N-phenyl-N′-(p-tolyl)ethane-1,2-diamine

• 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-phenyl-N′-(p-tolyl)ethane-1,2-diamine
• 英文别名: N1-phenyl-N2-p-tolylethane-1,2-diamine；N-phenyl-N'-p-tolyl-ethylenediamine；N-Phenyl-N'-p-tolyl-aethylendiamin；N'-(4-methylphenyl)-N-phenylethane-1,2-diamine
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: VUDMHQLTKFJKFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-N′-(p-tolyl)ethane-1,2-diamine 在 2,6-二甲基吡啶 、 dipotassium hydrogenphosphate 、 三氟甲磺酸三甲基硅酯 、 potassium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 (4,5-dimethoxy-2-nitrophenyl)(4-((pyridin-2-ylmethyl)(2-((pyridin-2-ylmethyl)(p-tolyl)amino)ethyl)amino)phenyl)methanol
  参考文献：
  名称：

  Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺Photocages Using Multiple Nitrobenzyl Groups

  摘要：

  Two generations of DiCast photocages that exhibit light-induced decreases in metal ion affinity have been prepared and characterized. Expansion of the common Zn2+ chelator of N,N-dipicolylaniline (DPA) to include additional aniline ligand provides N,N'-diphenyl-N,N'-bis(pyridin-2-ylmethyl)ethane-1,2-diamine, a tetradentate ligand that was functionalized with two photolabile groups to afford DiCast-1. Uncaging of the nitrobenzhydrol reduces the electron density on two metal bound aniline ligands, which decreases the Zn2+ affinity 190 fold The analogous MonoCast photocage with a single nitrobenzhydrol group only undergoes a 14 fold reduction in affinity after an identical photochemical transformation. A second series of DiCast photocages based on a N,Ni-(pyridine-2,6-diylbis(methylene))dianiline scaffold, which allows the introduction of two additional Zn2+-binding ligands into a preorganized chelator, expand on the multi-photolabile group strategy. DiCast-2 includes two pyridine ligands while DiCast-3 adds two carboxylate groups. Addition of bridging pyridine to the second generation photocages leads to more stable Zn2+ complexes, and photolysis of two photolabile groups increases the Zn2+ affinity changes to 480 fold The Zn2+, Cu2+, and Cd2+ binding properties were examined in all the DiCast photocages and the corresponding photoproducts using UV-vis spectroscopy. Further insight into the photocage Zn2+-binding motifs was obtained by X-ray analysis of DiCast-2 and DiCast-3 model ligands.

  DOI：

  10.1021/ic400465g
• 作为产物：
  描述：

  对氯甲苯 、 N-苯基乙二胺 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 N-[2-二(1-金刚烷)磷苯基]吗啉 、 sodium t-butanolate 作用下， 反应 21.0h， 以85%的产率得到N-phenyl-N′-(p-tolyl)ethane-1,2-diamine
  参考文献：
  名称：

  Buchwald-Hartwig 在无水和无溶剂条件下使用 Mor-DalPhos 对（杂）芳基氯化物进行胺化

  摘要：

  我们报告了 [Pd(cinnamyl)Cl]2/Mor-DalPhos 催化剂体系在（杂）芳基氯化物与伯胺或仲胺的 Buchwald-Hartwig 胺化中的应用，该胺化反应在水性条件下进行，不使用共溶剂和/或表面活性剂或在无溶剂条件下（52 个例子）。We have established that reactions of this type can be conducted without the rigorous exclusion of air, and in the case of the solvent-free reactions, we have demonstrated that appropriately selected liquid and solid reagents can be employed successfully.

  DOI：

  10.1002/ejoc.201200510

文献信息

• Reversible Hydride Transfer to <i>N</i>,<i>N</i>′-Diarylimidazolinium Cations from Hydrogen Catalyzed by Transition Metal Complexes Mimicking the Reaction of [Fe]-Hydrogenase
  作者：Masahiro Hatazawa、Naoko Yoshie、Hidetake Seino

  DOI：10.1021/acs.inorgchem.7b00806

  日期：2017.7.17

  the single metal active site, several transition metal complex catalysts capable of such activation were utilized in the model system. Reduction of 1[BF4] to N,N′-diphenylimidazolidine (2) was achieved under 1 atm H2 at ambient temperature in the presence of an equimolar amount of NEt3 as a proton acceptor. The proposed catalytic pathways involved the generation of active hydride complexes and subsequent

