(1S,2R,6S,7R,exo)-3-oxa-5-aza-7-ethyl10.10-dimethyltricyclo<5.2.1.02,6>decan-4-one | 175917-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,2R,6S,7R,exo)-3-oxa-5-aza-7-ethyl10.10-dimethyltricyclo<5.2.1.02,6>decan-4-one
• 英文别名: (1S,2R,6S,7R,exo)-3-oxa-5-aza-7-ethyl10.10-dimethyltricyclo<5.2.1.0^2,6>decan-4-one
• CAS: 175917-13-2
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: PMUDSHUSYQOCPV-HNBLOZHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,6S,7R,exo)-3-oxa-5-aza-7-ethyl10.10-dimethyltricyclo<5.2.1.02,6>decan-4-one 在 diethylzinc 、 氯化二乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.83h， 生成 (1S,2R,6S,7R,exo)-N-((3'R,4'S,6'R)-bicyclo<2.2.1>heptene-4'-carbonyl)-3-oxa-5-aza-7ethyl-10,10-dimethyltricyclo<5.2.1.0^2,6>decan-4-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries

  摘要：

  Transposition of the dormant methyl group from C-1 in chiral oxazolidin-2-one 2 to C-7 in a six step synthetic sequence from (1R)-camphor 5 creates a novel transfigomer 4 with sufficient pi-topological bias to induce excellent levels of asymmetric induction in Lewis-acid catalysed Diels-Alder reactions of its alpha,beta-unsaturated carboximide derivatives with cyclopentadiene. Further modification of 4 by replacement of the C-7 methyl group with an ethyl substituent raises the level of diastereoselectivity for the acrylate derivative 11a from 81 to >95% d.e..

  DOI：

  10.1016/s0040-4020(96)00070-1
• 作为产物：
  描述：

  (1R,3R,exo)-3-hydroxy-1-ethyl-7,7-dimethylbicyclo<2.2.1>heptan-2-one 在 palladium on activated charcoal titanium(IV) isopropylate 、 sodium hydroxide 、 乙二醇二甲醚 、 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 73.5h， 生成 (1S,2R,6S,7R,exo)-3-oxa-5-aza-7-ethyl10.10-dimethyltricyclo<5.2.1.02,6>decan-4-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries

  摘要：

  Transposition of the dormant methyl group from C-1 in chiral oxazolidin-2-one 2 to C-7 in a six step synthetic sequence from (1R)-camphor 5 creates a novel transfigomer 4 with sufficient pi-topological bias to induce excellent levels of asymmetric induction in Lewis-acid catalysed Diels-Alder reactions of its alpha,beta-unsaturated carboximide derivatives with cyclopentadiene. Further modification of 4 by replacement of the C-7 methyl group with an ethyl substituent raises the level of diastereoselectivity for the acrylate derivative 11a from 81 to >95% d.e..

  DOI：

  10.1016/s0040-4020(96)00070-1