2,2'-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(4-methylphenol) | 761412-87-7

• 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: 2,2'-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(4-methylphenol)
• 英文别名: 2-[[2-(Dimethylamino)ethyl-[(2-hydroxy-5-methylphenyl)methyl]amino]methyl]-4-methylphenol；2-[[2-(dimethylamino)ethyl-[(2-hydroxy-5-methylphenyl)methyl]amino]methyl]-4-methylphenol
• CAS: 761412-87-7
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: NUTGIFNWUISMMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四氢呋喃 、 2,2'-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(4-methylphenol) 在 methyllithium lithium bromide 、 甲基锂 作用下， 以 乙醚 为溶剂， 反应 1.25h， 以71.1%的产率得到
  参考文献：
  名称：

  Lithium diaminebis(aryloxido) complexes: Synthesis, structures and reactivity in l-lactide polymerization

  摘要：

  Lithium compounds of the tetradentate diaminebis(aryloxido) ligand [Li-6(mu-L-kappa O-4,N,N,O)(2)(mu(3)-X)(2)(thf)(4)] (1, X = Br; 2, X = I) (I.= [Me2NCH2CH2N(CH2-4-Me-C6H3O)(2)](2-)} were synthesized in high yield using conventional deprotonation procedure as recently described for [Li-6(mu-L-kappa O-4,N,N,O)(2)(mu(3)-Cl)(2)(thf)(4)] (3). The ligand precursor H2L was reacted with Me Li and LiX (X = Br, I) in thf to give related hexametallic species 1 and 2. Substitution of thf molecules in 1 by benzyl alcohol generates [Li-6(mu-L-kappa O-4,N,N,O)(2)(mu-Br)(2) (BnOH)(4)] (4). A moisture causes partial hydrolization of 4 to form ionic species [Li-4(mu-L-kappa O-4,N,N,O) (mu-LH-kappa O-4,N,O)(mu-H2O)(2)(BnOH)(2)]Br (5). Compounds 1, 2, 4 and 5 were characterized by chemical and physical techniques including X-ray crystallography for 1.thf, 4 and 5. The molecular structures of 1 and 4 contain the same Li6O4X2 core but they differ in the coordination mode of bromides, mu(3)-Br in 1 and mu-Br in 4. The cation of 5 adopts a ladder-like conformation, closed by the intramolecular hydrogen interactions. Preliminary experimental results show that 1-3 in the presence of benzyl alcohol efficiently initiate the ring-opening polymerization of L-lactide yielding isotactic polymers with relatively narrow polydispersity indexes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.10.006
• 作为产物：
  描述：

  对甲酚 、 N,N-二甲基乙二胺 在 paraformaldehyde 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2,2'-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(4-methylphenol)
  参考文献：
  名称：

  Magnesium, zinc and aluminium complexes supported by tripodal diaminebis(aryloxido) ligands: synthesis, solid state and solution structure

  摘要：

  二氨基双(芳基氧)配体前体[Me2NCH2CH2N(CH2-4-R-C6H3OH)2][R = C(CH3)2CH2C(CH3)3, H22L11；R＝CH3，H22L22]与 MgnBu2、ZnEt2 和 AlEt3 生成通式为[M2(μ-L-κ4O,N,N,O)2]（M＝Mg，1a 表示 L1，1b 表示 L2；M＝Zn，2a 表示 L1，2b 表示 L2）和[Al2(μ-L-κ3O,N,N,O)2Et2]（3 表示 L1）的复合物。通过核磁共振光谱和 ESI-MS 实验对化合物 1a-3 进行了表征。单晶分析提供了 1b-CH2Cl2、2a-H2O、2b-CH2Cl2 和 3 的确切分子结构，并揭示了它们具有 M2O2 平面核心的二聚体性质。核磁共振光谱显示，这些化合物的固态基本上保留在溶液中。

  DOI：

  10.1039/c3dt50938a

文献信息

• Accelerated syntheses of amine-bis(phenol) ligands in polyethylene glycol or “on water” under microwave irradiation
  作者：Francesca M Kerton、Stacey Holloway、Angela Power、R Graeme Soper、Kristina Sheridan、Jason M Lynam、Adrian C Whitwood、Charlotte E Willans

  DOI：10.1139/v08-043

  日期：2008.5.1

  Pure amine-bis(phenol) ligands are readily accessible in high yield, often >90%, when the Mannich condensation reactions are performed “on water” or in poly(ethyleneglycol) (PEG). Microwave-assisted synthesis dramatically reduces the time and energy required to prepare these molecules, typically from 24 h to 5 min. The approach seems to be widely applicable (7 amines and 5 phenols were tested to yield a diverse set of bis(phenol) ligands). Significant improvements in yield were observed for ligands derived from di-tert-amyl and di-tert-butyl phenols, possibly resulting from a hydrophobic effect. Single crystal X-ray diffraction data for the ligand derived from p-cresol and N,N′-dimethylethylenediamine is reported.Key words: amine-phenol, Mannich condensation, on water, microwave, ligand, high-throughput.

