(1S,2R,5S,8R)-5-allyl-5-benzyl-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one

• 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: (1S,2R,5S,8R)-5-allyl-5-benzyl-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one
• 英文别名: (1S,2R,5S,8R)-5-benzyl-8,11,11-trimethyl-5-prop-2-enyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one
• 化学式: C₂₂H₂₇NO₂
• 分子量: 337.462
• InChiKey: BCCSXICPVRMMFN-YAKVFXAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R)-(-)-樟脑醌 在 sodium tetrahydroborate 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 59.5h， 生成 (1S,2R,5S,8R)-5-allyl-5-benzyl-8,11,11-trimethyl-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