(3S,4R)-4-isopropenyl-1-(menthol-8-yl)-3-(4-methoxyphenyl)pyrrolidin-3-ol | 1200450-69-6

• 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: (3S,4R)-4-isopropenyl-1-(menthol-8-yl)-3-(4-methoxyphenyl)pyrrolidin-3-ol
• 英文别名: (3S,4R)-1-[2-[(1S,2R,4R)-2-hydroxy-4-methylcyclohexyl]propan-2-yl]-3-(4-methoxyphenyl)-4-prop-1-en-2-ylpyrrolidin-3-ol
• CAS: 1200450-69-6
• 化学式: C₂₄H₃₇NO₃
• 分子量: 387.563
• InChiKey: MQWPJRYYORDSDY-JZWLZXDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-isopropenyl-1-(menthol-8-yl)-3-(4-methoxyphenyl)pyrrolidin-3-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成
  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：

  (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