(Z)-1-(2-hydroxyphenyl)-3-(phenylamino)prop-2-en-1-one | 35614-54-1

• 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-(2-hydroxyphenyl)-3-(phenylamino)prop-2-en-1-one
• 英文别名: (Z)-3-anilino-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 35614-54-1
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: LNNHGWYFYIQMEJ-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 、 苯胺 在 iron(III) chloride 、 水 作用下， 反应 2.0h， 以92%的产率得到(Z)-1-(2-hydroxyphenyl)-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

• Discovery of two new classes of potent monoamine oxidase-B inhibitors by tricky chemistry
  作者：F. Cagide、T. Silva、J. Reis、A. Gaspar、F. Borges、L. R. Gomes、J. N. Low

  DOI：10.1039/c4cc08798d

  日期：——

  The discovery of potent and selective monoamine oxidase-B inhibitors for the management of neurodegenerative diseases such as Alzheimer's and Parkinson's diseases is still a challenging endeavor. Herein, we report the discovery of two new classes of potent and selective MAO-B inhibitors based on chromane-2,4-dione and chromone-3-carboxamide scaffolds.

  发现用于治疗神经退行性疾病例如阿尔茨海默氏病和帕金森氏病的有效和选择性的单胺氧化酶-B抑制剂仍然是一项艰巨的任务。在本文中，我们报告发现了基于苯并二氢吡喃-2,4-二酮和苯并三苯甲酮-3-甲酰胺骨架的两类新的有效和选择性MAO-B抑制剂。
• 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.
• Heterocyclic Systems; 10¹. Defunctionalisation of 4-Oxo-4<i>H</i>-[1]benzopyran-3-carboxylic acids and -3-carboxaldehydes
  作者：Chandra Kanta Ghosh、Smriti Khan

  DOI：10.1055/s-1981-29574

  日期：——
• GHOSH, CH. K.;KHAN, S., SYNTHESIS, BRD, 1981, N 9, 719-721
  作者：GHOSH, CH. K.、KHAN, S.

  DOI：——

  日期：——
• Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions
  作者：Yunyun Liu、Rihui Zhou、Jie-Ping Wan

  DOI：10.1080/00397911.2012.715712

  日期：2013.9.17

  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.