1,8,10,17-tetraazapentacyclo[8.8.1.1^8,17.0^2,7.0^11,16]icosane | 57211-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪烷类
• 英文名称: 1,8,10,17-tetraazapentacyclo[8.8.1.1^8,17.0^2,7.0^11,16]icosane
• 英文别名: (2R,7R,11S,16S)-1,8,10,17-tetraazapentacyclo[8.8.1.1(8,17).0(2,7).0(11,16)]icosane；1,3,5,7-tetraazapentacyclo[3.3.2.4^9,10.4^11,12]eicosane；(2r,7r,11s,16s)-1,8,10,17-Tetrazapentacyclo [8.8.1.18,17.02,7.011,16]icosane；(2R,7R,11S,16S)-1,8,10,17-tetrazapentacyclo[8.8.1.18,17.02,7.011,16]icosane
• CAS: 57211-44-6
• 化学式: C₁₆H₂₈N₄
• 分子量: 276.425
• InChiKey: FIDIPBYMFPVTCL-RUPPMWDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  13
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,8,10,17-tetraazapentacyclo[8.8.1.1^8,17.0^2,7.0^11,16]icosane 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.25h， 以70%的产率得到(3aRS,7aRS)-1,3-dinitrosooctahydro-1H-benzimidazole
  参考文献：
  名称：

  The disordered molecular structure of (3aRS,7aRS)-1,3-dinitrosooctahydro-1H-benzimidazole

  摘要：

  The title compound, C(7)H(12)N(4)O(2), was obtained by nitrosation of the aminal cage (2R,7R,11S,16S)-1,8,10,17-tetraazapenta-cyclo[8.8.1.1(8,17).0(2,7).0(11,16)]icosane. The crystal structure is a racemic mixture of RR and SS enantiomers. The asymmetric unit contains two crystallographically independent half-molecules, one having two partially occupied conformers with refined occupancy factors of 0.747 (3) and 0.253 (3). The molecules sit across twofold axes. The unique molecules each form chains parallel to [001], with molecules connected by intermolecular C-H center dot center dot center dot O hydrogen bonds. The bonding between adjacent chains is weak. The analysis of eight different crystals confirmed the presence of disordered and nondisordered molecules in the same structure as a regular feature.

  DOI：

  10.1107/s0108270111046397
• 作为产物：
  描述：

  聚合甲醛 、 trans-1,2-Diaminocyclohexane 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 以87%的产率得到1,8,10,17-tetraazapentacyclo[8.8.1.1^8,17.0^2,7.0^11,16]icosane
  参考文献：
  名称：

  一系列的1- [2-芳基-1-二氮烯基] -3-（{3- [2-芳基-1-二氮烯基]全氢苯并[ d ]咪唑-1-基}甲基）全氢苯并[ d ]咪唑。合成与表征

  摘要：

  重氮盐与1,2-二氨基环己烷与甲醛混合的溶液反应，得到1- [2-芳基-1-二氮烯基] -3-（{3- [2-芳基-1-二氮烯基]全氢苯并[ d ]咪唑- 1-yl}甲基）过氢苯并-[ d ]咪唑（6），是一系列新的双三氮烯，其连接性不同于以前报道的任何类型的双三氮烯。产品主要通过NMR和IR光谱，元素分析进行​​表征，并通过X射线晶体学进行明确表征。全氢咪唑环的亚甲基质子为非对映异构体，在11 H NMR谱。但是，对NMR光谱的详细分析表明，存在多于一组的双峰信号，这表明存在不同的旋转异构体形式的产物。的13 C NMR谱的分配，通过用选择的化合物的COSY和DEPT实验协助。

  DOI：

  10.1002/jhet.5570430134

文献信息

• A new approach to enantiomerically pure bis-imidazoles derived from trans-1,2-diaminocyclohexane
  作者：Paulina Mucha、Grzegorz Mlostoń、Marcin Jasiński、Anthony Linden、Heinz Heimgartner

