(+)-3-(4-fluorophenyl)-1,2-thiazolidine 1,1-dioxide | 1166859-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (+)-3-(4-fluorophenyl)-1,2-thiazolidine 1,1-dioxide
• 英文别名: (3R)-3-(4-fluorophenyl)-1,2-thiazolidine 1,1-dioxide
• CAS: 1166859-61-5
• 化学式: C₉H₁₀FNO₂S
• 分子量: 215.248
• InChiKey: RVBFESBUYYAXNL-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (±)-4-氟苯乙烯环氧化物 在 palladium(II) trifluoroacetate 、 (S,S)-f-binaphane 、 D(+)-10-樟脑磺酸 、 氢气 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， -78.0~50.0 ℃ 、4.14 MPa 条件下， 反应 24.0h， 生成 (+)-3-(4-fluorophenyl)-1,2-thiazolidine 1,1-dioxide
  参考文献：
  名称：

  Synthesis of chiral γ -sultams through intramolecular reductive amination with sulfonylcarbamate as N- source

  摘要：

  An efficient and enantioselective palladium-catalyzed intramolecular asymmetric reductive amination with sulfonylcarbamates as N-sources was reported, providing a facile and general access to the chiral gamma-sultam derivatives with up to 97% of enantioselectivity. This tandem process avoids additional deprotection manipulation and arduous isolation of the N-sulfonyl-imine intermediates. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.03.012

文献信息

• Highly Enantioselective Synthesis of Sultams via Pd-Catalyzed Hydrogenation
  作者：Chang-Bin Yu、Da-Wei Wang、Yong-Gui Zhou

  DOI：10.1021/jo900790k

  日期：2009.8.7

  Using pd(cf3co2)2/(S,S)-f-Binaphane as the catalyst, an efficient enantioselective synthesis of sultams was developed via asymmetric hydrogenation of the corresponding cyclic imines with high enantioselectivities. The hydrogenation products can be conveniently transformed to chiral homoallylic amines without loss of enantioselectivity.

  以pd（cf 3 co 2）2 /（S，S）-f-Binaphane为催化剂，通过高对映选择性的相应环状亚胺的不对称加氢反应，开发了有效的对映异构体。氢化产物可以方便地转化为手性均烯丙基胺，而不会损失对映选择性。
• Synthesis of chiral γ -sultams through intramolecular reductive amination with sulfonylcarbamate as N- source
  作者：Bo Song、Yue Ji、Shu-Bo Hu、Chang-Bin Yu、Yong-Gui Zhou

  DOI：10.1016/j.tetlet.2017.03.012

  日期：2017.4

  An efficient and enantioselective palladium-catalyzed intramolecular asymmetric reductive amination with sulfonylcarbamates as N-sources was reported, providing a facile and general access to the chiral gamma-sultam derivatives with up to 97% of enantioselectivity. This tandem process avoids additional deprotection manipulation and arduous isolation of the N-sulfonyl-imine intermediates. (C) 2017 Elsevier Ltd. All rights reserved.