N-2,2'-bis(pyrazolyl)ethyl-N-benzylamine | 892862-26-9

• 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: N-2,2'-bis(pyrazolyl)ethyl-N-benzylamine
• 英文别名: N-benzyl-2,2-di(pyrazol-1-yl)ethanamine
• CAS: 892862-26-9
• 化学式: C₁₅H₁₇N₅
• 分子量: 267.333
• InChiKey: IAOYXMVEWHKLTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  双(三苯基膦)硝酸铜(I) 、 N-2,2'-bis(pyrazolyl)ethyl-N-benzylamine 以 not given 为溶剂， 生成 (N-2,2'-bis(pyrazolyl)ethyl-N-benzylamine)(triphenylphosphine)copper(I) nitrate
  参考文献：
  名称：

  New N,N,N-Heteroscorpionates Based on 2,2‘-Bis(pyrazolyl)ethanamine and Its Derivatives. Ligands Designed for Probing Supramolecular Interactions

  摘要：

  The successful design and synthesis of the new bis( pyrazolyl)ethanamine ligand and its copper( I) triphenylphosphine complex is reported. The ligand coordinates to the copper( I) center in a fac tridentate fashion, through both the pyrazolyl rings and the nitrogen atom from the NH2 group. In the solid state, the compound is organized in a 2D noncovalent network by N - H center dot center dot center dot pi and C - H center dot center dot center dot pi interactions and hydrogen bonds. The analogous ligand with a benzyl group substituted on the amine forms a complex with the same copper( I) center that has a similar 2D supramolecular structure and, in addition, is organized by the benzyl synthon into a 3D architecture.

  DOI：

  10.1021/ic060347o
• 作为产物：
  描述：

  2,2′-bis(pyrazolyl)-ethylamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以78%的产率得到N-2,2'-bis(pyrazolyl)ethyl-N-benzylamine
  参考文献：
  名称：

  作为PhotoCORM的 新型模块化锰（i）三羰基锰配合物：使用COP-1作为荧光开关探针在体外检测光诱导的一氧化碳释放†

  摘要：

  基于三齿双（吡唑基）乙胺（bpea）的五种通式为[Mn（bpea N CHC6H4R）（CO）3 ] PF 6和[Mn（bpea NHCH2C6H4R）（CO）3 ] PF 6的锰（I）三羰基配合物）合成并充分表征了每个配体，每个配体均包含一个带有4个取代基的侧基，R = H，I和C C–H，包括X射线结构分析的三种化合物。所有复合物在黑暗中在水性缓冲液中稳定较长时间。但是，CO释放可以通过在365 nm处照射来触发，从而将这些化合物确立为新型的可光活化的CO释放分子（PhotoCORM）。亚胺的影响与。借助DFT和TDDFT计算研究了电子结构和光物理行为的配体中的胺基。通过对所选化合物进行溶液IR研究，可以鉴定出由光反应产生的中间体。最后，使用COP-1作为荧光开关探针，在PBS缓冲液中和体外在人脐静脉内皮细胞（HUVEC）中都证明了光诱导的CO从模型化合物释放。

  DOI：

  10.1039/c4dt00254g

文献信息

• Metal complexes of new scorpionate ligands: 2,2′-Bis(pyrazolyl)ethylamine and its derivatives
  作者：Daniel L. Reger、Bryn Reinecke、Mark D. Smith、Radu F. Semeniuc

