(1S,2R,6S,7R,exo)-N-crotonoyl-3-oxa-5-aza-7-ethyl-10,10-dimethyltricyclo<5.2.1.0^2,6>decan-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,6S,7R,exo)-N-crotonoyl-3-oxa-5-aza-7-ethyl-10,10-dimethyltricyclo<5.2.1.0^2,6>decan-4-one
• 英文别名: (1S,2R,6S,7R)-5-[(E)-but-2-enoyl]-7-ethyl-10,10-dimethyl-3-oxa-5-azatricyclo[5.2.1.02,6]decan-4-one
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: AQGFSUJMNPZECN-GUFLRTEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  环戊二烯 、 (1S,2R,6S,7R,exo)-N-crotonoyl-3-oxa-5-aza-7-ethyl-10,10-dimethyltricyclo<5.2.1.0^2,6>decan-4-one 在 氯化二乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以91%的产率得到(1S,2R,6S,7R,exo)-N-((3'R,4'S,5'S,6'R)-5'-methylbicyclo<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：

  (+)-7,7-dimethyl-1-vinyl-2-norbornanone 在 palladium on activated charcoal titanium(IV) isopropylate 、 sodium hydroxide 、 乙二醇二甲醚 、 selenium(IV) oxide 、 氢气 、 diethylzinc 、 L-Selectride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸酐 为溶剂， 反应 165.5h， 生成 (1S,2R,6S,7R,exo)-N-crotonoyl-3-oxa-5-aza-7-ethyl-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

文献信息

• Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries
  作者：Malcolm R. Banks、Alexander J. Blake、J.I.G. Cadogan、Allan A. Doyle、Ian Gosney、Philip K.G. Hodgson、Paul Thorburn

  DOI：10.1016/s0040-4020(96)00070-1

  日期：1996.3

  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..