(S)-3,3-diphenyl-4-(2-furanyl)-1-tosylazetidin-2-one | 1021955-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (S)-3,3-diphenyl-4-(2-furanyl)-1-tosylazetidin-2-one
• 英文别名: (4S)-4-(furan-2-yl)-1-(4-methylphenyl)sulfonyl-3,3-diphenylazetidin-2-one
• CAS: 1021955-33-8
• 化学式: C₂₆H₂₁NO₄S
• 分子量: 443.523
• InChiKey: PQYIFNZAJDUAIU-XMMPIXPASA-N

物化性质

• 熔点：
  144-146 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  573.0±60.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯乙烯酮 、 2-furaldehyde tosylimine 在 (3aR,7aR)-1,3-dibenzyl-3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazolium tetrafluoroborate 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 生成 (S)-3,3-diphenyl-4-(2-furanyl)-1-tosylazetidin-2-one
  参考文献：
  名称：

  N-Heterocyclic carbene catalysed β-lactam synthesis

  摘要：

  N-杂环卡宾促进了酮烯与N-托烯亚胺的形式[2+2]环加成反应，得到相应的β-内酯，收率在良好到优良范围内；手性NHC在结晶后给予高光学纯度的β-内酯。

  DOI：

  10.1039/b800857b

文献信息

• Chiral relay in NHC-mediated asymmetric β-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines
  作者：Nicolas Duguet、Adele Donaldson、Stuart M. Leckie、Eddy A. Kallström、Craig D. Campbell、Peter Shapland、Thomas B. Brown、Alexandra M.Z. Slawin、Andrew D. Smith

  DOI：10.1016/j.tetasy.2010.03.002

  日期：2010.3

  The synthesis of a range of imidazolinium salts derived from acyclic 1,2-diamines, and an evaluation of the reactivity and asymmetric induction of the corresponding NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. An N-methyl-substituted NHC derived from (1R,2R)-1,2-diphenylethanediamine shows optimal reactivity and enantioselectivity in this series, in contrast to that observed with NHCs derived from (1R,2R)-cyclohexane-1,2-diamine. (C) 2010 Elsevier Ltd. All rights reserved.
• Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine
  作者：Nicolas Duguet、Adele Donaldson、Stuart M. Leckie、James Douglas、Peter Shapland、Thomas B. Brown、Gwydion Churchill、Alexandra M.Z. Slawin、Andrew D. Smith

  DOI：10.1016/j.tetasy.2010.03.001

  日期：2010.3

  The synthesis of a range of C-2-symmetric imidazolinium salts from (1R,2R)-cyclohexane-1,2-diamine, and an evaluation of the reactivity and asymmetric induction of the derived NHCs as catalysts for the asymmetric synthesis of beta-lactams, is reported. In this series, optimal enantioselectivity (up to 70% ee) is observed using N-benzyl or N-1-naphthylmethyl-substituted NHCs, consistent with a chiral relay effect operating to dictate the stereochemical outcome of this reaction. (C) 2010 Elsevier Ltd. All rights reserved.
• N-Heterocyclic carbene catalysed β-lactam synthesis
  作者：Nicolas Duguet、Craig D. Campbell、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1039/b800857b

  日期：——

  N-Heterocyclic carbenes promote the formal [2+2] cycloaddition of ketenes with N-tosyl imines to give the corresponding β-lactams in good to excellent isolated yields; chiral NHCs give β-lactams in high e.e. after crystallisation.

  N-杂环卡宾促进了酮烯与N-托烯亚胺的形式[2+2]环加成反应，得到相应的β-内酯，收率在良好到优良范围内；手性NHC在结晶后给予高光学纯度的β-内酯。