N-benzyl-N',N'-dimethyl-N-(2-picolyl)ethylenediamine | 500771-64-2

• 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-benzyl-N',N'-dimethyl-N-(2-picolyl)ethylenediamine
• 英文别名: N'-benzyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine；N'-benzyl-N,N-dimethyl-N'-(pyridin-2-ylmethyl)ethane-1,2-diamine
• CAS: 500771-64-2
• 化学式: C₁₇H₂₃N₃
• 分子量: 269.39
• InChiKey: LSFUOGHUOQFWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-N',N'-dimethyl-N-(2-picolyl)ethylenediamine 以 四氢呋喃 、 氘代甲醇 为溶剂， 生成 [PtCF3SO3(N-benzyl-N',N'-dimethyl-N-(2-picolyl)ethylenediamine)]CF3SO3
  参考文献：
  名称：

  具有柔性三齿氮供体配体的甲基（氢化）铂（IV）配合物

  摘要：

  柔性的不对称三胺配体NNN = N，N，N'-三甲基-N '-（2-吡啶甲基）乙二胺（PICO），N-苄基-N '，N'-二甲基-N-（2-吡啶甲基）乙二胺（BPICO）和N，N '，N ''-五甲基二亚乙基三胺（PMDETA）在形成方形平面的二甲基二甲基铂（II）顺式-[PtMe 2（NNN）]配体中充当双齿配体。这些配合物与MeI进行氧化加成，得到fac- [PtMe 3（NNN）] I，其中配体是NNN FAC -tridentate在[PTME 3（NNN）]我当NNN = PICO或BPICO，但与二齿NNN在[PTIME平衡3（NNN）]当NNN = PMDETA。配合物的质子化的顺式- [PTME 2（NNN）]，得到相应的二甲基（氢基）铂（IV）配合物，[PtHMe 2（NNN）] X（X = BF 4 -，CF 3 SO 3 -，CF 3 CO 2 -），通常是异构体的混

  DOI：

  10.1021/om0206352
• 作为产物：
  描述：

  吡啶-2-甲醛 、 N'-苯甲基-N,N-二甲基乙二胺 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 42.0h， 以80%的产率得到N-benzyl-N',N'-dimethyl-N-(2-picolyl)ethylenediamine
  参考文献：
  名称：

  Olefin aziridination by copper(II) complexes: Effect of redox potential on catalytic activity

  摘要：

  A series of new copper(II) complexes of four sterically hindering linear tridentate 3N ligands N'-ethyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L1), N'-benzyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L2), N'-benzyl-N'-(6-methylpyrid-2-yl-methyl)-N,N-dimethylethylenediamine (L3) and N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine (L4) have been isolated and examined as catalysts for olefin aziridination. The complexes [Cu(L1)Cl-2]center dot CH3OH 1, [Cu(L2)Cl-2]center dot CH3OH 2, [Cu(L3)Cl-2]center dot 0.5 H2O 3 and [Cu(L4)Cl-2] 4 have been structurally characterized by X-ray crystallography. In all of them copper(II) adopts a slightly distorted square pyramidal geometry as inferred from the values of trigonality index (tau) for them (tau: 1, 0.02; 2, 0.01; 3, 0.07; 4, 0.01). Electronic and EPR spectral studies reveal that the complexes retain square-based geometry in solution also. The complexes undergo quasireversible Cu(II)/Cu(I) redox behavior (E-1/2, -0.272 - -0.454 V) in acetonitrile solution. The ability of the complexes to mediate nitrene transfer from PhINTs and chloramine-T trihydrate to olefins to form N-tosylaziridines has been studied. The complexes 3 and 4 catalyze the aziridination of styrene very slowly yielding above 80% of the desired product. They also catalyze the aziridination of the less reactive olefins like cyclooctene and n-hexene but with lower yields (30-50%). In contrast to these two complexes, 1 and 2 fail to catalyze the aziridination of olefins in the presence of both the nitrene sources. All these observations have been rationalized based on the Cu(II)/Cu(I) redox potentials of the catalysts. (C) 2010 Published by Elsevier B.V.

  DOI：

  10.1016/j.ica.2010.08.051

文献信息

• Synthesis, structure, spectra and reactivity of iron(iii) complexes of facially coordinating and sterically hindering 3N ligands as models for catechol dioxygenases
  作者：Karuppasamy Sundaravel、Thirumanasekaran Dhanalakshmi、Eringathodi Suresh、Mallayan Palaniandavar

  DOI：10.1039/b809142k

  日期：——

  N-dimethylformamide and dichloromethane solutions. The adducts [Fe(L)(DBC)(Sol)]+ undergo cleavage of DBC2− in the presence of molecular oxygen to afford both intra- and extradiol cleavage products. The extradiol products are higher in dichloromethane than in DMF solution and the extradiol to intradiol product selectivity (E/I, 7.2 : 1–18.5 : 1) observed decreases upon increasing the steric bulk of N-alkyl substituent

