p-xylylaminomethylferrocene | 252651-13-1

• 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: p-xylylaminomethylferrocene
• 英文别名: [(η5-cyclopentadienyl)Fe(η5-C5H5CH2NHCH2C6H4CH3-4)]；cyclopenta-1,3-diene;1-cyclopenta-1,3-dien-1-yl-N-[(4-methylphenyl)methyl]methanamine;iron(2+)
• CAS: 252651-13-1
• 化学式: C₁₉H₂₁FeN
• 分子量: 319.229
• InChiKey: DUXZGRONTSEABB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 p-xylylaminomethylferrocene 在 sodium cyanoborohydride 作用下， 以 水 、 溶剂黄146 为溶剂， 以80%的产率得到[(η5-cyclopentadienyl)Fe(η5-C5H4CH2N(CH3)CH2C6H4CH3-4)]
  参考文献：
  名称：

  Activation of the CH bond in [(η5-C5H5)Fe(η5-C5H4CH2N(CH3)CH2C6H4R-4)] induced by platinum (II): Crystal structure of σ-Pt[(η5-C5H5)Fe(η5-C5H3CH2N(CH3)CH2C6H4OCH3-4)]Cl(DMSO)

  摘要：

  Condensations of ferrocenylcarboxaldehyde (1) and p-methyl (2b) or p-chlorobenzylamines (2d) in methanol resulted in ferrocenylaldimines 3b, d which were reduced by lithium aluminum hydride to give 4b, d, respectively. Reductive methylations of 4b, d with aqueous formaldehyde, sodium cyanoborohydride and acetic acid afforded the tertiary ferrocenylamines 5b, d. Treatment of 5a-e [(eta(5)-C5H5)Fe(eta(5)-C5H4CH2N(CH3)CH2C6H4R-4)] (R = CH3O(a), CH3(b), H(c), Cl(d), NO2(e)) with cis-[Pt(DMSO)(2)Cl-2] in methanol produced predominately cycloplatinated complexes 6a-e sigma-Pt[(eta(5)-C5H5)Fe(eta(5)-C5H3CH2N(CH3)CH2C6H4-R-4)]Cl(DMSO) (R = same as before) in which the configurations consisted of RNRP and SNSP, In addition, the preferred activation of the C-H bond in the cyclopentadienyl ring rather than that in the phenyl ring was also observed. All compounds 3b-5b, 3d-5d, 6a-e were characterized by elemental analysis, IR and H-1 NMR. The structure of 6a was determined by X-ray single crystal diffraction. The possible mechanism for the formation of 6 was discussed. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2006.02.017
• 作为产物：
  描述：

  4'-methylbenzyl-ferrocenylcarboxaldimine 、 lithium aluminium tetrahydride 以 四氢呋喃 为溶剂， 以80%的产率得到p-xylylaminomethylferrocene
  参考文献：
  名称：

  Activation of the CH bond in [(η5-C5H5)Fe(η5-C5H4CH2N(CH3)CH2C6H4R-4)] induced by platinum (II): Crystal structure of σ-Pt[(η5-C5H5)Fe(η5-C5H3CH2N(CH3)CH2C6H4OCH3-4)]Cl(DMSO)

  摘要：

  Condensations of ferrocenylcarboxaldehyde (1) and p-methyl (2b) or p-chlorobenzylamines (2d) in methanol resulted in ferrocenylaldimines 3b, d which were reduced by lithium aluminum hydride to give 4b, d, respectively. Reductive methylations of 4b, d with aqueous formaldehyde, sodium cyanoborohydride and acetic acid afforded the tertiary ferrocenylamines 5b, d. Treatment of 5a-e [(eta(5)-C5H5)Fe(eta(5)-C5H4CH2N(CH3)CH2C6H4R-4)] (R = CH3O(a), CH3(b), H(c), Cl(d), NO2(e)) with cis-[Pt(DMSO)(2)Cl-2] in methanol produced predominately cycloplatinated complexes 6a-e sigma-Pt[(eta(5)-C5H5)Fe(eta(5)-C5H3CH2N(CH3)CH2C6H4-R-4)]Cl(DMSO) (R = same as before) in which the configurations consisted of RNRP and SNSP, In addition, the preferred activation of the C-H bond in the cyclopentadienyl ring rather than that in the phenyl ring was also observed. All compounds 3b-5b, 3d-5d, 6a-e were characterized by elemental analysis, IR and H-1 NMR. The structure of 6a was determined by X-ray single crystal diffraction. The possible mechanism for the formation of 6 was discussed. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2006.02.017

文献信息

• Chemical and Electrochemical Formation of Pseudorotaxanes Composed of Alkyl(ferrocenylmethyl)ammmonium and Dibenzo[24]crown-8
  作者：Masaki Horie、Yuji Suzaki、Kohtaro Osakada

  DOI：10.1021/ic050215f

  日期：2005.8.1

  (1-hydroxy-2,2,6,6-tetramethylpiperidine) and DB24C8 affords the corresponding pseudorotaxanes. The ESR spectrum of the reaction mixture indicates the formation of a TEMPO radical in high yield. Details of the conversion of the dialkylamino group of the ligand to the dialkylammonium group are investigated by using a flow electrolysis method linked to spectroscopic measurements. The proposed mechanism

  对二甲苯基氨基甲基二茂铁（1）和正己基氨基甲基二茂铁（2）的HCl和NH（4）PF（6）质子化形成二茂铁基甲基（烷基）铵盐。二苯并[24]冠-8（DB24C8）包含该化合物可产生[2]假轮烷，[（DB24C8）（1-H）]（+）（PF（6））和[（DB24C8）（2-H） ]（+）（PF（6））。前一种产物的X射线衍射表明由轴和大环分子组成的互锁结构。观察到分子间的NH ... O和CH ... O相互作用以及芳族平面的堆积。[（DB24C8）（1-H）]（+）（PF（6））呈固态，通过红外光谱和元素分析表征。1,1'-双（对二甲苯基氨基甲基）二茂铁的类似反应（3）形成[2]和[3]假轮烷的混合物，[（DB24C8）（3-H（2））]（2 +）（ PF（6））（2）和[（DB24C8）（2）（3-H（2））]（2 +）（PF（6））（2）。分离具有两个DB24C8分子的后一种产物，并通过X
• Formation of Pseudorotaxane Induced by Electrochemical Oxidation of Ferrocene-Containing Axis Molecule in the Presence of Crown Ether
  作者：Masaki Horie、Yuji Suzaki、Kohtaro Osakada

  DOI：10.1021/ja039899l

  日期：2004.3.1

  The electrochemical oxidation of aminomethylferrocenes in the presence of dibenzo[24]crown-8 affords pseudorotaxanes containing a ferrocenyl group in its axis moiety. The formation of the pseudorotaxanes results from formation of secondary ammonium ions by rapid electron transfer from the N atom to the initially formed Fe(III) state, followed by hydrogen atom transfer from TEMPOH to the N+*.