(1R,5R,7S)-1,7-dimethyl-5-phenyl-3-propan-2-yl-6-oxa-3-azabicyclo[3.1.1]heptane-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (1R,5R,7S)-1,7-dimethyl-5-phenyl-3-propan-2-yl-6-oxa-3-azabicyclo[3.1.1]heptane-2,4-dione
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: ZGOLVZDBHVIUMF-IUIKQTSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,5R,7S)-1,7-dimethyl-5-phenyl-3-propan-2-yl-6-oxa-3-azabicyclo[3.1.1]heptane-2,4-dione 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以90%的产率得到(1R,5R,7R)-5,7-dimethyl-1-phenyl-3-propan-2-yl-4-sulfanylidene-6-oxa-3-azabicyclo[3.1.1]heptan-2-one
  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 生成 (1R,5R,7S)-1,7-dimethyl-5-phenyl-3-propan-2-yl-6-oxa-3-azabicyclo[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

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.