  当曼尼希缩合反应在 "水上 "或聚（乙二醇）（PEG）中进行时，很容易获得纯胺-双（酚）配体，而且收率很高，通常可达 90%。微波辅助合成大大减少了制备这些分子所需的时间和能量，通常可从 24 小时缩短到 5 分钟。这种方法似乎具有广泛的适用性（对 7 种胺和 5 种酚进行了测试，得到了多种双（酚）配体）。从二叔戊基苯酚和二叔丁基苯酚衍生出的配体的产率显著提高，这可能是疏水效应的结果。报告了由对甲酚和 N,N′-二甲基乙二胺衍生的配体的单晶 X 射线衍射数据。 关键词：胺-酚、曼尼希缩合、水、微波、配体、高通量。
• Synthesis, characterization and phosphotriesterase mimetic activity of some Zn(II) and Cu(II) complexes
  作者：MAMATA SINGH、RAY J BUTCHER、JERRY P JASINSKI、JAMES A GOLEN、GOVINDASAMY MUGESH

  DOI：10.1007/s12039-012-0331-4

  日期：2012.11

  the synthesis and characterization of a few phenolate-based ligands bearing tert- amino substituent and their Zn(II) and Cu(II) metal complexes. Three mono/binuclear Zn(II) and Cu(II) complexes [Zn(L1)(H2O)].CH3OH.H2O (1) (H 2 L1 = 6,6′-(((2-dimethylamino)ethylazanediyl)bis(methylene))bis(2, 4-dimethylphenol), [Zn2(L2)2] (2) (H 2 L2 = 2,2′-(((2-dimethylamino)ethyl)azanediyl)bis(methylene)bis(4- methylphenol)

  我们在这里报告了一些带有叔氨基取代基的酚盐基配体及其Zn（II）和Cu（II）金属配合物的合成和表征。三种单/双核Zn（II）和Cu（II）配合物[Zn（L1）（H 2 O）]。CH 3 OH.H 2 O （1）（H 2 L1 = 6,6 ′ -（（（2 -（二甲基氨基）乙基氮杂二基）双（亚甲基））双（2，4-二甲基苯酚），[Zn 2（L2）2 ] （2）（H 2 L2 = 2,2 ' -（（（（2-二甲基氨基）乙基）氮杂二基）二（亚甲基）二 （4-甲基苯酚）和[Cu 2（L3）2 .CH 2 Cl 2 ] （3）（H 2 L3 =（6,6 ' -（（（（2-（二乙基氨基）乙基）氮杂二基）双（亚甲基））双（亚甲基）双（2,4-二甲基苯酚）是通过使用三个对称的含有N 2 O 2供体位点的对称四齿碳酸盐配体合成的，这些络合物通过多种技术进行表征，包括元素分析，质谱，1 H，13 C NMR光谱和单晶X射线分析。借助31
• A high-throughput approach to lanthanide complexes and their rapid screening in the ring opening polymerisation of caprolactone
  作者：Francesca M. Kerton、Adrian C. Whitwood、Charlotte E. Willans

  DOI：10.1039/b406841f

  日期：——

  lanthanum and praseodymium, and the smaller lanthanides like ytterbium. X-ray crystal structures of a sterically demanding chelating amine-bis((2-hydroxyaryl)methyl) ligand and a chloride bridged dinuclear gadolinium complex are reported. The centrosymmetric molecule contains gadolinium in distorted capped trigonal prismatic environments bonded to two amine, two phenolate, one THF and two chloride

