(R)-N-[(1S)-1-naphthalen-1-ylbut-3-enyl]-2-phenylpropane-2-sulfinamide | 1428366-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-[(1S)-1-naphthalen-1-ylbut-3-enyl]-2-phenylpropane-2-sulfinamide
• CAS: 1428366-36-2
• 化学式: C₂₃H₂₅NOS
• 分子量: 363.524
• InChiKey: PHWBWPJAFKHQFN-BKMJKUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R_S)-2-phenylpropyl-2-sulfinamide 在 titanium(IV) tetraethanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (R)-N-[(1S)-1-naphthalen-1-ylbut-3-enyl]-2-phenylpropane-2-sulfinamide
  参考文献：
  名称：

  Design, Synthesis, and Applications of Chiral N-2-Phenyl-2-propyl Sulfinyl Imines for Group-Assisted Purification (GAP) Asymmetric Synthesis

  摘要：

  A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (R(s))-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.

  DOI：

  10.1021/jo400354r

文献信息

• Design, Synthesis, and Applications of Chiral <i>N</i>-2-Phenyl-2-propyl Sulfinyl Imines for Group-Assisted Purification (GAP) Asymmetric Synthesis
  作者：Suresh Pindi、Jianbin Wu、Guigen Li

  DOI：10.1021/jo400354r

  日期：2013.4.19

  A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (R(s))-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.