2α-[2-trans-(2'-nitrophenyl)ethenyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine | 402858-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2α-[2-trans-(2'-nitrophenyl)ethenyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine
• 英文别名: (2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[(E)-2-(2-nitrophenyl)ethenyl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine
• CAS: 402858-26-8
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: UHYSDDOHHKTHSB-SRASXRPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2α-[2-trans-(2'-nitrophenyl)ethenyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 在 aluminium hydride 、 盐酸 、 4 A molecular sieve 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 3.96h， 生成 (3aS,9aS)-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 、 (-)-aminomenthol 以 甲苯 为溶剂， 以94%的产率得到2α-[2-trans-(2'-nitrophenyl)ethenyl]-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine
  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

• Regio- and Stereoselective Methoxyselenenylation of Chiral 2-Vinyl Perhydro-1,3-benzoxazines Promoted by Selenium-Heteroatom Nonbonded Interactions
  作者：Rafael Pedrosa、Celia Andrés、Raquel Arias、Pilar Mendiguchía、Javier Nieto

  DOI：10.1021/jo052582e

  日期：2006.3.1

  Regio- and diastereoselective rnethoxyselenenylations of double bonds attached to the N,O-ketalic carbon of chiral perhydrobenzoxazines occur in high yields by reaction with benzeneselenenyl chloride in dichloromethane-methanol. The diastereoselection is dependent on the reaction conditions and the structure of the starting compounds and can be rationalized by accepting the coordination of the selenium to the oxygen atom of the heterocycle.
• 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.