2,6,10-tris-12c-methyl-4,8,12-trioxatricornan | 164933-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6,10-tris-12c-methyl-4,8,12-trioxatricornan
• 英文别名: N-(2-aminoethyl)-N-[11,17-bis[2-aminoethyl-(4-methylphenyl)sulfonylamino]-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(20),16,18-nonaen-5-yl]-4-methylbenzenesulfonamide
• CAS: 164933-50-0
• 化学式: C₄₇H₄₈N₆O₉S₃
• 分子量: 937.131
• InChiKey: JDHNUPIMNMNALL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  65.0
• 可旋转键数：
  15.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  217.89
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3-bis(benzyloxy)benzoyl chloride 、 2,6,10-tris-12c-methyl-4,8,12-trioxatricornan 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以67%的产率得到
  参考文献：
  名称：

  Synthesis of metallomacrocyclophanes: Deduction of structure from electrospray ionization mass spectroscopy and molecular mechanics computations

  摘要：

  The synthesis of metallomacrocyclophanes 7-tos and 8, in which environmentally tunable ferric-catecholamide coordination bonds hold the cyclophane together, is described. W-vis spectroscopic studies of 7-tos and 8 display characteristics of ferric-tris(catecholamide) complexes, i.e. burgundy color (lambda(max) = ca. 490 nm)and high stability, at high pH, and 1:1 stoichiometry. Electrospray ionization mass spectra of 8 show prominent ions due to a monomeric 1:1 (ligand/metal) complex. Molecular mechanics calculations on 7 and 8 indicate that oar-isomeric configurations predominate, leaving a void in the metallomacrocyclophane interiors.

  DOI：

  10.1016/0040-4020(95)00287-i
• 作为产物：
  描述：

  2,6,10-tris-12c-methyl-4,8,12-trioxatricornan 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以90%的产率得到2,6,10-tris-12c-methyl-4,8,12-trioxatricornan
  参考文献：
  名称：

  Synthesis of metallomacrocyclophanes: Deduction of structure from electrospray ionization mass spectroscopy and molecular mechanics computations

  摘要：

  The synthesis of metallomacrocyclophanes 7-tos and 8, in which environmentally tunable ferric-catecholamide coordination bonds hold the cyclophane together, is described. W-vis spectroscopic studies of 7-tos and 8 display characteristics of ferric-tris(catecholamide) complexes, i.e. burgundy color (lambda(max) = ca. 490 nm)and high stability, at high pH, and 1:1 stoichiometry. Electrospray ionization mass spectra of 8 show prominent ions due to a monomeric 1:1 (ligand/metal) complex. Molecular mechanics calculations on 7 and 8 indicate that oar-isomeric configurations predominate, leaving a void in the metallomacrocyclophane interiors.

  DOI：

  10.1016/0040-4020(95)00287-i

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.