  位阻和系统修饰的三齿3N供体的一系列1：1铁（III）配合物配体 已被分离出来并作为二醇外切的功能模型进行了研究 儿茶酚双加氧酶。它们均为[Fe（L）Cl 3 ]类型，其中L为N-甲基-N '-（吡啶-2-基甲基）乙二胺 （L1）， N-乙基-N '-（吡啶-2-基甲基）乙二胺 （L2）， N-苄基-N '-（吡啶-2-基甲基）乙二胺 （L3）， N，N-二甲基-N '-（吡啶-2-基甲基）乙二胺 （L4）， N′-甲基-N ′-（吡啶-2-基甲基）-N，N-二甲基乙二胺 （L5）， N′-乙基-N ′-（吡啶-2-基甲基）-N，N-二甲基乙二胺 （L6）和 N'-苄基-N '-（吡啶-2-基甲基）-N，N-二甲基乙二胺（L7）。他们的特点是元素分析以及光谱和电化学方法。已经成功地确定了配合物[Fe（L2）Cl 3 ] 2，[Fe（L3）Cl 3 ] 3和[Fe（L7）Cl 3 ] 7的X
• Olefin aziridination by copper(II) complexes: Effect of redox potential on catalytic activity
  作者：Thirumanasekaran Dhanalakshmi、Eringathodi Suresh、Mallayan Palaniandavar

  DOI：10.1016/j.ica.2010.08.051

  日期：2011.1

  A series of new copper(II) complexes of four sterically hindering linear tridentate 3N ligands N'-ethyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L1), N'-benzyl-N'-(pyrid-2-ylmethyl)-N,N-dimethylethylenediamine (L2), N'-benzyl-N'-(6-methylpyrid-2-yl-methyl)-N,N-dimethylethylenediamine (L3) and N'-benzyl-N'-(quinol-2-ylmethyl)-N,N-dimethylethylenediamine (L4) have been isolated and examined as catalysts for olefin aziridination. The complexes [Cu(L1)Cl-2]center dot CH3OH 1, [Cu(L2)Cl-2]center dot CH3OH 2, [Cu(L3)Cl-2]center dot 0.5 H2O 3 and [Cu(L4)Cl-2] 4 have been structurally characterized by X-ray crystallography. In all of them copper(II) adopts a slightly distorted square pyramidal geometry as inferred from the values of trigonality index (tau) for them (tau: 1, 0.02; 2, 0.01; 3, 0.07; 4, 0.01). Electronic and EPR spectral studies reveal that the complexes retain square-based geometry in solution also. The complexes undergo quasireversible Cu(II)/Cu(I) redox behavior (E-1/2, -0.272 - -0.454 V) in acetonitrile solution. The ability of the complexes to mediate nitrene transfer from PhINTs and chloramine-T trihydrate to olefins to form N-tosylaziridines has been studied. The complexes 3 and 4 catalyze the aziridination of styrene very slowly yielding above 80% of the desired product. They also catalyze the aziridination of the less reactive olefins like cyclooctene and n-hexene but with lower yields (30-50%). In contrast to these two complexes, 1 and 2 fail to catalyze the aziridination of olefins in the presence of both the nitrene sources. All these observations have been rationalized based on the Cu(II)/Cu(I) redox potentials of the catalysts. (C) 2010 Published by Elsevier B.V.
• Methyl(hydrido)platinum(IV) Complexes with Flexible Tridentate Nitrogen-Donor Ligands
  作者：Ernest M. Prokopchuk、Richard J. Puddephatt

  DOI：10.1021/om0206352

  日期：2003.2.1

  unsymmetrical triamine ligands NNN = N,N,N‘-trimethyl-N‘-(2-pyridylmethyl)ethylenediamine (PICO), N-benzyl-N‘,N‘-dimethyl-N-(2-picolyl)ethylenediamine (BPICO), and N,N‘,N‘ ‘-pentamethyldiethylenetriamine (PMDETA) act as bidentate ligands in forming square-planar dimethylplatinum(II) complexes cis-[PtMe2(NNN)]. These complexes undergo oxidative addition with MeI to give the platinum(IV) complexes fac-[PtMe3(NNN)]I

  柔性的不对称三胺配体NNN = N，N，N'-三甲基-N '-（2-吡啶甲基）乙二胺（PICO），N-苄基-N '，N'-二甲基-N-（2-吡啶甲基）乙二胺（BPICO）和N，N '，N ''-五甲基二亚乙基三胺（PMDETA）在形成方形平面的二甲基二甲基铂（II）顺式-[PtMe 2（NNN）]配体中充当双齿配体。这些配合物与MeI进行氧化加成，得到fac- [PtMe 3（NNN）] I，其中配体是NNN FAC -tridentate在[PTME 3（NNN）]我当NNN = PICO或BPICO，但与二齿NNN在[PTIME平衡3（NNN）]当NNN = PMDETA。配合物的质子化的顺式- [PTME 2（NNN）]，得到相应的二甲基（氢基）铂（IV）配合物，[PtHMe 2（NNN）] X（X = BF 4 -，CF 3 SO 3 -，CF 3 CO 2 -），通常是异构体的混