(3R,4S)-1-(menthol-8-yl)-3-phenyl-4-(1-phenylvinyl)pyrrolidin-3-ol | 1200450-65-2

• 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: (3R,4S)-1-(menthol-8-yl)-3-phenyl-4-(1-phenylvinyl)pyrrolidin-3-ol
• CAS: 1200450-65-2
• 化学式: C₂₈H₃₇NO₂
• 分子量: 419.607
• InChiKey: SENABAAOODNIAA-SDYMTIEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.7
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-(menthol-8-yl)-3-phenyl-4-(1-phenylvinyl)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：

  (1R,2S,4aS,7R,8aR,9aS)-1-phenyl-2-(1-phenylvinyl)-4,4,7-trimethyldecahydro-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90%的产率得到(3R,4S)-1-(menthol-8-yl)-3-phenyl-4-(1-phenylvinyl)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