(Z)-1-(4-nitrophenyl)-3-(phenylamino)prop-2-en-1-one | 60390-90-1

• 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: (Z)-1-(4-nitrophenyl)-3-(phenylamino)prop-2-en-1-one
• 英文别名: (Z)-(2-anilino-vinyl) p-nitrophenyl ketone；cis-3-Anilino-4'-nitro-acrylophenon
• CAS: 60390-90-1
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: XEPJVBFWZDBXRT-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.24
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-1-(4-nitrophenyl)-3-(phenylamino)prop-2-en-1-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 S-methyl N-(3-p-nitrophenyl-3-oxo-propen-1-yl)-N,N'-diphenyl isothiourea
  参考文献：
  名称：

  REACTION OF ENAMINONES WITH THIACUMULENES

  摘要：

  Enaminones 2, easily prepared from the corresponding sodium salts of beta -ketoaldehydes 1 and hydrochlorides of primary amines, react with carbon disulfide/sodium hydride to give dithiocarbamates 3 after alkylation. In a similar way thiocarbamoylation yields isothioureas 4. The C-13 NMR parameters of 2, 3 and 4 show significant low- and high-field shifts of the C-1 and C-2 signals, respectively.

  DOI：

  10.1080/10426509808032471
• 作为产物：
  描述：

  1-(4-nitrophenyl)-3-N,N-dimethylamino-2-propen-1-one 、 苯胺 在 iron(III) chloride 、 水 作用下， 反应 2.0h， 以90%的产率得到(Z)-1-(4-nitrophenyl)-3-(phenylamino)prop-2-en-1-one
  参考文献：
  名称：

  Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions

  摘要：

  Highly stereoselective synthesis of Z-enaminones bearing reactive secondary amino group has been successfully performed in water using tertiary amino group functionalized enaminones under ambient conditions. An interesting promotion effect of water on the reaction via hydrolysis-dehydration condensation has been observed through a designed isotope labeling experiment. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.715712

文献信息

• 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.