(2S,4aS,7R,8aR)-[3-(3-methylbut-2-enyl)-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl] p-tolyl ketone | 1200450-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4aS,7R,8aR)-[3-(3-methylbut-2-enyl)-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl] p-tolyl ketone
• 英文别名: [(2S,4aS,7R,8aR)-4,4,7-trimethyl-3-(3-methylbut-2-enyl)-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-2-yl]-(4-methylphenyl)methanone
• CAS: 1200450-42-5
• 化学式: C₂₄H₃₅NO₂
• 分子量: 369.547
• InChiKey: HRCHSJYXZFIMCZ-LPOZWGFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4aS,7R,8aR)-[3-(3-methylbut-2-enyl)-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl] p-tolyl ketone 在 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (1R,2S,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(p-tolyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol 、 (1S,2R,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(p-tolyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol
  参考文献：
  名称：

  Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines

  摘要：

  Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 degrees C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.091
• 作为产物：
  描述：

  4-甲基苯甲酰甲醛水合物 、 (-)-aminomenthol 、 1-溴-3-甲基-2-丁烯 在 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 以82%的产率得到(2S,4aS,7R,8aR)-[3-(3-methylbut-2-enyl)-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl] p-tolyl ketone
  参考文献：
  名称：

  Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines

  摘要：

  Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 degrees C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.091

文献信息

• Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines
  作者：Celia Andrés、Israel González、Javier Nieto、Carlos D. Rosón

  DOI：10.1016/j.tet.2009.09.091

  日期：2009.11

  Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 degrees C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. (C) 2009 Elsevier Ltd. All rights reserved.