(1R,2S,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(p-tolyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol | 1200450-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,2S,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(p-tolyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol
• CAS: 1200450-48-1
• 化学式: C₂₄H₃₅NO₂
• 分子量: 369.547
• InChiKey: HLWRLZJTSASMAG-OMGSTURQSA-N

物化性质

• 沸点：
  479.1±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(p-tolyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(3R,4S)-4-isopropenyl-1-(menthol-8-yl)-3-p-tolylpyrrolidin-3-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：

  (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