3β-methoxy-4β-phenyl-2-azetidinone | 155321-73-6

• 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: 3β-methoxy-4β-phenyl-2-azetidinone
• 英文别名: (3S,4R)-3-methoxy-4-phenylazetidin-2-one
• CAS: 155321-73-6
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: XTGLDRZJZOCKAG-BDAKNGLRSA-N

物化性质

• 沸点：
  369.6±42.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 3β-methoxy-4β-phenyl-2-azetidinone 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以53%的产率得到1-acetyl-3β-methoxy-4β-phenyl-2-azetidinone
  参考文献：
  名称：

  d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1

  摘要：

  The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C-3, C-4, and C-1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00264-8
• 作为产物：
  描述：

  在 正丁基锂 、 TEA 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 3β-methoxy-4β-phenyl-2-azetidinone
  参考文献：
  名称：

  d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1

  摘要：

  The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C-3, C-4, and C-1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00264-8

文献信息

• d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1
  作者：Josefa Anaya、Stephane D Gero、Manuel Grande、José Ignacio M Hernando、Nieves M Laso

  DOI：10.1016/s0968-0896(98)00264-8

  日期：1999.5

  The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C-3, C-4, and C-1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. (C) 1999 Elsevier Science Ltd. All rights reserved.