3-cis-Anilino-1-(4-methoxy-phenyl)-propen-(2)-on-(1) | 22292-84-8

• 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: 3-cis-Anilino-1-(4-methoxy-phenyl)-propen-(2)-on-(1)
• 英文别名: (2Z)-1-(4-methoxyphenyl)-3-(phenylamino)prop-2-en-1-one；(Z)-3-anilino-1-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 22292-84-8
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: MVQOSHNIGYVUGB-QXMHVHEDSA-N

物化性质

• 熔点：
  159-160 °C(Solv: methanol (67-56-1))
• 沸点：
  407.6±45.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-二苯基-3-丁炔-2-醇 、 3-cis-Anilino-1-(4-methoxy-phenyl)-propen-(2)-on-(1) 在 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(4-methoxyphenyl)(6-methyl-1,4,6-triphenyl-1,6-dihydropyridin-3-yl)methanone
  参考文献：
  名称：

  路易斯酸与炔丙醇催化烯胺酮的环化反应：多取代1,2-二氢吡啶的区域选择性合成

  摘要：

  在温和的反应条件下，开发了高效的BF 3 ·Et 2 O催化烯胺酮与炔丙醇的级联反应。该方法提供了对多取代的1,2-二氢吡啶的区域选择性访问，收率好至极佳。

  DOI：

  10.1021/jo4005553
• 作为产物：
  描述：

  对甲氧基苯乙酮 在 potassium hydrogensulfate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 3-cis-Anilino-1-(4-methoxy-phenyl)-propen-(2)-on-(1)
  参考文献：
  名称：

  Devi; Dutta; Nongkhlaw, Journal of the Indian Chemical Society, 2010, vol. 87, # 6, p. 739 - 742

  摘要：

  DOI：

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.
• Dutta, Milan Chandra; Chanda, Kaushik; Karim, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 11, p. 2471 - 2474
  作者：Dutta, Milan Chandra、Chanda, Kaushik、Karim、Vishwakarma

  DOI：——

  日期：——