3-benzylamino-1-(4-methylphenyl)-prop-2-en-1-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: 3-benzylamino-1-(4-methylphenyl)-prop-2-en-1-one
• 英文别名: 3-(Benzylamino)-1-(4-methylphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: RLIXHJSQTFTKAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-benzylamino-1-(4-methylphenyl)-prop-2-en-1-one 、 聚合甲醛 、 金刚烷胺 以 甲醇 为溶剂， 以91%的产率得到(3-(adamantan-1-yl)-1-benzyl-1,2,3,4-tetrahydropyrimidin-5-yl)(p-tolyl)methanone
  参考文献：
  名称：

  Novel tetrahydropyrimidine–adamantane hybrids as anti-inflammatory agents: synthesis, structure and biological evaluation

  摘要：

  A series of novel (3-((3s,5s,7s)-adamantan-1-yl)-1-alkyl/aralkyl/aryl-1,2,3,4-tetrahydroyrimidin-5-yl)(aryl)methanones (5a-j) has been synthesized by the reaction of 1-aryl-3-(alkyl/aralkyl/aryl)aminoprop-2-en-1-ones 3a-j, 1-adamantanamine 4 and formaldehyde under thermal conditions. The structures of the products (5a-j) have been established with the help of spectral and analytical data. The stereochemistry of the products was established by X-ray crystallographic studies of a representative product (3-((3s,5s,7s)-adamantan-1-yl)-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)(4-chlorophenyl) methanone (5g) of the series. The target adamantane-tetrahydropyrimidine hybrids 5a-j were evaluated for their anti-inflammatory activities as a result of which compounds 5e (R=C6H5CH2, Ar=C6H5), 5i (R=CH3, Ar=4-CH3C6H4), 5j (R=C6H5CH2, Ar=4-CH3C6H4) and 5g (R=CH3, Ar=4-ClC6H4 ) were found to exhibit excellent and promising anti-inflammatory activities.

  DOI：

  10.1007/s00044-015-1332-x
• 作为产物：
  描述：

  3-dimethylamino-1-(4-methyl-phenyl)-2-propen-1-one 、 苄胺 在 potassium hydrogensulfate 作用下， 以 水 为溶剂， 生成 3-benzylamino-1-(4-methylphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  Novel tetrahydropyrimidine–adamantane hybrids as anti-inflammatory agents: synthesis, structure and biological evaluation

  摘要：

  A series of novel (3-((3s,5s,7s)-adamantan-1-yl)-1-alkyl/aralkyl/aryl-1,2,3,4-tetrahydroyrimidin-5-yl)(aryl)methanones (5a-j) has been synthesized by the reaction of 1-aryl-3-(alkyl/aralkyl/aryl)aminoprop-2-en-1-ones 3a-j, 1-adamantanamine 4 and formaldehyde under thermal conditions. The structures of the products (5a-j) have been established with the help of spectral and analytical data. The stereochemistry of the products was established by X-ray crystallographic studies of a representative product (3-((3s,5s,7s)-adamantan-1-yl)-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)(4-chlorophenyl) methanone (5g) of the series. The target adamantane-tetrahydropyrimidine hybrids 5a-j were evaluated for their anti-inflammatory activities as a result of which compounds 5e (R=C6H5CH2, Ar=C6H5), 5i (R=CH3, Ar=4-CH3C6H4), 5j (R=C6H5CH2, Ar=4-CH3C6H4) and 5g (R=CH3, Ar=4-ClC6H4 ) were found to exhibit excellent and promising anti-inflammatory activities.

  DOI：

  10.1007/s00044-015-1332-x

文献信息

• The α-Effect in Reactions of sp-Hybridized Carbon Atom:  Michael-Type Reactions of 1-Aryl-2-propyn-1-ones with Primary Amines
  作者：Ik-Hwan Um、Eun-Ju Lee、Jin-Ah Seok、Kyung-Hee Kim

  DOI：10.1021/jo050624t

  日期：2005.9.1

  mechanism. The α-effect increases as the substituent X in the phenyl ring of 2a−f becomes a stronger electron-donating group. However, the magnitude of the α-effect for the reactions of 2a−f is small (e.g., kNhydrazine/kNglycylglycine = 4.6−13) regardless of the electronic nature of the substituent X. The small βnuc has been suggested to be responsible for the small α-effect. A solvent kinetic isotope

  测量了1-（X-取代苯基）-2-丙炔-1-酮（2a - f）与一系列伯胺在H 2 O中的迈克尔型反应的二级速率常数（k N）在25.0±0.1°C下。对于1-苯基-2-丙炔-1-酮（2c）与非α-亲核胺的反应，获得了具有小的βnuc值（βnuc = 0.30）的线性布朗斯台德型图。肼比其他类似碱度的伯胺（例如，甘氨酰甘氨酸和甘氨酸乙酯）具有更高的反应活性，并且与线性布朗斯台德图呈正偏差。2a - f的反应与肼的化合物表现出线性的Hammett图，而与非α-亲核胺的化合物表现出线性的Yukawa-Tsuno图，表明取代基X的电子性质不影响反应机理。随着2a - f的苯环中的取代基X变为更强的供电子基团，α效应会增加。然而，为的反应中α-效果的大小2A - ˚F是小的（例如，ķ Ñ肼/ ķ Ñ甘氨酰甘氨酸= 4.6-13），而不管该取代基X的小β的电子性质的NUC有人认为这是造成小的α效应的原
• Novel tetrahydropyrimidine–adamantane hybrids as anti-inflammatory agents: synthesis, structure and biological evaluation
  作者：Utpalparna Kalita、Shunan Kaping、Revinus Nongkynrih、Laishram Indira Singha、Jai Narain Vishwakarma

  DOI：10.1007/s00044-015-1332-x

  日期：2015.6

  A series of novel (3-((3s,5s,7s)-adamantan-1-yl)-1-alkyl/aralkyl/aryl-1,2,3,4-tetrahydroyrimidin-5-yl)(aryl)methanones (5a-j) has been synthesized by the reaction of 1-aryl-3-(alkyl/aralkyl/aryl)aminoprop-2-en-1-ones 3a-j, 1-adamantanamine 4 and formaldehyde under thermal conditions. The structures of the products (5a-j) have been established with the help of spectral and analytical data. The stereochemistry of the products was established by X-ray crystallographic studies of a representative product (3-((3s,5s,7s)-adamantan-1-yl)-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)(4-chlorophenyl) methanone (5g) of the series. The target adamantane-tetrahydropyrimidine hybrids 5a-j were evaluated for their anti-inflammatory activities as a result of which compounds 5e (R=C6H5CH2, Ar=C6H5), 5i (R=CH3, Ar=4-CH3C6H4), 5j (R=C6H5CH2, Ar=4-CH3C6H4) and 5g (R=CH3, Ar=4-ClC6H4 ) were found to exhibit excellent and promising anti-inflammatory activities.