(1R,2S,8S)-1,5,11,11-Tetramethyl-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-6-en-4-one | 1059607-22-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,8S)-1,5,11,11-Tetramethyl-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-6-en-4-one
• CAS: 1059607-22-5
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: FQGPPONVHDEADI-OXKLTCJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (1R,2S,8S)-1,5,11,11-Tetramethyl-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-6-en-4-one 、 3-溴丙烯 在 正丁基锂 、 二异丙胺 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.5h， 以93%的产率得到(1R,2S,5R,8S)-5-allyl-1,5,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one
  参考文献：
  名称：

  Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids by Diastereoselective Alkylation of Camphor-Based Tricyclic Iminolactone

  摘要：

  A novel and convenient route for the preparation of chiral tricyclic iminolactones 9 and 10 from camphorquinone has been developed. Alkylation of iminolactones 9 and 10 provided iminolactones 16 and 17 in high yields which were, in turn, alkylated again to afford the alpha,alpha-disubstituted products in good yields (70-90%) and excellent diastereoselectivities (> 98%). Hydrolysis of the alkylated iminolactones furnished the desired alpha,alpha-disubstituted alpha-amino acids in good yields and high enantiomeric excesses with good recovery yields of the chiral auxiliary 12 and 13. The extremely high endo-face selectivity for alkylation is discussed using semiempirical (MOPAC 93) calculations.

  DOI：

  10.1021/jo052435g
• 作为产物：
  描述：

  (1R,2S,8S)-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one 、 碘甲烷 在 lithium diisopropyl amide 、 N,N-二甲基丙烯基脲 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(1R,2S,8S)-1,5,11,11-Tetramethyl-3-oxa-6-aza-tricyclo[6.2.1.02,7]undec-6-en-4-one
  参考文献：
  名称：

  A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

  摘要：

  An efficient synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved via the shortest route at present. At the same time, 2-epiconagenin was synthesized according to the same methodology. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.033