6-amino-3-methyl-1-phenyl-4-azahept-2-en-1-one | 913196-60-8

• 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: 6-amino-3-methyl-1-phenyl-4-azahept-2-en-1-one
• 英文别名: 6-amino-3,6-dimethyl-1-phenyl-4-azahex-2-en-1-one；3-(2-amino-propylimino)-1-phenyl-butan-1-one；6-amino-3-methyl-1-phenyl-4-azahept-2-ene-1-one；6-amino-3-methyl-1-phenyl-4-aza-2-hepten-1-one；HAMPAH；HAMPAN；3-(2-Aminopropylamino)-1-phenylbut-2-en-1-one；3-(2-aminopropylamino)-1-phenylbut-2-en-1-one
• CAS: 913196-60-8
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: NGJGZXVLRWJYQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-[ReOCl3(PPh3)2] 、 6-amino-3-methyl-1-phenyl-4-azahept-2-en-1-one 以 丙酮 为溶剂， 以71%的产率得到[(μ-O)(ReOCl(6-amino-3-methyl-1-phenyl-4-azahept-2-ene-1-one(1-)))2]
  参考文献：
  名称：

  Coordination behaviour of acetylacetone-derived Schiff bases towards rhenium(I) and (V)

  摘要：

  The oxo-bridged dinuclear rhenium(V) complex [(mu-O)[ReOCl(amp)}(2)] (1) was prepared by the reaction of trans-[ReOCl3(PPh3)(2)] and 6-amino-3-methyl-1-phenyl-4-azahept-2-ene-1-one (Hamp) in acetone. The characterization of 1 by elemental analysis, infrared and H-1 NMR spectroscopy and X-ray crystallography shows that amp is coordinated as a monoanionic NNO-donor chelate as an amino-amido ketone. However, the reaction of the similar ligand 7-amino-4,7-dimethyl-5-aza-3-octen-2-one (Hada) with [Re(CO)(5)Br] produced fac-[Re(CO)(3)Br(Hada)], with Hada coordinated as a neutral bidentate N,N-donor amino-imino-ketone. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.01.036
• 作为产物：
  描述：

  1,2-丙二胺 、 1-苯基-1,3-丁二酮 以 氯仿 为溶剂， 生成 6-amino-3-methyl-1-phenyl-4-azahept-2-en-1-one 、 6-amino-3,5-dimethyl-1-phenyl-4-azahex-2-en-1-one
  参考文献：
  名称：

  四齿席夫碱配体的镍（II）和铜（II）配合物的合成与表征

  摘要：

  1,2-二氨基丙烷和1-苯基丁烷-1,3-二酮在高稀释度下的1：1缩合产生了齿状单缩合席夫碱6-氨基-3-甲基-1-苯基-的两个位置异构体的混合物4-氮杂-2-庚烯-1-酮（HAMPAH）和6-氨基-3,5-二甲基-1-苯基-4-氮杂-2-己烯-1-酮（HADPAH）。齿状配体的混合物已用于与吡啶-2-甲醛或2-乙酰基吡啶进一步缩合以获得不对称的四齿席夫碱配体。然后使四齿席夫碱分别与高氯酸铜（II）和镍（II）的甲醇溶液反应。X射线衍射证实了两种配合物的结构，并表明二胺与1-苯基丁烷-1，3-二酮的缩合位点是相同的。

  DOI：

  10.1016/j.ica.2010.10.010

文献信息

• Rare Example of μ-Nitrito-1κ²<i>O</i>,<i>O′</i>:2κ<i>O</i> Coordinating Mode in Copper(II) Nitrite Complexes with Monoanionic Tridentate Schiff Base Ligands: Structure, Magnetic, and Electrochemical Properties
  作者：Biswarup Sarkar、Sanjit Konar、Carlos J. Gómez-García、Ashutosh Ghosh

  DOI：10.1021/ic8011519

  日期：2008.12.15

  equatorial plane around Cu(II), whereas the second oxygen atom of the nitrite ligand coordinates to one of the axial positions. In 1, this axially coordinated oxygen atom of the nitrite ligand also coordinates weakly to the other axial position of a Cu(II) ion of another unit to form a one-dimensional chain with the mu-nitrito-1kappa(2)O,O':2kappaO bridging mode. Complexes 2 and 3 are discrete monomers that

  三个新的铜（II）配合物[CuL（1）（NO（2））]（n）（1），[CuL（2）（NO（2））]（2）和[CuL（3）（ NO（2））]（3），具有三个类似的三齿席夫碱配体[HL（1）= 6-氨基-3-甲基-1-苯基-4-氮杂庚-2-烯-1-一，HL（2 ）= 6-氨基-3-甲基-1-苯基-4-azahex-2-en-1-one，HL（3）= 6-二乙基氨基-3-甲基-1-苯基-4-azahex-2- [en-1-one]已经合成，并在结构和磁性上进行了表征。在所有三种配合物中，三齿席夫碱配体和亚硝酸根离子的一个氧原子构成围绕Cu（II）的赤道面，而亚硝酸根配体的第二个氧原子与轴向位置之一协调。在1中，亚硝酸根配体的这个轴向配位的氧原子也弱配位到另一个单元的Cu（II）离子的另一个轴向位置，与mu-nitrito-1kappa（2）O，O形成一维链' ：2kappO桥接模式。配合物2和3
• CuII acetate complexes involving N,N,O donor Schiff base ligands: Mono-atomic oxygen bridged dimers and alternating chains of the dimers and Cu2(OAc)4
  作者：Biswarup Sarkar、Michael G.B. Drew、Marta Estrader、Carmen Diaz、Ashutosh Ghosh

