(R_S)-(-)-N-((1-chlorocyclohexyl)methylidene)-tert-butanesulfinamide | 905730-20-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: (R_S)-(-)-N-((1-chlorocyclohexyl)methylidene)-tert-butanesulfinamide
• 英文别名: (NE,R)-N-[(1-chlorocyclohexyl)methylidene]-2-methylpropane-2-sulfinamide
• CAS: 905730-20-3
• 化学式: C₁₁H₂₀ClNOS
• 分子量: 249.805
• InChiKey: MTJYODCIJPECIS-BMQCOBNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R_S)-(-)-N-((1-chlorocyclohexyl)methylidene)-tert-butanesulfinamide 、 苯基氯化镁 在 氢氧化钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以20%的产率得到(R_S,2R)-(-)-N-(tert-butylsulfinyl)-2-phenyl-1-azaspiro[2.5]octane
  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：

  1-氯环己烷-1-甲醛 、 (R)-(+)-叔丁基亚磺酰胺 在 titanium(IV) tetraethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%的产率得到(R_S)-(-)-N-((1-chlorocyclohexyl)methylidene)-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

文献信息

• Use of <i>α</i><i>-</i>Chlorinated <i>N-</i>(<i>tert</i>-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines
  作者：Bram Denolf、Sven Mangelinckx、Karl W. Törnroos、Norbert De Kimpe

  DOI：10.1021/ol0611245

  日期：2006.7.1

  [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.