(2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[(E)-2-phenylprop-1-enyl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine | 402858-28-0

• 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: (2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[(E)-2-phenylprop-1-enyl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine
• CAS: 402858-28-0
• 化学式: C₂₀H₂₉NO
• 分子量: 299.456
• InChiKey: UXMPKZFNVYZNMZ-NTPGTIBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[(E)-2-phenylprop-1-enyl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine 在 aluminium hydride 、 氢氧化钾 、 3 A molecular sieve 、 potassium carbonate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 3.17h， 生成 (3S,4S)-3-methyl-4-(1-phenylethenyl)pyrrolidine
  参考文献：
  名称：

  非手性分子内Alder-Ene对手性过氢-1,3-苯并恶嗪的反应。快速进入对映纯的顺式-3,4-二取代的吡咯烷类化合物

  摘要：

  衍生自（-）-8-氨基薄荷醇的手性3-丙烯酰基-2-乙烯基取代的1,3-全氢苯并恶嗪参与烯键反应，生成具有优异非对映选择性的3,4-二取代吡咯烷酮衍生物。消除手性佐剂后，将环加合物转化为对映体纯的3,4-二取代的吡咯烷。

  DOI：

  10.1021/jo050360a
• 作为产物：
  描述：

  (E)-3-phenylbut-2-en-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.33h， 生成 (2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[(E)-2-phenylprop-1-enyl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine
  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.
• Diastereoselective Intramolecular Alder−Ene Reaction on Chiral Perhydro-1,3-benzoxazines. A Rapid Entry to Enantiopure <i>cis</i>-3,4-Disubstituted Pyrrolidines
  作者：Rafael Pedrosa、Celia Andrés、Laura Martín、Javier Nieto、Carlos Rosón

  DOI：10.1021/jo050360a

  日期：2005.5.1

  Chiral 3-acryloyl-2-vinyl-substituted 1,3-perhydrobenzoxazines derived from (−)-8-aminomenthol participate in an ene reaction leading to 3,4-disubstituted pyrrolidinone derivates with excellent diastereoselectivity. The cycloadducts were transformed into enantiopure 3,4-disubstituted pyrrolidines after elimination of the chiral adjuvant.

  衍生自（-）-8-氨基薄荷醇的手性3-丙烯酰基-2-乙烯基取代的1,3-全氢苯并恶嗪参与烯键反应，生成具有优异非对映选择性的3,4-二取代吡咯烷酮衍生物。消除手性佐剂后，将环加合物转化为对映体纯的3,4-二取代的吡咯烷。