8-amino-N-phenylselenoethyl-N-prenylmenthol | 323999-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 8-amino-N-phenylselenoethyl-N-prenylmenthol
• 英文别名: (1R,2S,5R)-5-methyl-2-[2-[3-methylbut-2-enyl(2-phenylselanylethyl)amino]propan-2-yl]cyclohexan-1-ol
• CAS: 323999-92-4
• 化学式: C₂₃H₃₇NOSe
• 分子量: 422.513
• InChiKey: MHHYDMPKVXVMSA-CEMLEFRQSA-N

物化性质

• 沸点：
  492.3±41.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-amino-N-phenylselenoethyl-N-prenylmenthol 在 氢氧化钾 、 molecular sieve 、 偶氮二异丁腈 、 水 、 三正丁基氢锡 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 长叶薄荷酮
  参考文献：
  名称：

  A Novel Case of Diastereoselection in 5-exo Radical Cyclization Promoted by Hydrogen Bonding

  摘要：

  Moderate stereocontrol in 5-exo radical cyclizations of N,N-disubstituted (-)-8-amino menthol derivatives, promoted by tributyltin hydride and AIBN, was achieved. The stereoselection was explained in terms of hydrogen bond formation in the 1,3-amino alcohol derivative. The presence of one additional stereocenter at the allylic chain enhanced the stereoselection giving a single cyclization stereoisomer. The cyclization products were easily converted into enantiopure 5-alkyl- or 2,3-dialkyl-substituted pyrrolidines.

  DOI：

  10.1002/1099-0690(200011)2000:22<3727::aid-ejoc3727>3.0.co;2-c
• 作为产物：
  描述：

  N-(phenylseleno)ethyl-2α-(2',2'-dimethylvinyl)-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazine 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以70%的产率得到8-amino-N-phenylselenoethyl-N-prenylmenthol
  参考文献：
  名称：

  A Novel Case of Diastereoselection in 5-exo Radical Cyclization Promoted by Hydrogen Bonding

  摘要：

  Moderate stereocontrol in 5-exo radical cyclizations of N,N-disubstituted (-)-8-amino menthol derivatives, promoted by tributyltin hydride and AIBN, was achieved. The stereoselection was explained in terms of hydrogen bond formation in the 1,3-amino alcohol derivative. The presence of one additional stereocenter at the allylic chain enhanced the stereoselection giving a single cyclization stereoisomer. The cyclization products were easily converted into enantiopure 5-alkyl- or 2,3-dialkyl-substituted pyrrolidines.

  DOI：

  10.1002/1099-0690(200011)2000:22<3727::aid-ejoc3727>3.0.co;2-c