α-benzamidocinnamamide | 70985-09-0

• 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: α-benzamidocinnamamide
• 英文别名: (Z)-2-benzoylamino-3-phenylprop-2-enamide；α-benzoylamino-trans-cinnamic acid amide；α-Benzoylamino-trans-zimtsaeure-amid；N-[(Z)-3-amino-3-oxo-1-phenylprop-1-en-2-yl]benzamide
• CAS: 70985-09-0
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: MWYUFCXZABNQKA-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 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：
  72.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-benzamidocinnamamide 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以16%的产率得到(4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one
  参考文献：
  名称：

  Derivatives of α,β-dehydro amino acids: III. Reaction of 4-arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones with hexamethyldisilazane

  摘要：

  4-Arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones reacted with hexamethyldisilazane in ethyl acetate, acetonitrile, or DMF at room temperature to give mainly 2-acylamino-3-arylmethylideneprop-2-enamides, whereas in boiling DMF the corresponding 4-arylmethylidene-4,5-dihydro-1H-imidazol-5-ones were formed. The reaction of 2-benzoylamino-3-phenylprop-2-enamide with hexamethyldisilazane also led to the formation of 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one, while its reaction with chlorotrimethylsilane afforded either a 1:1 mixture of 4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-one and 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one or only the latter, depending on the solvent.

  DOI：

  10.1134/s1070428007060127
• 作为产物：
  描述：

  (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one 在 氨 作用下， 生成 α-benzamidocinnamamide
  参考文献：
  名称：

  Rao, Ch. Chennakesava; Lalitha, Nagubandi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 1, p. 3

  摘要：

  DOI：

文献信息

• Asymmetric Hydrogenation with Chiral Aminophosphine–Rhodium Complexes and Chiral Recognition by Bisphosphine–Rhodium Complexes in the Asymmetric Hydrogenation of Olefins through the Chiral Helical Conformation of Phenyl Groups on the Phosphorus Atom
  作者：Ken-ichi Onuma、Tomiyasu Ito、Asao Nakamura

  DOI：10.1246/bcsj.53.2016

  日期：1980.7

  rhodium complex of (1R,2R)-1,2-bis(diphenylphosphinamino)cyclohexane by the N-methylation of the ligand in asymmetric hydrogenation has been described. From stereochemical considerations, the chiral helical conformation of the phenyl groups attached on the phosphorus in bisphosphine-rhodium complexes may be responsible for the induced chirality of the product of the hydrogenation. A complex with a left-handed

  据报道，α-酰基氨基肉桂酸与（1R,2R）-1,2-双（N-二苯基膦基-N-甲基氨基）环己烷的铑络合物的不对称氢化反应优先生成（S）-氨基酸。相反，已经发现对映体(R)-氨基酸是通过用(1R,2R)-1,2-双(二苯基膦氨基)环己烷的铑络合物氢化而获得的。已经描述了通过配体的 N-甲基化在不对称氢化中对 (1R,2R)-1,2-双（二苯基膦氨基）环己烷的铑配合物的立体选择性反转的研究。从立体化学的角度来看，双膦-铑配合物中与磷相连的苯基的手性螺旋构象可能是氢化产物诱导手性的原因。具有左旋螺旋的复合物将产生 (R)-氨基酸，具有右旋螺旋的复合物将产生 (S)-氨基酸。溶剂和基材结构的影响...
• Rao, Ch. Chennakesava; Lalitha, Nagubandi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 1, p. 3
  作者：Rao, Ch. Chennakesava、Lalitha, Nagubandi

  DOI：——

  日期：——
• CASEIN KINASE 1delta (CK 1delta) INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES SUCH AS TAUOPATHIES
  申请人：Electrophoretics Limited

  公开号：US20160354375A1

  公开（公告）日：2016-12-08

  The invention relates to pharmaceutical compositions comprising casein kinase 1 delta (CK1δ) and to the use of said inhibitors in the treatment of neurodegenerative disorders such as Alzheimer's disease.
• Derivatives of α,β-dehydro amino acids: III. Reaction of 4-arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones with hexamethyldisilazane
  作者：V. O. Topuzyan、L. G. Arutyunyan、A. A. Oganesyan

  DOI：10.1134/s1070428007060127

  日期：2007.6

  4-Arylmethylidene-4,5-dihydro-1,3-oxazol-5-ones reacted with hexamethyldisilazane in ethyl acetate, acetonitrile, or DMF at room temperature to give mainly 2-acylamino-3-arylmethylideneprop-2-enamides, whereas in boiling DMF the corresponding 4-arylmethylidene-4,5-dihydro-1H-imidazol-5-ones were formed. The reaction of 2-benzoylamino-3-phenylprop-2-enamide with hexamethyldisilazane also led to the formation of 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one, while its reaction with chlorotrimethylsilane afforded either a 1:1 mixture of 4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-one and 4-benzylidene-2-phenyl-4,5-dihydro-1H-imidazol-5-one or only the latter, depending on the solvent.
• A Practical and Efficient Synthesis of 2,5-Disubstituted-3,5-dihydro-imidazol-4-ones from Oxazolones
  作者：Flavio Chavez、Caslin Pavy、Thomas Williamson、Thomas Cleary

  DOI：10.1080/00397911.2011.581406

  日期：2012.11.15

  An alternative procedure for the synthesis of 2,5-disubstituted-3,5-dihydro-imidazol-4-ones from substituted oxazolones was evaluated. The initial oxazolone ring-opening reaction was examined with a variety of ammonia source compounds followed by the subsequent 3,5-dihydro-imidazol-4-one cyclization reaction, which was carried out with either an organic or inorganic base in aprotic solvents. In this article, we report the results of an efficient and straightforward procedure for the synthesis of 2,5-disubstituted-3,5-dihydro-imidazol-4-ones that gives satisfactory yield and quality.