alkylated [cd,mn]dibenzopyrene or a tris ortho-bridged triphenylmethane. We call this basic skeleton tricornan. Routes into both chiral (C3 and C1 symmetry) and achiral (C3-upsilon symmetry) derivatives are reported. The synthesis of derivatives of the trioxatricornan keystone, leading to two macrocage structures, is presented. The X-ray structures of cent-methyltrioxatricornan 7 and 2,6,10-tris(dimethylamino)-cent-methyltrioxatricornan (20) are discussed and compared to that of 1,1,1-triphenylethane. Empirical force field and AM1 calculations are compared to the X-ray structures and discussed. A general discussion on the keystone analogy is presented.

  DOI：

  10.1021/jo00027a015

文献信息

• Synthesis of trioxatricornan and derivatives. Useful keystones for the construction of rigid molecular cavities
  作者：Michael Lofthagen、Russell VernonClark、Kim K. Baldridge、Jay S. Siegel

  DOI：10.1021/jo00027a015

  日期：1992.1

  The synthesis of a new class of organic keystones for the development of macrocage structures is presented. These represent some of the most versatile building blocks for macrocage construction. The keystone structure developed herein can be interpreted as either a centrally alkylated [cd,mn]dibenzopyrene or a tris ortho-bridged triphenylmethane. We call this basic skeleton tricornan. Routes into both chiral (C3 and C1 symmetry) and achiral (C3-upsilon symmetry) derivatives are reported. The synthesis of derivatives of the trioxatricornan keystone, leading to two macrocage structures, is presented. The X-ray structures of cent-methyltrioxatricornan 7 and 2,6,10-tris(dimethylamino)-cent-methyltrioxatricornan (20) are discussed and compared to that of 1,1,1-triphenylethane. Empirical force field and AM1 calculations are compared to the X-ray structures and discussed. A general discussion on the keystone analogy is presented.