6-isopropyl-3-methylene-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-isopropyl-3-methylene-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: 5-methylidene-3-phenyl-2-propan-2-yl-2H-1,4-oxazin-6-one
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: BKQMENPDYFZLRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 6-isopropyl-3-methylene-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one 以 甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Asymmetric synthesis of bicyclic α-amino acids by a Diels–Alder reaction to a new chiral α,β-didehydroalanine derivative

  摘要：

  A new chiral cyclic alpha,beta-didehydroalanine derivative, (6S)-6-isopropyl-3-methylene-5-phenyl-3,6,dihydro-2H-1,4-oxazin-2-one, has been prepared by in situ aminomethylation-elimination of a chiral glycine-derived precursor. This oxazin-2-one acts as a reactive dienophile ire highly diastereoselective Diels-Alder reactions with cyclopenta- and cyclohexadiene. The major cycloadducts have been isolated and hydrolyzed to afford enantiomerically pure (-)-endo-2-aminobicyclo[2.2.1]heptane-2- and exo-2-aminobicyclo[2.2.2]octane-2-carboxylic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00061-0
• 作为产物：
  描述：

  2-溴-3-甲基-1-苯基丁酮 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 6-isopropyl-3-methylene-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of bicyclic α-amino acids by a Diels–Alder reaction to a new chiral α,β-didehydroalanine derivative

  摘要：

  A new chiral cyclic alpha,beta-didehydroalanine derivative, (6S)-6-isopropyl-3-methylene-5-phenyl-3,6,dihydro-2H-1,4-oxazin-2-one, has been prepared by in situ aminomethylation-elimination of a chiral glycine-derived precursor. This oxazin-2-one acts as a reactive dienophile ire highly diastereoselective Diels-Alder reactions with cyclopenta- and cyclohexadiene. The major cycloadducts have been isolated and hydrolyzed to afford enantiomerically pure (-)-endo-2-aminobicyclo[2.2.1]heptane-2- and exo-2-aminobicyclo[2.2.2]octane-2-carboxylic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00061-0

文献信息

• Asymmetric synthesis of bicyclic α-amino acids by a Diels–Alder reaction to a new chiral α,β-didehydroalanine derivative
  作者：Rafael Chinchilla、Larry R Falvello、Nuria Galindo、Carmen Nájera

  DOI：10.1016/s0957-4166(99)00061-0

  日期：1999.3

  A new chiral cyclic alpha,beta-didehydroalanine derivative, (6S)-6-isopropyl-3-methylene-5-phenyl-3,6,dihydro-2H-1,4-oxazin-2-one, has been prepared by in situ aminomethylation-elimination of a chiral glycine-derived precursor. This oxazin-2-one acts as a reactive dienophile ire highly diastereoselective Diels-Alder reactions with cyclopenta- and cyclohexadiene. The major cycloadducts have been isolated and hydrolyzed to afford enantiomerically pure (-)-endo-2-aminobicyclo[2.2.1]heptane-2- and exo-2-aminobicyclo[2.2.2]octane-2-carboxylic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.