N-benzyl-N-tigloylbenzoylformamide | 194023-05-7

• 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: N-benzyl-N-tigloylbenzoylformamide
• 英文别名: (E)-N-benzyl-2-methyl-N-(2-oxo-2-phenylacetyl)but-2-enamide
• CAS: 194023-05-7
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: DERNZBWIJJBIOA-CRKCGEKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-tigloylbenzoylformamide 以 苯 为溶剂， 生成 (1R,5R,7S)-3-Benzyl-1,7-dimethyl-5-phenyl-6-oxa-3-aza-bicyclo[3.1.1]heptane-2,4-dione 、 (1R,5R,7R)-3-Benzyl-1,7-dimethyl-5-phenyl-6-oxa-3-aza-bicyclo[3.1.1]heptane-2,4-dione
  参考文献：
  名称：

  Solid State Photochemical Reaction of N-(α,β-Unsaturated carbonyl)benzoylformamides

  摘要：

  Photochemical reactions of various N-(alpha,beta-unsaturated carbonyl)benzoylfomamides both in solution and in a solid state were investigated. Under homogeneous conditions, all acyclic imides underwent photochemical 2 + 2 cycloaddition that resulted in the production of bicyclic oxetanes. N-Isopropyl- and N-benzyl-N-tigloylbenzoylformamides crystallized in a chiral space group, and the photolysis in the solid state yielded corresponding optic ally-active oxetanes. N-Tigloylbenzoylformanilide underwent cis-trans isomerization to yield a photostationary state (cis/trans = 1.3). Solid state oxetane formation of N-benzyl- and N-(o-tolyl)- and N-(2,6-xylpl)-N-tigloylbenzoylformamides progressed via the crystal-to-crystal pathway which was followed by X-ray powder diffraction, N-Benzyl-N-methacryloylbenzoylformamide crystallized in a chiral space group, and the solid state reaction led to an optically active beta-lactam via topochemically-controlled hydrogen abstraction by the alkenyl carbon atom. Photolysis of N-isopropyl-N-methacryloylbenzoylformamide in the solid state led to both oxetane formation and a transformation to azetidine-2,4-dione involving a 1,5-benzoyl shift.

  DOI：

  10.1021/jo9704974
• 作为产物：
  描述：

  氧代(苯基)乙酰氯 、 (E)-N-benzyl-2-methylbut-2-enamide 以80%的产率得到N-benzyl-N-tigloylbenzoylformamide
  参考文献：
  名称：

  Solid State Photochemical Reaction of N-(α,β-Unsaturated carbonyl)benzoylformamides

  摘要：

  Photochemical reactions of various N-(alpha,beta-unsaturated carbonyl)benzoylfomamides both in solution and in a solid state were investigated. Under homogeneous conditions, all acyclic imides underwent photochemical 2 + 2 cycloaddition that resulted in the production of bicyclic oxetanes. N-Isopropyl- and N-benzyl-N-tigloylbenzoylformamides crystallized in a chiral space group, and the photolysis in the solid state yielded corresponding optic ally-active oxetanes. N-Tigloylbenzoylformanilide underwent cis-trans isomerization to yield a photostationary state (cis/trans = 1.3). Solid state oxetane formation of N-benzyl- and N-(o-tolyl)- and N-(2,6-xylpl)-N-tigloylbenzoylformamides progressed via the crystal-to-crystal pathway which was followed by X-ray powder diffraction, N-Benzyl-N-methacryloylbenzoylformamide crystallized in a chiral space group, and the solid state reaction led to an optically active beta-lactam via topochemically-controlled hydrogen abstraction by the alkenyl carbon atom. Photolysis of N-isopropyl-N-methacryloylbenzoylformamide in the solid state led to both oxetane formation and a transformation to azetidine-2,4-dione involving a 1,5-benzoyl shift.

  DOI：

  10.1021/jo9704974

文献信息

• Solid State Photochemical Reaction of <i>N</i>-(α,β-Unsaturated carbonyl)benzoylformamides
  作者：Masami Sakamoto、Masaki Takahashi、Tsutomu Fujita、Shoji Watanabe、Takehiko Nishio、Ikuo Iida、Hiromu Aoyama

  DOI：10.1021/jo9704974

  日期：1997.9.1

  Photochemical reactions of various N-(alpha,beta-unsaturated carbonyl)benzoylfomamides both in solution and in a solid state were investigated. Under homogeneous conditions, all acyclic imides underwent photochemical 2 + 2 cycloaddition that resulted in the production of bicyclic oxetanes. N-Isopropyl- and N-benzyl-N-tigloylbenzoylformamides crystallized in a chiral space group, and the photolysis in the solid state yielded corresponding optic ally-active oxetanes. N-Tigloylbenzoylformanilide underwent cis-trans isomerization to yield a photostationary state (cis/trans = 1.3). Solid state oxetane formation of N-benzyl- and N-(o-tolyl)- and N-(2,6-xylpl)-N-tigloylbenzoylformamides progressed via the crystal-to-crystal pathway which was followed by X-ray powder diffraction, N-Benzyl-N-methacryloylbenzoylformamide crystallized in a chiral space group, and the solid state reaction led to an optically active beta-lactam via topochemically-controlled hydrogen abstraction by the alkenyl carbon atom. Photolysis of N-isopropyl-N-methacryloylbenzoylformamide in the solid state led to both oxetane formation and a transformation to azetidine-2,4-dione involving a 1,5-benzoyl shift.