3-amino-3-(4-pyridinyl)propionitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-amino-3-(4-pyridinyl)propionitrile
• 英文别名: 3-Amino-3-pyridin-4-ylpropanenitrile
• 化学式: C₈H₉N₃
• mdl: MFCD18652131
• 分子量: 147.18
• InChiKey: WUJVZPCXGXFWJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-3-(4-pyridinyl)propionitrile 在 溶剂黄146 作用下， 反应 120.0h， 生成
  参考文献：
  名称：

  A Robust Binary Supramolecular Organic Framework (SOF) with High CO₂ Adsorption and Selectivity

  摘要：

  A robust binary hydrogen-bonded supramolecular organic framework (SOF-7) has been synthesized by solvothermal reaction of 1,4-bis-(4-(3,5-dicyano-2,6-dipyridyl)dihydropyridyl)benzene (1) and 5,5'-bis-(azanediyl)-oxalyl-diisophthalic acid (2). Single crystal X-ray diffraction analysis shows that SOF-7 comprises 2 and 1,4-bis-(4-(3,5-dicyano-2,6-dipyridyl)pyridyl)benzene (3); the latter formed in situ from the oxidative dehydrogenation of 1. SOF-7 shows a three-dimensional four-fold interpenetrated structure with complementary O-H···N hydrogen bonds to form channels that are decorated with cyano and amide groups. SOF-7 exhibits excellent thermal stability and solvent and moisture durability as well as permanent porosity. The activated desolvated material SOF-7a shows high CO2 adsorption capacity and selectivity compared with other porous organic materials assembled solely through hydrogen bonding.

  DOI：

  10.1021/ja506577g
• 作为产物：
  描述：

  4-氰基吡啶 在 potassium tert-butylate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 3-amino-3-(4-pyridinyl)propionitrile
  参考文献：
  名称：

  Control of Assembly of Dihydropyridyl and Pyridyl Molecules via Directed Hydrogen Bonding

  摘要：

  两种二氢吡啶分子的结晶，即 1,4-双(4-(3,5-二氰基-2,6-二吡啶基)二氢吡啶)苯（[C40H24N10]-2DMF，1-2DMF；DMF=二甲基甲酰胺）和 1,4-双(4-(3,5-二氰基-2,6-二吡啶基)二氢吡啶基)苯（[C46H28N10]-2DMF，3-2DMF），以及它们各自的氧化吡啶类似物 1,4-双(4-(3、2）和 1,4-双(4-(3,5-二氰基-2,6-二吡啶基)吡啶基)苯基苯（[C46H24N10]-DMF，4-DMF）。二氢吡啶分子在溶液中通过原位氧化脱氢转化为吡啶产物。四种分子的结构已通过单晶和粉末 X 射线衍射得到了全面表征。由于母分子 1 和 3 两端的二氢吡啶环分别发生芳香化作用，氧化后的吡啶产物 2 和 4 更加细长。由于两个电子氧化结构体中失去了主要的 N-H 氢键供体，因此吡啶分子的固态超分子结构与二氢吡啶分子不同，它们是通过氢键进行分层组装的。总体而言，几何长度较短的分子 1 和分子 3 显示出紧密堆积的结构，而较长的分子 2 和分子 4 则组装成更为开放的超分子体系。

  DOI：

  10.1021/acs.cgd.5b00395

文献信息

• Polycatenated 2D Hydrogen-Bonded Binary Supramolecular Organic Frameworks (SOFs) with Enhanced Gas Adsorption and Selectivity
  作者：Jian Lü、Cristina Perez-Krap、Fabien Trousselet、Yong Yan、Nada H. Alsmail、Bahar Karadeniz、Nicholas M. Jacques、William Lewis、Alexander J. Blake、François-Xavier Coudert、Rong Cao、Martin Schröder

  DOI：10.1021/acs.cgd.8b00153

  日期：2018.4.4

  acid (4; to form SOF-9), or 5,5'-bis-(azanediyl)-oxalyl-diisophthalic acid (5; to form SOF-10). Complementary O-H···N hydrogen bonds assemble 2D 63-hcb (honeycomb) subunits that pack as layers in SOF-8 to give a three-dimensional (3D) supramolecular network with parallel channels hosting guest DMF (DMF = N,N'-dimethylformamide) molecules. SOF-9 and SOF-10 feature supramolecular networks of 2D → 3D inclined