  DOI：10.1016/j.tetasy.2008.06.015

  日期：2008.7

  Racemic as well as enantiomerically pure trans-1,1′-(cyclohexane-1,2-diyl)bis(imidazole N-oxides) were prepared from trans-cyclohexane-1,2-bis(methylidenamine) and 1,2-dione monooximes (α-hydroxyiminoketones). The enantiomeric purity of selected products was determined by means of 1H NMR spectroscopy in the presence of (+)-(R)-(tert-butyl)(phenyl)phosphonothioic acid as a chiral solvating agent. Deoxygenation

  由反式-环己烷-1,2-双（甲亚胺）和1,2-二酮制备外消旋及对映体纯的反式-1,1'-（环己烷-1,2-二基）双（咪唑N-氧化物）一肟（α-羟基亚氨基酮）。在（+）-（R）-（叔丁基）（苯基）膦硫酸作为手性溶剂的存在下，通过1 H NMR光谱法测定所选产物的对映体纯度。用阮内镍处理脱氧得到相应的手性双咪唑。
• New cyclic aminals derived from rac-trans-1,2-diaminocyclohexane: synthesis and crystal structure of racemic 1,8,10,12-tetraazatetracyclo[8.3.1.1.8,1202,7] pentadecane and a route to its enantiomerically pure (R,R) and (S,S) isomers
  作者：Augusto Rivera、Diego Quiroga、Leonardo Jiménez-Cruz、Karla Fejfarová、Michal Dušek

  DOI：10.1016/j.tetlet.2011.11.046

  日期：2012.1

  New enantiomerically pure macrocyclic aminals (2R,7R)- and (2S,7S)-1,8,10,12-tetraazatetracyclo[8.3.1.1.8,1202,7]pentadecane (4a and 4b) were obtained by a three component reaction between their respective pure enantiomer of trans-1,2-diaminocyclohexane, ammonia, and formaldehyde. Additionally, the X-ray structure of the racemic compound 4 and the specific rotations of the racemic and optically pure

  新的对映体纯大环缩醛（2 R，7 R）-和（2 S，7 S）-1,8,10,12-四氮杂四环[8.3.1.1。8,12 0 2,7 ]十五烷（图4a和图4b），通过它们各自的纯对映体之间的三个组分反应获得的反式-1,2-二氨基环己烷，氨和甲醛。另外，测定外消旋化合物4的X射线结构以及外消旋和光学纯化合物的比旋光度。为了进一步理解对映异构体4a和4b的合成效用，曼尼希型反应与1进行H-苯并三唑，得到（3a R，7a R）-和（3a S，7a S）-1,1'-[2,3,3a，4,5,6,7,7a-octahydro-1 H -1,3-苯并咪唑-1,3-二基]双（亚甲基）}双-1 H-苯并三唑（9和10），并为制备用于不对称催化的手性配体提供了新的可能性。
• Cage peroxides having planar bridgehead nitrogen atoms
  作者：John T. Edward、Francis L. Chubb、Denis F.R. Gilson、Rosemary C. Hynes、Françoise Sauriol、Alain Wiesenthal

  DOI：10.1139/cjc-77-5-6-1057

  日期：——

  Three new cage peroxides, 1,6-diaza-3,4,8,9-tetraoxabicyclo[4.4.2]dodecane (3a),1,6-diaza-3,4,8,9-tetraoxa-11-methylbicyclo[4.4.2]dodecane (3b), and 1,6-diaza-3,4,8,9-tetraoxatricyclo[4.4.2.4(11,12)]hexadecane (4), have been prepared by reaction of 1,2-diaminoethane, 1,2-diaminopropane, and trans-1,2-diaminocyclohexane, respectively, with formaldehyde and hydrogen peroxide in aqueous acidic solution. Their structures have been established by X-ray diffraction, and show the bridgehead nitrogen atoms to be predominantly sp(2) hybridized. The structures accord with H-1 and C-13 NMR spectra. Variable temperature NMR studies show that the diperoxide 3a begins to undergo rapid inversion (on the NMR time scale) at about 303 K; up to 370 K the diperoxides 3b and 4 show no conformational change.