(R_S,3R)-(-)-N-(tert-butylsulfinyl)-3-phenyl-2,2-diethylaziridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R_S,3R)-(-)-N-(tert-butylsulfinyl)-3-phenyl-2,2-diethylaziridine
• 英文别名: (3R)-1-[(R)-tert-butylsulfinyl]-2,2-diethyl-3-phenylaziridine
• 化学式: C₁₆H₂₅NOS
• 分子量: 279.447
• InChiKey: JHBWGWUSEYJYRJ-LJMFKLJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  39.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 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 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R_S,3R)-(-)-N-(tert-butylsulfinyl)-3-phenyl-2,2-diethylaziridine
  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.