N-(p-fluorobenzylidene)trifluoromethanesulfonamide | 110524-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(p-fluorobenzylidene)trifluoromethanesulfonamide
• 英文别名: 1,1,1-trifluoro-N-[(4-fluorophenyl)methylene]methanesulfonamide；(NE)-1,1,1-trifluoro-N-[(4-fluorophenyl)methylidene]methanesulfonamide
• CAS: 110524-94-2
• 化学式: C₈H₅F₄NO₂S
• 分子量: 255.193
• InChiKey: FGSVWEPVTBLPRD-WLRTZDKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(p-fluorobenzylidene)trifluoromethanesulfonamide 在 氢氧化钾 、 lithium aluminium tetrahydride 、 (Me₅-cyclopentadienyl)(4-N-pyrrolidinyl-pyridinyl)Fe⁽²⁺⁾ 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 Trifluoro-acetic acid (2R,3R)-3-(4-fluoro-phenyl)-2-methyl-2-phenyl-3-trifluoromethanesulfonylamino-propyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Staudinger Reactions to Form β-Lactams:  An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent

  摘要：

  There are relatively few methods for the catalytic asymmetric synthesis of beta-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans beta-lactams (trans = relationship of Ph to R1). The key to this method is the use of an N-triflyl protecting group for the imine. Along with serving as interesting targets in their own right, N-triflyl beta-lactams readily react with nucleophiles to generate useful families of compounds, such as gamma-amino alcohols and beta-amino acids.

  DOI：

  10.1021/ja052058p
• 作为产物：
  描述：

  N-sulfinyltrifluoromethanesulfonamide 、 对氟苯甲醛 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以75%的产率得到N-(p-fluorobenzylidene)trifluoromethanesulfonamide
  参考文献：
  名称：

  Catalytic Asymmetric Staudinger Reactions to Form β-Lactams:  An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent

  摘要：

  There are relatively few methods for the catalytic asymmetric synthesis of beta-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans beta-lactams (trans = relationship of Ph to R1). The key to this method is the use of an N-triflyl protecting group for the imine. Along with serving as interesting targets in their own right, N-triflyl beta-lactams readily react with nucleophiles to generate useful families of compounds, such as gamma-amino alcohols and beta-amino acids.

  DOI：

  10.1021/ja052058p

文献信息

• Yagupol'skii, L. M.; Popov, V. I.; Pavlenko, N. V., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 10, p. 1947 - 1950
  作者：Yagupol'skii, L. M.、Popov, V. I.、Pavlenko, N. V.、Maletina, I. I.、Mironova, A. A.、et al.

  DOI：——

  日期：——
• YAGUPOLSKIJ L. M.; POPOV V. I.; PAVLENKO N. V.; MALETINA I. I.; MIRONOVA +, ZH. ORGAN. XIMII, 22,(1986) N 10, 2169-2173
  作者：YAGUPOLSKIJ L. M.、 POPOV V. I.、 PAVLENKO N. V.、 MALETINA I. I.、 MIRONOVA +

  DOI：——

  日期：——
• Catalytic Asymmetric Staudinger Reactions to Form β-Lactams:  An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent
  作者：Elaine C. Lee、Brian L. Hodous、Enda Bergin、Crystal Shih、Gregory C. Fu

  DOI：10.1021/ja052058p

  日期：2005.8.24

  There are relatively few methods for the catalytic asymmetric synthesis of beta-lactams, and those that have been reported are generally cis selective. This communication describes the first catalytic enantioselective Staudinger reactions that preferentially furnish trans beta-lactams (trans = relationship of Ph to R1). The key to this method is the use of an N-triflyl protecting group for the imine. Along with serving as interesting targets in their own right, N-triflyl beta-lactams readily react with nucleophiles to generate useful families of compounds, such as gamma-amino alcohols and beta-amino acids.