  二维（2D）超分子有机框架（SOF）的受控组装已通过二元策略证明，其中1,4-双-（4-（3,5-二氰基-2,6-二吡啶基）吡啶基）萘（由1,4-双-（4-（3,5-二氰基-2,6-二吡啶基）二氢吡啶基）萘（1）的氧化脱氢原位生成的2）与三联苯基- 3,3'，4,4'-四羧酸（3;形成SOF-8），5,5'-（蒽-9,10-二基）二间苯二甲酸（4;形成SOF-9）或5 ，5′-双-（氮杂二基）-草酰基-二间苯二甲酸（5；形成SOF-10）。互补的OH···N氢键组装2D 63-hcb（蜂窝）亚基，这些亚基作为SOF-8中的层堆积，从而形成三维（3D）超分子网络，并带有承载客体DMF的平行通道（DMF = N，N'-二甲基甲酰胺）分子。SOF-9和SOF-10具有与SOF-8类似的hcb层的2D→3D倾斜聚级超分子网络。尽管SOF-8会在去除客体后发生骨架塌陷，但是SOF-9和SOF-10的
• A Robust Binary Supramolecular Organic Framework (SOF) with High CO₂ Adsorption and Selectivity
  作者：Jian Lü、Cristina Perez-Krap、Mikhail Suyetin、Nada H. Alsmail、Yong Yan、Sihai Yang、William Lewis、Elena Bichoutskaia、Chiu C. Tang、Alexander J. Blake、Rong Cao、Martin Schröder

  DOI：10.1021/ja506577g

  日期：2014.9.17

  A robust binary hydrogen-bonded supramolecular organic framework (SOF-7) has been synthesized by solvothermal reaction of 1,4-bis-(4-(3,5-dicyano-2,6-dipyridyl)dihydropyridyl)benzene (1) and 5,5'-bis-(azanediyl)-oxalyl-diisophthalic acid (2). Single crystal X-ray diffraction analysis shows that SOF-7 comprises 2 and 1,4-bis-(4-(3,5-dicyano-2,6-dipyridyl)pyridyl)benzene (3); the latter formed in situ from the oxidative dehydrogenation of 1. SOF-7 shows a three-dimensional four-fold interpenetrated structure with complementary O-H···N hydrogen bonds to form channels that are decorated with cyano and amide groups. SOF-7 exhibits excellent thermal stability and solvent and moisture durability as well as permanent porosity. The activated desolvated material SOF-7a shows high CO2 adsorption capacity and selectivity compared with other porous organic materials assembled solely through hydrogen bonding.
• Control of Assembly of Dihydropyridyl and Pyridyl Molecules via Directed Hydrogen Bonding
  作者：Jian Lü、Li-Wei Han、Nada H. Alsmail、Alexander J. Blake、William Lewis、Rong Cao、Martin Schröder

  DOI：10.1021/acs.cgd.5b00395

  日期：2015.9.2

  The crystallization of two dihydropyridyl molecules, 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)dihydropyridyl)benzene ([C40H24N10]·2DMF, 1·2DMF; DMF = dimethylformamide) and 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)dihydropyridyl)phenylbenzene ([C46H28N10]·2DMF, 3·2DMF), and their respective oxidized pyridyl analogues, 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)pyridyl)benzene ([C40H20N10], 2) and 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)pyridyl)phenylbenzene ([C46H24N10]·DMF, 4·DMF), has been achieved under solvothermal conditions. The dihydropyridyl molecules are converted to their pyridyl products via in situ oxidative dehydrogenation in solution. The structures of the four molecules have been fully characterized by single crystal and powder X-ray diffraction. The oxidized pyridyl products, 2 and 4, are more elongated due to aromatization of the dihydropyridyl rings at each end of their parent molecules 1 and 3, respectively. The solid-state supramolecular structures of the pyridyl molecules are distinct from the dihydropyridyl molecules in terms of their hierarchical assembly via hydrogen bonding due to the loss of primary N–H hydrogen bond donors in the two electron oxidized tectons. Overall, the geometrically shorter molecules 1 and 3 display close-packed structures, whereas the more extended 2 and 4 assemble into more open supramolecular systems.

  两种二氢吡啶分子的结晶，即 1,4-双(4-(3,5-二氰基-2,6-二吡啶基)二氢吡啶)苯（[C40H24N10]-2DMF，1-2DMF；DMF=二甲基甲酰胺）和 1,4-双(4-(3,5-二氰基-2,6-二吡啶基)二氢吡啶基)苯（[C46H28N10]-2DMF，3-2DMF），以及它们各自的氧化吡啶类似物 1,4-双(4-(3、2）和 1,4-双(4-(3,5-二氰基-2,6-二吡啶基)吡啶基)苯基苯（[C46H24N10]-DMF，4-DMF）。二氢吡啶分子在溶液中通过原位氧化脱氢转化为吡啶产物。四种分子的结构已通过单晶和粉末 X 射线衍射得到了全面表征。由于母分子 1 和 3 两端的二氢吡啶环分别发生芳香化作用，氧化后的吡啶产物 2 和 4 更加细长。由于两个电子氧化结构体中失去了主要的 N-H 氢键供体，因此吡啶分子的固态超分子结构与二氢吡啶分子不同，它们是通过氢键进行分层组装的。总体而言，几何长度较短的分子 1 和分子 3 显示出紧密堆积的结构，而较长的分子 2 和分子 4 则组装成更为开放的超分子体系。