(R)-3,3-diphenyl-4-(4-methoxyphenyl)-1-tosylazetidin-2-one | 1231260-44-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-3,3-diphenyl-4-(4-methoxyphenyl)-1-tosylazetidin-2-one
• 英文别名: (4R)-4-(4-methoxyphenyl)-1-(4-methylphenyl)sulfonyl-3,3-diphenylazetidin-2-one
• CAS: 1231260-44-8
• 化学式: C₂₉H₂₅NO₄S
• 分子量: 483.588
• InChiKey: ALCPPJCQZLDAOI-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-甲氧基亚苄基)-4-甲基苯磺酰胺 、 二苯乙烯酮 在 (3aR,7aR)-1,3-bis(naphthalen-1-ylmethyl)-3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazol-3-ium tetrafluoroborate 、 双(三甲基硅烷基)氨基钾 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 生成 (S)-3,3-diphenyl-4-(4-methoxyphenyl)-1-tosylazetidin-2-one 、 (R)-3,3-diphenyl-4-(4-methoxyphenyl)-1-tosylazetidin-2-one
  参考文献：
  名称：

  Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2010.03.001

文献信息

• 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.