(R_S,1R)-(-)-N-(2-chloro-1,2-diethylbutyl)-tert-butanesulfinamide | 905730-40-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (R_S,1R)-(-)-N-(2-chloro-1,2-diethylbutyl)-tert-butanesulfinamide
• CAS: 905730-40-7
• 化学式: C₁₂H₂₆ClNOS
• 分子量: 267.864
• InChiKey: WXDBIGJZMHDGOB-QLJPJBMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R_S,1R)-(-)-N-(2-chloro-1,2-diethylbutyl)-tert-butanesulfinamide 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (R_S,3R)-(-)-N-(tert-butylsulfinyl)-2,2,3-triethylaziridine
  参考文献：
  名称：

  Use of α-Chlorinated N-(tert-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines

  摘要：

  [GRAPHICS]Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded, beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with base. The diastereoselectivity obtained in the newly synthesized, beta-chloro sulfinamides is explained via the coordinating ability of the alpha-chloro atom with magnesium resulting in the opposite stereochemical outcome as generally observed for nonfunctionalized N-sulfinyl imines.

  DOI：

  10.1021/ol0611245
• 作为产物：
  描述：

  2-氯-2-乙基丁醛 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (R_S,1R)-(-)-N-(2-chloro-1,2-diethylbutyl)-tert-butanesulfinamide
  参考文献：
  名称：

  Use of α-Chlorinated N-(tert-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines

  摘要：

  [GRAPHICS]Reaction of chiral alpha-chloro tert-butanesulfinyl aldimines with Grignard reagents efficiently afforded, beta-chloro N-sulfinamides in high diastereomeric excess. The latter compounds were cyclized toward the corresponding chiral aziridines in a high-yielding one-pot reaction or after separate treatment with base. The diastereoselectivity obtained in the newly synthesized, beta-chloro sulfinamides is explained via the coordinating ability of the alpha-chloro atom with magnesium resulting in the opposite stereochemical outcome as generally observed for nonfunctionalized N-sulfinyl imines.

  DOI：

  10.1021/ol0611245