(3R,4aR,5aR,5bS,11aS,13aS)-3,13,13-Trimethyl-2,3,4,4a,5b,6,11,11a,13,13a-decahydro-1H,5aH-5-oxa-12a-aza-dibenzo[b,h]fluoren-12-one | 402858-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (3R,4aR,5aR,5bS,11aS,13aS)-3,13,13-Trimethyl-2,3,4,4a,5b,6,11,11a,13,13a-decahydro-1H,5aH-5-oxa-12a-aza-dibenzo[b,h]fluoren-12-one
• 英文别名: (1S,2R,4R,6R,9S,13S)-6,10,10-trimethyl-3-oxa-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-15,17,19-trien-12-one
• CAS: 402858-45-1
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: HMKNZIYYTSYVFV-HTBSWXFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4aR,5aR,5bS,11aS,13aS)-3,13,13-Trimethyl-2,3,4,4a,5b,6,11,11a,13,13a-decahydro-1H,5aH-5-oxa-12a-aza-dibenzo[b,h]fluoren-12-one 在 aluminium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.13h， 以87%的产率得到(3aS,9aS)-N-(8-mentholyl)-3a,4,9,9a-tetrahydrobenz[f]isoindoline
  参考文献：
  名称：

  Stereocontrolled IMDA Reaction of Styrene Derivatives. A Way to Enantiopure 3a,4,9,9a-Tetrahydrobenz[f]isoindolines

  摘要：

  IMDA reactions on chiral perhydro-1,3-benzoxazines, derived from (-)-8-amino menthol, bearing a styrene substituent at C-2 acting as diene and an acryl amide acting as dienophile occur with high stereoselection and excellent chemical yields. After elimination of the chiral appendage, enantiopure 3a,4,9,9a-tetrahydrobenz[f]isoindolines are prepared in this way. The effect of the substituents at both diene and dienophile are studied, showing that a methyl group at C-1 in the diene inhibited the reaction, while the ene adduct, instead of the IMDA product, was obtained when a methyl group was at C-2.

  DOI：

  10.1021/jo010746v
• 作为产物：
  描述：

  (2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-((E)-styryl)-octahydro-benzo[e][1,3]oxazine 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 3.83h， 生成 (3R,4aR,5aR,5bS,11aS,13aS)-3,13,13-Trimethyl-2,3,4,4a,5b,6,11,11a,13,13a-decahydro-1H,5aH-5-oxa-12a-aza-dibenzo[b,h]fluoren-12-one
  参考文献：
  名称：

  Stereocontrolled IMDA Reaction of Styrene Derivatives. A Way to Enantiopure 3a,4,9,9a-Tetrahydrobenz[f]isoindolines

  摘要：

  IMDA reactions on chiral perhydro-1,3-benzoxazines, derived from (-)-8-amino menthol, bearing a styrene substituent at C-2 acting as diene and an acryl amide acting as dienophile occur with high stereoselection and excellent chemical yields. After elimination of the chiral appendage, enantiopure 3a,4,9,9a-tetrahydrobenz[f]isoindolines are prepared in this way. The effect of the substituents at both diene and dienophile are studied, showing that a methyl group at C-1 in the diene inhibited the reaction, while the ene adduct, instead of the IMDA product, was obtained when a methyl group was at C-2.

  DOI：

  10.1021/jo010746v