3,4,5,6,7,8-Hexamethyl-1,10-phenanthrolin | 3002-87-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 3,4,5,6,7,8-Hexamethyl-1,10-phenanthrolin
• 英文别名: 3,4,5,6,7,8-Hexamethyl-1,10-phenanthroline
• CAS: 3002-87-7
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: HSWXQAVRNLVYDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(pentamethylcyclopentadienyl)ytterbium(diethyl ether) 、 3,4,5,6,7,8-Hexamethyl-1,10-phenanthrolin 以 乙醚 为溶剂， 反应 2.5h， 以70%的产率得到Cp*₂Yb(3,4,5,6,7,8-Me₆phen)
  参考文献：
  名称：

  Carbon–Hydrogen Bond Breaking and Making in the Open-Shell Singlet Molecule Cp*₂Yb(4,7-Me₂phen)

  摘要：

  The adducts formed between the 4,7-Me-2-, 3,4,7,8-Me-4-, and 3,4,5,6,7,8-Me-6-phenanthroline ligands and Cp*Yb-2 are shown to have open-shell singlet ground states by magnetic susceptibility and LIII-edge XANES spectroscopy. Variable-temperature XANES data show that two singlet states are occupied in each adduct that are fit to a Boltzmann distribution for which Delta H = 5.75 kJ mol(-1) for the 4,7-Me(2)phen adduct. The results of a CASSCF calculation for the 4,7-Me(2)phen adduct indicates that three open-shell singlet states, SS1SS3, lie 0.44, 0.06. and 0.02 eV, respectively, below the triplet state. These results are in dramatic contrast to those acquired for the phenanthroline and 5,6-Me(2)phen adducts, which are ground state triplets ( J. Am. Chem. Soc. 2014, 136, 8626). A model that accounts for these differences is traced to the relative energies of the LUMO and LUMO+1 orbitals that depend on the position the methyl group occupies in the phenanthroline ligand. The model also accounts for the difference in reactivities of Cp*Yb-2(3,8-Me(2)phen) and Cp*Yb-2(4,7-Me(2)phen); the former forms a s CC bond between C(4)C(4'), and the latter undergoes CH bond cleavage at the methyl group on C(4) and leads to two products that cocrystallize: Cp*Yb-2(4-(CH2),7-Mephen), which has lost a hydrogen atom, and Cp*Yb-2(4,7-Me-2-4H-phen), which has gained a hydrogen atom.

  DOI：

  10.1021/om500843z
• 作为试剂：
  描述：

  6,7-dihydro-1H-pyrrolo[3,2-c]pyridine-1,5(4H)-dicarboxylic acid di tert-butyl ester 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 3,4,5,6,7,8-Hexamethyl-1,10-phenanthrolin 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  CN115806561

  摘要：

  公开号：

文献信息

• Substituted 1,10-phenanthrolines
  申请人：EASTMAN KODAK COMPANY (a New Jersey corporation)

  公开号：EP0339973A1

  公开（公告）日：1989-11-02

  Lipophilic 1,10-phenanthrolines having one or more substituents are described. These compounds have the structure: wherein R is selected from the group consisting of alkyl having a molecular weight of at least 45, cycloalkyl having 5 to 10 carbon atoms in the ring and substituted phenyl, R′ is either hydrogen, halo or independently selected from the groups defined for R, R¹, R², R³, R⁴, R⁵ and R⁶ are independently hydrogen, alkyl of 1 to 10 carbon atoms, cycloalkyl of 6 to 10 carbon atoms, aryl of 6 to 14 carbon atoms or halo groups, provided that R′ is not hydrogen when R is alkyl as defined above, and further provided that when R and R′ are both either n-butyl, t-butyl or alkyl-substituted phenyl, at least one of R¹, R², R³, R⁴, R⁵ and R⁶ is alkyl, cycloalkyl, aryl or halo as defined above.

  描述了一种具有一个或多个取代基的亲脂性1,10-菲啰啉化合物。这些化合物具有以下结构：其中，R选自分子量至少为45的烷基、环烷基（环中有5至10个碳原子）和取代苯基的群组，R'为氢、卤素或独立选择为R定义的群组，R¹、R²、R³、R⁴、R⁵和R⁶独立地为氢、1至10个碳原子的烷基、6至10个碳原子的环烷基、6至14个碳原子的芳基或卤素基，但当R为上述定义的烷基时，R'不为氢；而且当R和R'均为正丁基、叔丁基或烷基取代的苯基时，R¹、R²、R³、R⁴、R⁵和R⁶中至少有一个为上述定义的烷基、环烷基、芳基或卤素。
• Production of aromatic amines
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0426536A1

  公开（公告）日：1991-05-08

  Aminoanthraquinones which are materials for dyes are prepared by allowing nitroanthraquinones to react with carbon monoxide and water in a liquid phase in the presence of a homogeneous catalyst comprising rhodium compounds or ruthenium compounds and solvents therefor.

  制备用作染料原料的氨基蒽醌的方法是，在由铑化合物或钌化合物组成的均相催化剂和溶剂存在下，使硝基蒽醌与一氧化碳和水在液相中发生反应。
• Process for the preparation of secondary amines
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0541176A2

  公开（公告）日：1993-05-12

  The invention provides a process for the preparation of a secondary amine which comprises reacting carbon monoxide, hydrogen, a polyolefin and a primary amine derivative having a terminal -NH₂ group and a terminal -NR¹R² group, wherein each of R¹ and R² independently represents a hydrogen atom or an alkyl group; in the presence of a suitable solvent and a catalyst system comprising a source of cationic rhodium; optionally a source of cationic ruthenium; an aromatic N-heterocyclic ligand and a source of an anion other than a halide.

  本发明提供了一种制备仲胺的工艺，该工艺包括使一氧化碳、氢气、聚烯烃 和具有末端-NH₂基团和末端-NR¹R²基团的伯胺衍生物（其中 R¹ 和 R² 各自独立地代表氢原子或烷基）反应；在合适的溶剂和催化剂体系存在下，催化剂体系包括阳离子铑源；阳离子钌源；芳香族 N-杂环配体和非卤化物阴离子源。
• Process for the preparation of a secondary amine and catalysts therefor
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0457386B1

  公开（公告）日：1994-12-14
• Process for catalytically reducing nitroaromatic compounds
  申请人：Montedison S.p.A.

  公开号：EP0097592B1

  公开（公告）日：1986-12-10