N-(9-anthrylmethylene)benzylamine | 14607-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(9-anthrylmethylene)benzylamine
• 英文别名: 1-(anthracen-9-yl)-N-benzylmethanimine；N-[(1e)-9-anthrylmethylene]-N-benzylamine；1-anthracen-9-yl-N-benzylmethanimine
• CAS: 14607-11-5
• 化学式: C₂₂H₁₇N
• 分子量: 295.384
• InChiKey: SRPAVUMJGNILLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(9-anthrylmethylene)benzylamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以5.74 g的产率得到9-[(N-benzylamino)methyl]anthracene
  参考文献：
  名称：

  芳香冠醚与（9-蒽基）甲基铵衍生物的氢键配合物。超分子光化学和光物理学。pH 可控超分子开关†

  摘要：

  (9-蒽基)甲基铵和(9-蒽基)苄基铵四(六氟磷酸盐)盐在CH2Cl2中与含有二苯(DB)o的芳香冠醚形成氢键配合物。

  DOI：

  10.1021/ja9715760
• 作为产物：
  描述：

  9-蒽甲醛 、 苄胺 以 甲醇 为溶剂， 反应 24.0h， 生成 N-(9-anthrylmethylene)benzylamine
  参考文献：
  名称：

  分子相互作用，质子交换和包含过程和[2]假轮烷形成的光诱导过程

  摘要：

  主体和客体组分的适当设计允许形成新型的[2]假轮烷复合物，该复合物具有间断的光诱导电子转移（PET）-耦合的荧光共振能量转移（FRET）反应。这是使用基于NO 6的氮杂皇冠醚作为主体单元（H）的包合配合物的第一个例子。具有不同塞子大小的不同客体分子（G1，G2，G3和G4）用于研究。与G1，G2和G3不同，具有相对较大的塞子的G4不能形成[2]假轮烷复合物。等温滴定微量热法测量显示，随着塞子尺寸的变化，H·G1，H·G2和H·G3的缔合常数有系统的增加。热力学数据表明，H·G1 / H·G2 / H·G3的形成完全由大的正熵增益驱动（Ť Δ小号= 19.69 / 26.80 / 21.81千焦·摩尔-1），而焓变为H略高。负·G1 / H·G3（-2.61 / -1.97 KJ·摩尔-1）和轻微阳性·H·G2 （ΔH = 5.98 kJ·mol –1）。对于这三种包合物，观察到了PET偶联

  DOI：

  10.1021/jo400752d

文献信息

• Evaluating hydrogen bonding control in the diastereoselective Diels–Alder reactions of 9-(2-aminoethyl)-anthracene derivatives
  作者：R. A. Bawa、F.-M. Gautier、H. Adams、A. J. H. M. Meijer、S. Jones

  DOI：10.1039/c5ob01343g

  日期：——

  Hydrogen bonding can be used to control the stereoselectivity of the cycloaddition of some anthracene derivatives. DFT calculations provide support for the origins of the selectivity in these reactions.

  氢键可以用于控制某些蒽衍生物的环加成的立体选择性。DFT计算支持这些反应选择性的起源。
• BP23C7: high-yield synthesis and application in constructing [3]rotaxanes and responsive pseudo[2]rotaxanes
  作者：Manisha Prakashni、Suvankar Dasgupta

  DOI：10.1039/d3ob02094k

  日期：——

  BP23C7 forms pseudo[2]rotaxane with a dibenzylammonium ion (DBA+), exhibiting a good association constant value (ka = 1 × 103 M−1). Subsequently, fluorophoric properties of BP23C7 and anthracene terminated axles are blended to create responsive pseudo[2]rotaxanes. The “turn-on” fluorescence response of BP23C7 due to the addition of fluoride and chloride anions to pseudo[2]rotaxane systems has been investigated

  以市售起始原料合成联苯-23-冠-7 醚 (BP23C7)，收率 86%。 BP23C7与二苄基铵离子(DBA + )形成假[2]轮烷，表现出良好的缔合常数值( k a = 1 × 10 3 M -1 )。随后，将 BP23C7 和蒽封端轴的荧光特性混合以产生响应性假[2]轮烷。已经研究了由于向拟[2]轮烷系统中添加氟和氯阴离子而引起的 BP23C7 的“开启”荧光响应。由于离子对形成而引起的相应轴的蒽部分的伴随荧光猝灭已经得到解决。此外，[23]冠醚的两种变体，即BP23C7和邻二甲苯-23-冠-7醚(X23C7)，被应用于构建同[3]轮烷结构。由DBA +部分和末端烯烃组成的半轴分别与两种[23]冠醚混合，并使用格鲁布斯第一代催化剂进行自复分解。
• Intramolecular Diels-Alder additions. 1. Additions to anthracene and acridine
  作者：Engelbert Ciganek

  DOI：10.1021/jo01296a031

  日期：1980.4
• In(III) and Sc(III) based coordination polymers derived from rigid benzimidazole-5,6-dicarboxylic acid: Synthesis, crystal structure and catalytic property
  作者：Juan Chai、Pengcheng Wang、Jia Jia、Bing Ma、Jing Sun、Yufang Tao、Ping Zhang、Li Wang、Yong Fan

  DOI：10.1016/j.poly.2017.10.028

  日期：2018.2

  Two new coordination polymers (CPs), [InCl(H(2)bidc)(2)(H2O)](n) (1) and [Sc(Hbidc)(OH)(H2O)](n) (2) (H(3)bidc = benzimidazole-5,6-dicarboxylic acid) were synthesized through a solvothermal approach. 1 exhibits a 1D infinite chain, which further constructs a 3D supramolecular framework via hydrogen bonds. 2 features a 3D supramolecular framework consisting of left- and right-handed chiral layers, which contain the left- and right-handed chiral spiral chains. The adjacent layers stack through pi-pi stacking interactions between benzene and imidazole rings. 1 exhibits excellent catalytic reactivity for the Strecker reaction and can be recycled four consecutive reactions with more than 95% conversion yields. (C) 2017 Elsevier Ltd. All rights reserved.
• Polycyclic maleimide-based derivatives as first dual modulators of neuronal calcium channels and GSK-3β for Alzheimer's disease treatment
  作者：Alessandra Bisi、Raquel L. Arribas、Matteo Micucci、Roberta Budriesi、Alessandra Feoli、Sabrina Castellano、Federica Belluti、Silvia Gobbi、Cristobal de los Rios、Angela Rampa

  DOI：10.1016/j.ejmech.2018.12.003

  日期：2019.2

  Current healthcare has significantly increased the average life expectancy, leading to a consequently greater incidence of age-related diseases, such as Alzheimer's disease. Following a multitarget approach, in this paper a series of polycyclic maleimide-based derivatives were designed and synthesized aimed at simultaneously modulate neuronal calcium channels and glycogen synthase kinase 3-beta (GSK-3(3 beta), validated targets to combat Alzheimer' disease. Different structural modifications were performed on the polycyclic scaffold in order to investigate the structure-activity relationships and compound 10 emerged as a promising non-toxic lead compound, endowed with calcium modulating brain-addressed properties and significant GSK-3 beta inhibitory activity. Moreover, the easily affordable polycyclic core appears as a new appealing privileged structure in medicinal chemistry. (C) 2018 Elsevier Masson SAS. All rights reserved.