  DOI：10.1016/j.ica.2009.06.004

  日期：2009.9

  The new bis(pyrazolyl) amine ligand NH2CH2CH(pz)(2) (1) was prepared from the reaction of N-[2,2bis(pyrazolyl) ethyl]-1,8-naphthalimide with hydrazine monohydrate. A substituted derivative, C6H5CH2NHCH2CH(pz)(2) (2), was prepared by the reaction of 1 with benzaldehyde followed by reduction with NaBH4. Ligand 1 was also converted by two methods to the new bitopic, para-linked bis( pyrazolyl) amine ligand p-C6H4(CH2NHCH2CH(pz)(2))(2), (3). The reactions of the ligands 1-3 with [Cu(PPh3)(2)]NO3 yields (PPh3)Cu[(pz)(2)CHCH2NH2]}NO3, (PPh3)Cu[(pz)(2)CHCH2NHCH2C6H5]}NO3 and [(PPh3)Cu](2)[p((pz)(2)CHCH2NHCH2)(2)C6H4]}(NO3)(2)center dot solvate, respectively. Complex (N-3)(2)Cu[(pz)(2)CHCH2NHCH2C6H5]} was obtained from a methanol solution of 2, copper(II) acetate monohydrate and sodium azide. The complex Cd[(pz)(2)CHCH2NHCH2C6H5](2)}(PF6)(2)center dot 3C(3)H(6)O was synthesized by reaction of the protonated form of ligand 2, [(pz)(2)CHCH2NH2CH2C6H5]PF6, with Cd( acac) 2. In all of the structures the ligands are tridentate, bonding to the metal through the lone pair on the amine group as well as through the pyrazolyl rings they act as true scorpionates. The solid state structures all have extensive non-covalent interactions, with the N-H functional groups of the aminesparticipating in both N-H center dot center dot center dot p and N-H center dot center dot center dot O or N-H center dot center dot center dot N hydrogen bonding interactions. (C) 2009 Elsevier B.V. All rights reserved.
• New modular manganese(i) tricarbonyl complexes as PhotoCORMs: in vitro detection of photoinduced carbon monoxide release using COP-1 as a fluorogenic switch-on probe
  作者：Sandesh Pai、Maryam Hafftlang、George Atongo、Christoph Nagel、Johanna Niesel、Svetlana Botov、Hans-Günther Schmalz、Benito Yard、Ulrich Schatzschneider

  DOI：10.1039/c4dt00254g

  日期：——

  as novel photoactivatable CO-releasing molecules (PhotoCORMs). The influence of the imine vs. amine group in the ligands on the electronic structure and the photophysical behavior was investigated with the aid of DFT and TDDFT calculations. Solution IR studies on selected compounds allowed identification of intermediates resulting from the photoreaction. Finally, light-induced CO release from a model

  基于三齿双（吡唑基）乙胺（bpea）的五种通式为[Mn（bpea N CHC6H4R）（CO）3 ] PF 6和[Mn（bpea NHCH2C6H4R）（CO）3 ] PF 6的锰（I）三羰基配合物）合成并充分表征了每个配体，每个配体均包含一个带有4个取代基的侧基，R = H，I和C C–H，包括X射线结构分析的三种化合物。所有复合物在黑暗中在水性缓冲液中稳定较长时间。但是，CO释放可以通过在365 nm处照射来触发，从而将这些化合物确立为新型的可光活化的CO释放分子（PhotoCORM）。亚胺的影响与。借助DFT和TDDFT计算研究了电子结构和光物理行为的配体中的胺基。通过对所选化合物进行溶液IR研究，可以鉴定出由光反应产生的中间体。最后，使用COP-1作为荧光开关探针，在PBS缓冲液中和体外在人脐静脉内皮细胞（HUVEC）中都证明了光诱导的CO从模型化合物释放。
• New <i>N</i>,<i>N</i>,<i>N</i>-Heteroscorpionates Based on 2,2‘-Bis(pyrazolyl)ethanamine and Its Derivatives. Ligands Designed for Probing Supramolecular Interactions
  作者：Daniel L. Reger、Radu F. Semeniuc、James R. Gardinier、Jennifer O'Neal、Bryn Reinecke、Mark D. Smith

  DOI：10.1021/ic060347o

  日期：2006.5.1

  The successful design and synthesis of the new bis( pyrazolyl)ethanamine ligand and its copper( I) triphenylphosphine complex is reported. The ligand coordinates to the copper( I) center in a fac tridentate fashion, through both the pyrazolyl rings and the nitrogen atom from the NH2 group. In the solid state, the compound is organized in a 2D noncovalent network by N - H center dot center dot center dot pi and C - H center dot center dot center dot pi interactions and hydrogen bonds. The analogous ligand with a benzyl group substituted on the amine forms a complex with the same copper( I) center that has a similar 2D supramolecular structure and, in addition, is organized by the benzyl synthon into a 3D architecture.