(Rs,S)-N-((E)-1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-yl)-tert-butanesulfinamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Rs,S)-N-((E)-1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-yl)-tert-butanesulfinamide
• 英文别名: (Rs,S)-(-)-N-(3-furyl-1-trifluoromethyl-allyl)-2-methylpropanesulfinamide；(R)-2-methyl-N-[(E,2S)-1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-yl]propane-2-sulfinamide
• 化学式: C₁₂H₁₆F₃NO₂S
• 分子量: 295.326
• InChiKey: WDNAWMDOALYFSF-KCEQNVMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 在 titanium(IV) tetraethanolate 、 四丁基二氟三苯硅酸铵 作用下， 以 四氢呋喃 为溶剂， 生成 (Rs,S)-N-((E)-1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-yl)-tert-butanesulfinamide
  参考文献：
  名称：

  Asymmetric Synthesis of Trifluoromethylated Allylic Amines Using α,β-Unsaturated N-tert-Butanesulfinimines

  摘要：

  [GRAPHICS]The trifluoromethide ion generated in situ from TMSCF3 and TBAT (tetrabutylammonium triphenyldifluorosilicate), as well as TMAF (tetramethylammonium fluoride), adds to the alpha,beta -unsaturated hkert-butanesulfinimines exclusively in a 1,2 fashion with high diastereoselectivities, affording the first examples of chiral trifluoromethylated allylic amines.

  DOI：

  10.1021/ol010134x

文献信息

• Asymmetric synthesis of either diastereomer of trifluoromethylated allylic amines by the selective reduction of trifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines
  作者：Zhen-Jiang Liu、Jin-Tao Liu

  DOI：10.1039/b810459j

  日期：——

  Regio- and diastereoselective reduction of chiraltrifluoromethyl α,β-unsaturated N-tert-butanesulfinyl ketoimines 1 was achieved by choosing appropriate reducing agent and either diastereomer of the corresponding trifluoromethylated allylic amines was obtained with good yield and excellent diastereoselectivity (up to >99 : 1 dr).

  通过选择适当的还原剂，实现了手性三氟甲基δ,δ-不饱和 N-叔丁基亚磺酰酮亚胺 1 的区域和非对映选择性还原，并获得了相应的三氟甲基烯丙基胺的非对映异构体，且收率高，非对映选择性极佳（达 >99 : 1 dr）。
• Asymmetric Synthesis of Trifluoromethylated Allylic Amines Using α,<i>β</i>-Unsaturated <i>N</i>-<i>tert</i>-Butanesulfinimines
  作者：G. K. Surya Prakash、Mihirbaran Mandal、George A. Olah

  DOI：10.1021/ol010134x

  日期：2001.9.1

  [GRAPHICS]The trifluoromethide ion generated in situ from TMSCF3 and TBAT (tetrabutylammonium triphenyldifluorosilicate), as well as TMAF (tetramethylammonium fluoride), adds to the alpha,beta -unsaturated hkert-butanesulfinimines exclusively in a 1,2 fashion with high diastereoselectivities, affording the first examples of chiral trifluoromethylated allylic amines.