tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate | 505085-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate
• 英文别名: tert-butyl N-[(2S,3R)-1,3-dihydroxy-5-[(R)-(4-methylphenyl)sulfinyl]hex-5-en-2-yl]carbamate
• CAS: 505085-60-9
• 化学式: C₁₈H₂₇NO₅S
• 分子量: 369.482
• InChiKey: WDEAEDDXBQNVJZ-JAUXOLPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.0h， 生成 tert-butyl (4aS,7RS,8aR,R_S)-2,2-dimethyl-7-[(4-methylphenyl)sulfinyl]hexahydro-5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate
  参考文献：
  名称：

  Diastereoselective Route to Piperidine and Indolizidine Scaffolds From Enantiopure Vinylsulfinyl-Containing Amino Alcohols

  摘要：

  A new route to functionalized piperidine and indolizidine scaffolds, based on the diastereoselective intramolecular Michael cyclization of vinyl-sulfinyl-containing amino alcohols 1-3, has been developed. Pyrolytic elimination of the resulting cycloadducts resulted in the regioselective formation of the corresponding tetrahydropyridines and indolizidines. The observed regiochemical course of this process can be explained mainly in terms of the steric bias imposed by the disposition of the arylsulfinyl group and the concerted syn mechanism accepted for this kind of elimination.

  DOI：

  10.1002/1099-0690(200301)2003:1<217::aid-ejoc217>3.0.co;2-w
• 作为产物：
  描述：

  (S)-4-[(R)-1-Hydroxy-3-((R)-toluene-4-sulfinyl)-but-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到tert-butyl (1'S,2'R,R_S)-2-hydroxy-1-(hydroxymethyl)-4-[(4-methylphenyl)sulfinyl]pent-4-enylcarbamate
  参考文献：
  名称：

  Diastereoselective Route to Piperidine and Indolizidine Scaffolds From Enantiopure Vinylsulfinyl-Containing Amino Alcohols

  摘要：

  A new route to functionalized piperidine and indolizidine scaffolds, based on the diastereoselective intramolecular Michael cyclization of vinyl-sulfinyl-containing amino alcohols 1-3, has been developed. Pyrolytic elimination of the resulting cycloadducts resulted in the regioselective formation of the corresponding tetrahydropyridines and indolizidines. The observed regiochemical course of this process can be explained mainly in terms of the steric bias imposed by the disposition of the arylsulfinyl group and the concerted syn mechanism accepted for this kind of elimination.

  DOI：

  10.1002/1099-0690(200301)2003:1<217::aid-ejoc217>3.0.co;2-w

文献信息

• Diastereoselective Route to Piperidine and Indolizidine Scaffolds From Enantiopure Vinylsulfinyl-Containing Amino Alcohols
  作者：Raúl Montoro、Francesc Márquez、Amadeu Llebaria、Antonio Delgado

  DOI：10.1002/1099-0690(200301)2003:1<217::aid-ejoc217>3.0.co;2-w

  日期：2003.1

  A new route to functionalized piperidine and indolizidine scaffolds, based on the diastereoselective intramolecular Michael cyclization of vinyl-sulfinyl-containing amino alcohols 1-3, has been developed. Pyrolytic elimination of the resulting cycloadducts resulted in the regioselective formation of the corresponding tetrahydropyridines and indolizidines. The observed regiochemical course of this process can be explained mainly in terms of the steric bias imposed by the disposition of the arylsulfinyl group and the concerted syn mechanism accepted for this kind of elimination.