  DOI：10.1016/j.poly.2008.05.004

  日期：2008.8

  Two tridentate N,N,O donor Schiff bases, HL1 (4-(2-ethylamino-ethylimino)-pentan-2-one) and HL2 (3-(2-amino-propylimino)-1-phenyl-butan-1-one) on reaction with Cu-II acetate in presence of triethyl amine yielded two basal-apical, mono-atomic acetate oxygen-bridging dimeric copper(II) complexes, [Cu2L21(OAc)(2)] (1), [Cu2L22(OAc)(2)] (2). Whereas two other similar tridentate ligands HL3 (4-(2-amino-propylimino)-pentane-2-one) and HL3 (3-(2-amino-ethylimino)-1-phenyl-butan-1-one) under the same conditions produced a mixture of the corresponding dinners and a one-dimensional alternating chain of the dimer and copper acetate moiety, [Cu4L23(OAc)(6)](n) (3) and [Cu4L24(OAc)(6)](n) (4), formed by a very rare mu(3) bridging mode of the acetate ion. All four complexes (1-4) have been characterized by X-ray crystallography. The isotropic Hamiltonian, H = -JS(1)S(2) has been used to interpret the magnetic data. Magnetic measurements of 1 and 2 in the temperature range 2-300 K reveal a very weak antiferromagnetic coupling for both complexes U = -0.56 and -1.19 cm(-1) for 1 and 2, respectively). (C) 2008 Elsevier Ltd. All rights reserved.
• A novel copper(II) complex with a pendant Schiff base: An unprecedented monodentate bonding mode of the potentially tridentate ligand
  作者：Shouvik Chattopadhyay、Gabriele Bocelli、Andrea Cantoni、Ashutosh Ghosh

  DOI：10.1016/j.ica.2006.06.009

  日期：2006.10

  The 1:1 condensation of 1-benzoylacetone and 1,2-diaminopropane yields 6-amino-3-methyl-1-phenyl-4-azahept-2-en-1-one (HL). When copper(II) perchlorate is added to the methanolic solution of HL, followed by triethylamine in 1:2:1 molar ratio, an unusual copper(II) complex, [Cu(L)(HL)]ClO4, is separated out where the deprotonated ligand, L, is coordinated in the usual chelating tridentate manner but HL is coordinated to Cu(II) only through the amine N, i.e. it acts as a pendant ligand. The complex is characterized by X-ray crystal structure analysis. (c) 2006 Elsevier B.V. All rights reserved.
• Trinuclear Cu(II) complexes containing peripheral ketonic oxygen bridges and a μ3-OH core: Steric influence on their structures and existence
  作者：Biswarup Sarkar、Mau Sinha Ray、Michael G.B. Drew、Albert Figuerola、Carmen Diaz、Ashutosh Ghosh

  DOI：10.1016/j.poly.2006.05.032

  日期：2006.11

  Two tridentate Schiff bases, HL1(6-amino-3-methyl-1-phenyl-4-azahex-2-en-1-one), and HL2 (6-atnino-3,6-dimethyl-1-phenyl-4-azahex-2-en-1-one) on reaction with Cu(II) perchlorate in the presence of triethyl amine yielded two new trinuclear copper(II) complexes, [(CuL1)(3)(mu(3)-OH)](ClO4)(2) (1) and [(CuL2)(3)(mu(3)-OH)](ClO4)(2) center dot 0.75H(2)O (2), whereas another tridentate ligand HL3 (7-amino-3-methyl-1-phenyl-4-azahept-2-en-1-one) underwent hydrolysis under the same reaction conditions to result in the formation of a mononuclear complex, [Cu(bn)(pn)ClO4] (3) [where bn = 1-benzoylacetonate and pn = 1,3-propanediamine]. All three complexes have been characterized by X-ray crystallography. For both 1 and 2 the cationic part is trinuclear with a [Cu3OH] core held by three carbonyl oxygen bridges between each pair of copper(II) atoms. The structure of 3 is a monomer with a chelating 1,3-propanediamine and a benzoyl acetone moiety. Magnetic measurements of I and 2 have been performed in the 2-300 K temperature range. The experimental data could be satisfactorily reproduced by using an isotropic exchange model, H = -J(S1S2 + S2S3 + S1S3), yielding as best fit parameters: J = -25.6 cm(-1), g = 2.21 for 1 and J = 11.2 cm(-1), g = 2.10 for 2. The EPR spectra at low temperature could be indicative of spin frustration in complex 1. (C) 2006 Elsevier Ltd. All rights reserved.