  [Fe]-加氢酶是参与甲烷生成的关键酶，可促进氢化物从H 2到N 5，N 10-亚甲基四氢甲基蝶呤（CH-H 4 MPT +）的可逆转移。在这项研究中，通过使用N，N'-二苯基咪唑啉鎓阳离子（1 +）作为CH-H 4 MPT +的结构相关替代物，开发了一个反应系统来模拟[Fe]-氢化酶的酶功能。通过H 2的异源裂解与酶促机制有关在单个金属活性位点，模型系统中使用了几种能够活化的过渡金属络合物催化剂。在等摩尔量的NEt 3作为质子受体的存在下，在环境温度1 atm H 2下，在环境温度为1 atm H 2的条件下，将1 [BF 4 ]还原为N，N'-二苯基咪唑烷（2）。拟议的催化途径涉及活性氢化物配合物的产生和随后的分子间氢化物转移至1 +。通过用HNMe 2 Ph +处理2可以完成逆反应。作为质子源，其中，[（η 5 -C 5我5）IR （p -MeC 6 ħ 4 SO 2）NCHPhCHPhNH}]被发现催化形成1
• Buchwald-Hartwig Amination of (Hetero)aryl Chlorides by Employing Mor-DalPhos under Aqueous and Solvent-Free Conditions
  作者：Bennett J. Tardiff、Mark Stradiotto

  DOI：10.1002/ejoc.201200510

  日期：2012.7

  catalyst system in the Buchwald–Hartwig amination of (hetero)aryl chlorides with primary or secondary amines conducted either under aqueous conditions without the use of co-solvents and/or surfactants or under solvent-free conditions (52 examples). We have established that reactions of this type can be conducted without the rigorous exclusion of air, and in the case of the solvent-free reactions, we have

  我们报告了 [Pd(cinnamyl)Cl]2/Mor-DalPhos 催化剂体系在（杂）芳基氯化物与伯胺或仲胺的 Buchwald-Hartwig 胺化中的应用，该胺化反应在水性条件下进行，不使用共溶剂和/或表面活性剂或在无溶剂条件下（52 个例子）。We have established that reactions of this type can be conducted without the rigorous exclusion of air, and in the case of the solvent-free reactions, we have demonstrated that appropriately selected liquid and solid reagents can be employed successfully.
• Jur'ew; Gorin, Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1444,1446; engl. Ausg. S. 1429, 1430
  作者：Jur'ew、Gorin

  DOI：——

  日期：——
• US4161528A
  申请人：——

  公开号：US4161528A

  公开（公告）日：1979-07-17
• Rational and Predictable Chemoselective Synthesis of Oligoamines via Buchwald–Hartwig Amination of (Hetero)Aryl Chlorides Employing Mor-DalPhos
  作者：Bennett J. Tardiff、Robert McDonald、Michael J. Ferguson、Mark Stradiotto

  DOI：10.1021/jo202358p

  日期：2012.1.20

  We report a diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald–Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl]2/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl)morpholine, Mor-DalPhos). Competition reactions established the following relative preference of this catalyst system for amine

  我们报告了通过使用布赫瓦尔德-哈特维格胺胺化（采用单一催化剂体系）[[Pd（cinnamyl）Cl] 2 / L1 ; L1）在二胺，三胺和四胺的合成中合成有用的化学选择性的多种证明（62个实例）＝N-（2-（二（1-（金刚烷基）膦基）苯基）吗啉，Mor-DalPhos）。竞争反应确定了该催化剂体系对胺偶联伙伴的以下相对偏爱：线性伯烷基胺和亚胺>无阻碍的富电子伯苯胺，伯，N，N-二烷基肼和环状伯烷基胺>无阻碍的电子缺陷伯胺，α-支链无环伯烷基胺，受阻电子伯胺苯胺和伯酰胺。制备了新的异构体配体N-（4-（二（1-（金刚烷基）膦基）苯基）吗啉（p -Mor-DalPhos，L2），产率为63％，并进行了晶体学表征。[Pd（肉桂基）Cl] 2 / L2催化剂体系表现出不同的反应性。建立[Pd（肉桂基）Cl] 2 / L1的反应性趋势的应用实现了对二胺，三胺和四胺的化学选择性合成。在2-（4-氨基