(1R,2S,4R,6R,9S,13R)-6,10,10-trimethyl-19-nitro-3-oxa-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-15(20),16,18-trien-12-one | 402858-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S,4R,6R,9S,13R)-6,10,10-trimethyl-19-nitro-3-oxa-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-15(20),16,18-trien-12-one
• CAS: 402858-41-7
• 化学式: C₂₂H₂₈N₂O₄
• 分子量: 384.475
• InChiKey: DZYZZOGXBWOLBG-GRVGLTRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 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：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R,6R,9S,13R)-6,10,10-trimethyl-19-nitro-3-oxa-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-15(20),16,18-trien-12-one 在 aluminium hydride 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.13h， 生成 (3aR,9aR)-5-nitro-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：

  2-nitrocinnamaldehyde 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.5h， 生成 (1R,2S,4R,6R,9S,13R)-6,10,10-trimethyl-19-nitro-3-oxa-11-azapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-15(20),16,18-trien-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

文献信息

• Stereocontrolled IMDA Reaction of Styrene Derivatives. A Way to Enantiopure 3a,4,9,9a-Tetrahydrobenz[<i>f</i>]isoindolines
  作者：Rafael Pedrosa、Celia Andrés、Javier Nieto

  DOI：10.1021/jo010746v

  日期：2002.2.1

  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.