(1S,2R,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(4-methoxyphenyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol | 1200450-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,2R,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(4-methoxyphenyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol
• CAS: 1200450-51-6
• 化学式: C₂₄H₃₅NO₃
• 分子量: 385.547
• InChiKey: XZINMHVJDCFXPQ-NBBAOLBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(4-methoxyphenyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 以86%的产率得到(3S,4R)-4-isopropenyl-1-(menthol-8-yl)-3-(4-methoxyphenyl)pyrrolidin-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] (4-methoxyphenyl) ketone 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (1R,2S,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(4-methoxyphenyl)-decahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol 、 (1S,2R,4aS,7R,8aR,9aS)-2-isopropenyl-4,4,7-trimethyl-1-(4-methoxyphenyl)-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