(Z)-4-(2,6-dimethylphenylamino)pent-3-en-2-one

• 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: (Z)-4-(2,6-dimethylphenylamino)pent-3-en-2-one
• 英文别名: (Z)-4-(2,6-dimethylanilino)pent-3-en-2-one
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: BIWBESSJGCEQJK-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Hf(NMe₂)₄ 、 (Z)-4-(2,6-dimethylphenylamino)pent-3-en-2-one 以 甲苯 为溶剂， 反应 16.0h， 以52%的产率得到bis[(Z)-4-(2,6-dimethylphenylamino)pent-3-en-2-one]bis(dimethylamido)hafnium(IV)
  参考文献：
  名称：

  Synthesis of hafnium(IV) β-ketoiminates as potential precursors for the MOCVD of HfO2

  摘要：

  An amine-elimination pathway has been used to produce two new hafnium compounds starting from the tetrakis(dimethylamido)hafnium(IV) complex and an amine - bis[(Z)-4-(2,6-dimethylphenylamino)pent-3-en-2-one]bis(dimethylamido)hafnium(IV) and [(Z)-4-(4-methylphenylamino)pent-3-en-2-one]bis(dimethylamido)hafnium(IV). The resulting complexes were characterized by single crystal X-ray diffraction and NMR. In addition, their volatilities were studied by thermogravimetric analysis (TGA), where [(Z)-4-(4-methylphenylamino)pent-3-en-2-one]bis(dimethylamido)hafnium(IV) showed better properties for MOCVD applications with a Delta H-sub of 27 kJ/mol and a T-sub of 104 degrees C. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.10.002
• 作为产物：
  描述：

  2,6-二甲基苯胺 、 乙酰丙酮 在 溶剂黄146 作用下， 反应 1.25h， 以80%的产率得到(Z)-4-(2,6-dimethylphenylamino)pent-3-en-2-one
  参考文献：
  名称：

  K7[PW11CoO40]：用于β-二羰基化合物烯化的高效环保催化剂

  摘要：

  摘要 在催化量的 K7[PW11CoO40] 存在下，多种 β-二羰基化合物与伯胺和仲胺的缩合反应。从该反应中以高产率获得了 N-取代的 β-烯氨基酯和酮。

  DOI：

  10.1080/00397910701860968

文献信息

• K₇[PW₁₁CoO₄₀]: Efficient and Ecofriendly Catalyst for the Enamination of β-Dicarbonyl Compounds
  作者：Hossein A. Oskooie、Majid M. Heravi、Negar M. Javadi、Khadijeh Bakhtiari、Fatemeh F. Bamoharram

  DOI：10.1080/00397910701860968

  日期：2008.8.18

  Abstract Condensation of a variety of β-dicarbonyl compounds with primary and secondary amines carried out in the presence of catalytic amounts of K7[PW11CoO40]. From this reaction N-substituted β-enamino esters and ketones were obtained in high yields.

  摘要 在催化量的 K7[PW11CoO40] 存在下，多种 β-二羰基化合物与伯胺和仲胺的缩合反应。从该反应中以高产率获得了 N-取代的 β-烯氨基酯和酮。
• Deuterium Isotope Effects on 13C Chemical Shifts of Enaminones.
  作者：Donka Kh. Zheglova、Daniel G. Genov、Simon Bolvig、Poul Erik Hansen、M. Hanfland、E. Dooryhee

  DOI：10.3891/acta.chem.scand.51-1016

  日期：——

  Deuterium isotope effects on C-13 chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, (2) Delta C-1(ND). Methyl-substitution al C-l leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between (2) Delta C-1(ND) and (3) Delta C-2'(ND). The latter becomes negative in the sterically hindered cases. (3) Delta C-2'(ND) may therefore be used as a gauge of the twist of the phenyl ring.o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller (2) Delta C-2(ND) and (2) Delta C-2 ''(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer (2) Delta C(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, (2) Delta C(OD), isotope effects.
• Formic Acid: A Low-Cost, Mild, Ecofriendly, and Highly Efficient Catalyst for the Rapid Synthesis of <font>β</font>-Enaminones
  作者：Siddappa A. Patil、Phillip A. Medina、Diego Gonzalez-Flores、Jason K. Vohs、Seth Dever、Leslie W. Pineda、Mavis L. Montero、Bradley D. Fahlman

  DOI：10.1080/00397911.2012.708467

  日期：2013.9.2

  -Enaminones have been synthesized by the condensation reaction of -diketones with various anilines in the presence of a catalytic amount of formic acid, mild and highly efficient acid catalyst in methanol. These condensation reactions proceed smoothly in short reaction times with near-quantitative yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• Synthesis, structure and ethylene polymerization behavior of zirconium complexes with chelating ketoiminate ligands
  作者：Jindong Kim、Jeong-Wook Hwang、Youngjo Kim、Min Hyung Lee、Yonggyu Han、Youngkyu Do

  DOI：10.1016/s0022-328x(00)00555-6

  日期：2001.2

  Mixed ketoiminate/ketoimine/pentamethylcyclopentadienyl (Cp*) complex of zirconium, [(eta (5)-Cp*)CH3C(O)CHC-(NHR)CH3} CH3C(O)CHC(NR)CH3}ZrCl2] (R = 4-CF3Ph) (3) has been prepared in high yield by the reaction of one equivalent of 4-CF3-phenyl-beta -ketoimine (1a) and one equivalent of lithium 4-CF3-phenyl-beta -ketoiminate (2a) with one equivalent of Cp*ZrCl3 in Et2O. Bis(ketoiminate)zirconium dichloride complexes, 4 and 6, have been also prepared in high yield by the reaction of amine elimination of ketoimine ligands, respectively 1a and 1b, with Zr(NMe2)(4) and followed by chlorination reaction with TMSCl. The X-ray crystallography reveals that the compound 3 is based on distorted octahedral geometry containing a ketoimine and a ketoiminate. The ketoiminate ligand coordinates to the zirconium as a bidentate ligand, leaving the metal center coordinatively unsaturated and thus leading to an additional binding of a ketoimine ligand to the metal to stabilize the complex 3. The zirconium complexes 3, 4 and 6 provide the moderate activity for the polymerization of ethylene in the presence of MMAO cocatalyst. Low molecular weight and high density polyethylene was obtained. (C) 2001 Elsevier Science B.V. All rights reserved.
• A simple protocol for the preparation of β-enamino ketones catalyzed by NbOPO4 under solvent free conditions
  作者：Felipe Wodtke、Fernando R. Xavier、Samuel R. Mendes、Alfredo R.M. de Oliveira、Rogério A. Gariani

  DOI：10.1016/j.tetlet.2016.12.019

  日期：2017.1

  A novel application of the highly stable niobium oxide phosphate (NbOPO4) as an efficient catalyst for the synthesis of beta-enamino ketones under solvent-free conditions is described. This protocol, exhibits attractive yields, short reaction periods, lower loading of catalyst and high chemoselectivity. (C) 2016 Elsevier Ltd. All rights reserved.