  使用高通量方法已经合成了由含氮和氧的配体支撑的镧系元素络合物的库。该配合物用于ε-己内酯的开环聚合中，在某些情况下提供分子量可控且多分散性窄的聚己内酯。开发了基于21个配体和8种镧系元素试剂的文库，以确定镧系金属和配体的最佳组合。它们是通过[Ln [N（SiMe（3））（2）]（3）]配合物与含有氧和氮供体的四齿双阴离子配体的氨基转移反应制备的。1 H NMR光谱用于筛选聚合活性。配位体的空间需求对聚合过程有重要影响，氮供体的类型和中心Ln（3+）离子的大小也一样。含有具有大取代基如叔戊基的芳基环的配体提供了能够进行己内酯受控聚合的物质，而较小的基团如甲基则无效。与较大的镧系元素，镧和以及较小的镧系元素（如）相比，钇和中等尺寸的镧系元素（如sa）显示出更高的活性。报道了空间上需要的螯合胺-双（（2-羟基芳基）甲基）配体和氯桥联的双核g配合物的X射线晶体结构。中心对称分子在扭曲的带帽三角棱柱
• Lithium complexes supported by tripodal diaminebis(aryloxido) ligands: Synthesis and structure
  作者：Zofia Janas、Tomasz Nerkowski、Ewa Kober、Lucjan B. Jerzykiewicz、Tadeusz Lis

  DOI：10.1039/c1dt11498k

  日期：——

  The diaminebis(aryloxido) ligand precursors H2L1 and H2L2 [H2L1 = Me2NCH2CH2N(CH2-4-CMe2CH2CMe3-C6H3OH)2; H2L2 = Me2NCH2CH2N(CH2-4-Me-C6H3OH)2] were synthesized by a straightforward single-step Mannich condensation. Their reactions with 2 molar equivalents of MeLi in thf afforded [Li4(μ-L-κ4O,N,N,O)2(thf)2] (1a, L1; 1b, L2) and unexpectedly small amounts (∼9%) of [Li6(μ-L-κ4O,N,N,O)2(μ3-Cl)2(thf)4]·thf

  二胺双（芳基氧基）配体前体H 2 L 1和H 2 L 2 [H 2 L 1＝ Me 2 NCH 2 CH 2 N（CH 2 -4-CMe 2 CH 2 CMe 3 -C 6 H 3 OH）2。H 2 L 2 = Me 2 NCH 2 CH 2 N（CH 2 -4-Me-C 6 H 3 OH）2通过简单的单步曼尼希缩合反应合成[]。他们的反应与2摩尔当量的梅里在THF中，得到[李4（μ-L-κ 4 ø，Ñ，Ñ，ö）2（THF）2 ]（1a中，L 1 ;图1b，L 2）和出乎意料地少量（〜9％）的[李6（μ-L-κ 4 ø，ñ，ñ，ö）2（μ 3 -Cl）2（THF）4 ]·THF（2A ·THF，L 1 ; 2B ·THF，L 2）。LiCl的化学计量反应，梅里配体前体H 2 L导致高产率（〜80％）形成2a和2b。通过化学和物理技术，包括X射线晶体用于h所有化合物，其特征在于2大号1，H 2大号2，1B，2A和2B。
• Lithium diaminebis(aryloxido) complexes: Synthesis, structures and reactivity in l-lactide polymerization
  作者：Ewa Kober、Rafał Petrus、Paulina Kocięcka、Zofia Janas、Piotr Sobota

  DOI：10.1016/j.poly.2014.10.006

  日期：2015.1

  Lithium compounds of the tetradentate diaminebis(aryloxido) ligand [Li-6(mu-L-kappa O-4,N,N,O)(2)(mu(3)-X)(2)(thf)(4)] (1, X = Br; 2, X = I) (I.= [Me2NCH2CH2N(CH2-4-Me-C6H3O)(2)](2-)} were synthesized in high yield using conventional deprotonation procedure as recently described for [Li-6(mu-L-kappa O-4,N,N,O)(2)(mu(3)-Cl)(2)(thf)(4)] (3). The ligand precursor H2L was reacted with Me Li and LiX (X = Br, I) in thf to give related hexametallic species 1 and 2. Substitution of thf molecules in 1 by benzyl alcohol generates [Li-6(mu-L-kappa O-4,N,N,O)(2)(mu-Br)(2) (BnOH)(4)] (4). A moisture causes partial hydrolization of 4 to form ionic species [Li-4(mu-L-kappa O-4,N,N,O) (mu-LH-kappa O-4,N,O)(mu-H2O)(2)(BnOH)(2)]Br (5). Compounds 1, 2, 4 and 5 were characterized by chemical and physical techniques including X-ray crystallography for 1.thf, 4 and 5. The molecular structures of 1 and 4 contain the same Li6O4X2 core but they differ in the coordination mode of bromides, mu(3)-Br in 1 and mu-Br in 4. The cation of 5 adopts a ladder-like conformation, closed by the intramolecular hydrogen interactions. Preliminary experimental results show that 1-3 in the presence of benzyl alcohol efficiently initiate the ring-opening polymerization of L-lactide yielding isotactic polymers with relatively narrow polydispersity indexes. (C) 2014 Elsevier Ltd. All rights reserved.