N-acryloyl-2α-cinnamyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine | 220985-08-0

• 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: N-acryloyl-2α-cinnamyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine
• 英文别名: N-acryloyl-2α-(2-trans-phenylethenyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine；1-[(2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[(E)-2-phenylethenyl]-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-3-yl]prop-2-en-1-one
• CAS: 220985-08-0
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: ATZVWPUQNNJROQ-UTPNVUJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-acryloyl-2α-cinnamyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 在 盐酸 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 3.83h， 生成 (3R,4aR,5aR,5bR,11aR,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
• 作为产物：
  描述：

  (-)-aminomenthol 在 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 N-acryloyl-2α-cinnamyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine
  参考文献：
  名称：

  Regio- and diastereoselective tandem addition–carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines

  摘要：

  Radical addition-carbocyclization of 2-allyl-3-acyloyl-substituted perhydro-1,3-benzoxazines readily provides 3,4-disubstituted pyrrolidinone derivatives with total regioselectivity and good diastereoselectivity. The key step of the reaction is a tandem addition-5-exo-cyclization promoted by a sulfanyl radical. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.06.003

文献信息

• Tributyltin radical-induced addition–carbocyclization on chiral perhydro-1,3-benzoxazines: a facile entry to enantiopure tin-containing auxiliaries
  作者：Celia Andrés、Juan Pablo Duque-Soladana、Rafael Pedrosa

  DOI：10.1039/a807773h

  日期：——

  N-Acryloylperhydro-1,3-benzoxazines 1a,b undergo stereo-selective addition–carbocyclization when reacted with Bu3SnH, leading to stannylated lactamic rings that can be transformed into enantiopure pyrrolidines.

  N-丙烯酰基过氢-1,3-苯并噁嗪 1a,b 与 Bu3SnH 反应时发生立体选择性加成-碳环化，生成的锡基乳酸环可以转化为对映体纯的呋喃烷。
• Synthesis of Enantiopure 3-Azabicyclo[3.2.0]heptanes by Diastereoselective Intramolecular [2+2] Photocycloaddition Reactions on Chiral Perhydro-1,3-benzoxazines
  作者：Rafael Pedrosa、Celia Andrés、Javier Nieto、Soledad del Pozo

  DOI：10.1021/jo034251c

  日期：2003.6.1

  [2+2] photocycloadditions involving chiral 3-acryloyl-2-vinylperhydro-1,3-benzoxazines derived from (-)-8-aminomenthol are highly diastereoselective reactions. The facial selectivity depends on the type of substitution at the vinyl double bond, and always leads to cis-fused bicyclic derivatives. The de is good for compounds with one substituent at the outer carbon of the double bond at C-2, but only

  [2 + 2]涉及衍生自（-）-8-氨基薄荷醇的手性3-丙烯酰基-2-乙烯基过氢-1,3-苯并恶嗪的[2 + 2]光环加成反应是高度非对映选择性反应。面部选择性取决于在乙烯基双键处的取代类型，并且总是导致顺式稠合的双环衍生物。de对于在C-2的双键的外部碳原子上具有一个取代基的化合物是有利的，但是在该位置具有两个取代基的化合物的环化中仅形成一个非对映异构体。消除薄荷醇附肢得到对映体纯的3-氮杂双环[3.2.0]庚烷。
• Regio- and diastereoselective tandem addition–carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines
  作者：Rafael Pedrosa、Celia Andrés、Juan P. Duque-Soladana、Alicia Maestro、Javier Nieto

  DOI：10.1016/j.tetasy.2003.06.003

  日期：2003.10

  Radical addition-carbocyclization of 2-allyl-3-acyloyl-substituted perhydro-1,3-benzoxazines readily provides 3,4-disubstituted pyrrolidinone derivatives with total regioselectivity and good diastereoselectivity. The key step of the reaction is a tandem addition-5-exo-cyclization promoted by a sulfanyl radical. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.