N,N'-bis(3,5-dimethylphenyl)-1,2-ethanediamine

• 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,N'-bis(3,5-dimethylphenyl)-1,2-ethanediamine
• 英文别名: Bis(3,5-dimethylphenyl) ethylenediamine；N,N'-bis(3,5-dimethylphenyl)ethane-1,2-diamine
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: ABKGBXZLUUPIBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate 、 N,N'-bis(3,5-dimethylphenyl)-1,2-ethanediamine 在 高氯酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 6-formyl-2,3-dihydro-1,4-bis(3,5-dimethylphenyl)-1,4-diazepinium perchlorate
  参考文献：
  名称：

  The p-Donor Ability of Vinamidine Chelates (Co, Ni, Cu, Zn, Pd) Assessed by X-Ray, IR and NMR

  摘要：

  Formyl groups were used as reporter substituents attached to positions with high pi-electron densities in the vinamidine moieties of a 2,3-dihydro-1,4-diazepinium cation (7a) and of five metal complexes (9a-e). X-Ray structure analyses of the latter indicated significant pi donation to the coplanar formyl groups but insignificant changes of the formyl geometry. Infrared wave numbers in solution revealed a weak pi donation from the vinamidinium system (79) and a uniformly strong one from the metal bis(chelates) (9a-e), but infrared intensities were inconclusive. However, clear evidence emerged from the rates of aldehyde rotation at the vinamidine moieties, as measured for these diamagnetic or paramagnetic heterocycles by H-1 nmr: The pi-donor chararacters were energetically quantified by comparisons of literature data with the rotational barriers 11.0 kcal/mol at vinamidinium(in 79) and 14.7-15.8 kcal/mol at vinamidin(id)e (in 9a, b, d and e).

  DOI：

  10.3987/com-94-s38
• 作为产物：
  描述：

  聚合甲醛 、 5-硝基间二甲苯 在 甲酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 水 为溶剂， 以67 %的产率得到N,N'-bis(3,5-dimethylphenyl)-1,2-ethanediamine
  参考文献：
  名称：

  硝基芳烃和 HCHO 的还原偶联用于钴单原子催化剂通用合成功能性 1,2-二胺

  摘要：

  尽管应用广泛，但迄今为止，选择性和多样化地获取N,N'-二芳基乙烷-1,2-二胺仍然是一个挑战。在这里，通过开发一种双功能钴单原子催化剂（Co SA -N/NC），我们提出了一种通过廉价且丰富的硝基芳烃和甲醛的选择性还原偶联直接合成此类化合物的通用方法，具有良好的底物和功能相容性，一种易于获得的贱金属催化剂，具有出色的可重复使用性以及高步骤效率和原子效率。机理研究表明，N锚定的钴单原子（CoN 4）作为还原过程的催化活性位点，N掺杂的碳载体富集了HCHO，及时捕获了原位形成的羟胺，并在弱电条件下提供了所需的硝酮。碱性条件下，随后硝酮和亚胺的逆电子需求1,3-偶极环加成反应，随后环加合物的加氢脱氧反应提供产物。在这项工作中，催化剂控制的硝基芳烃还原原位产生特定结构单元的概念预计将开发出更有用的化学转化。

  DOI：

  10.1021/jacs.3c04857

文献信息

• β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction
  作者：Pedro J. Llabres-Campaner、Rafael Ballesteros-Garrido、Rafael Ballesteros、Belén Abarca

  DOI：10.1016/j.tet.2017.08.006

  日期：2017.9

  Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture

  与纯乙二醇的借入氢（BH）也称为氢自动转移（HA），是制备β-氨基醇的关键步骤。然而，由于乙二醇的稳定性，很少实现单活化。在此，据报道Pd / C和ZnO的组合作为该BH / HA反应的非均相催化剂。该系统产生了极好的空气和湿气稳定性，并且经济的催化剂能够将水中的乙二醇单官能化，而无需进一步活化二醇。在这项工作中，已经探索了不同的二醇和芳族胺，为氨基醇的开发提供了一种新方法。这项研究揭示了两种固体物质的组合如何在异相中提供有趣的催化性能。ZnO激活乙二醇，而Pd / C则负责BH / HA循环。重新芳香化之前的原位BH / HA循环，代表串联异质过程。
• Organometallic ruthenium complexes and related methods for the preparation of tetra-substituted and other hindered olefins
  申请人：Berlin Jacob

  公开号：US20070282148A1

  公开（公告）日：2007-12-06

  The invention relates to ruthenium alkylidene complexes having an N-heterocyclic carbene ligand comprising a 5-membered heterocyclic ring having a carbenic carbon atom and at least one nitrogen atom contained within the 5-membered heterocyclic ring, wherein the nitrogen atom is directly attached to the carbenic carbon atom and is substituted by a phenyl ring, and wherein the phenyl ring has a hydrogen at either or both ortho positions and is substituted at at least one ortho or meta position. The invention also relates to an olefin metathesis reactions and particularly to the preparation of tetra-substituted cyclic olefins via a ring-closing metathesis.

  本发明涉及具有N-杂环卡宾配体的钌烷基烯配合物，包括一个含有卡宾碳原子和至少一个氮原子的5元杂环环的杂环卡宾配体，其中氮原子直接连接到卡宾碳原子，并被苯环取代，苯环在两个邻位或一个邻位和一个间位处有氢原子，并在至少一个邻位或间位被取代。本发明还涉及烯烃交换反应，特别是通过环闭合交换反应制备四取代环烯烃。
• ORGANOMETALLIC RUTHENIUM COMPLEXES AND RELATED METHODS FOR THE PREPARATION OF TETRA-SUBSTITUTED AND OTHER HINDERED OLEFINS
  申请人：BERLIN Jacob

  公开号：US20120123133A1

  公开（公告）日：2012-05-17

  The invention relates to ruthenium alkylidene complexes having an N-heterocyclic carbene ligand comprising a 5-membered heterocyclic ring having a carbenic carbon atom and at least one nitrogen atom contained within the 5-membered heterocyclic ring, wherein the nitrogen atom is directly attached to the carbenic carbon atom and is substituted by a phenyl ring, and wherein the phenyl ring has a hydrogen at either or both ortho positions and is substituted at at least one ortho or meta position. The invention also relates to an olefin metathesis reactions and particularly to the preparation of tetra-substituted cyclic olefins via a ring-closing metathesis.

  本发明涉及一种具有N-杂环卡宾配体的钌烯烃配合物，其中该配体包含一个5元杂环环，该环具有一个卡宾烯碳原子和至少一个氮原子，所述氮原子直接连接在卡宾烯碳原子上，并被苯环取代，所述苯环在其两个邻位上具有氢原子，并在至少一个邻位或间位上被取代。本发明还涉及烯烃交换反应，特别是通过环闭合烯烃交换反应制备四取代环状烯烃。
• US4161528A
  申请人：——

  公开号：US4161528A

  公开（公告）日：1979-07-17
• US8008224B2
  申请人：——

  公开号：US8008224B2

  公开（公告）日：2011-08-30