8-amino-O-tert-butyldimethylsilyl-N-phenylselenoethyl-N-prenylmenthol | 323999-94-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 8-amino-O-tert-butyldimethylsilyl-N-phenylselenoethyl-N-prenylmenthol
• 英文别名: N-[2-[(1S,2R,4R)-2-[tert-butyl(dimethyl)silyl]oxy-4-methylcyclohexyl]propan-2-yl]-3-methyl-N-(2-phenylselanylethyl)but-2-en-1-amine
• CAS: 323999-94-6
• 化学式: C₂₉H₅₁NOSeSi
• 分子量: 536.776
• InChiKey: AHWUEENBPDAPEY-ZRJLEYOISA-N

物化性质

• 沸点：
  527.5±46.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-amino-O-tert-butyldimethylsilyl-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 咪唑 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.25h， 生成 8-amino-O-tert-butyldimethylsilyl-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

文献信息

• A Novel Case of Diastereoselection in 5-exo Radical Cyclization Promoted by Hydrogen Bonding
  作者：Rafael Pedrosa、Celia Andrés、Juan P. Duque-Soladana、Pilar Mendiguchía

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

  日期：2000.11

  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.