cis-1-tert-butyl-3-methoxy-4-(4-methylphenyl)azetidin-2-one

• 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: cis-1-tert-butyl-3-methoxy-4-(4-methylphenyl)azetidin-2-one
• 英文别名: (3S,4R)-1-tert-butyl-3-methoxy-4-(4-methylphenyl)azetidin-2-one
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: GDCTYZSSHOPFIT-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1-tert-butyl-3-methoxy-4-(4-methylphenyl)azetidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以32%的产率得到syn-3-tert-butylamino-2-methoxy-3-(4-methylphenyl)propan-1-ol
  参考文献：
  名称：

  Synthesis of Novel 2-Alkoxy-3-amino-3-arylpropan-1-ols and 5-Alkoxy-4-aryl-1,3-oxazinanes with Antimalarial Activity

  摘要：

  A variety of novel syn-2-alkoxy-3-amino-3-arylpropan-1-ols was prepared through LiAlH4-promoted reductive ring-opening of cis-3-alkoxy-4-aryl-beta-lactams in Et2O. The latter gamma-aminoalcohols were easily converted into cis-5-alkoxy-4-aryl-1,3-oxazinanes using formaldehyde in THE Both series of compounds were evaluated against a chloroquine sensitive strain of Plasmodium falciparum (D10), revealing micromolar potency for almost all representatives. Eleven compounds exhibited antimalarial activity with IC50 values of <= 30 mu M, and the majority of these compounds did not show cytotoxicity at the concentrations tested.

  DOI：

  10.1021/jm9002632
• 作为产物：
  描述：

  甲氧基乙酰氯 、 p-methylbenzylidene-tert-butylamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到cis-1-tert-butyl-3-methoxy-4-(4-methylphenyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis of Novel 2-Alkoxy-3-amino-3-arylpropan-1-ols and 5-Alkoxy-4-aryl-1,3-oxazinanes with Antimalarial Activity

  摘要：

  A variety of novel syn-2-alkoxy-3-amino-3-arylpropan-1-ols was prepared through LiAlH4-promoted reductive ring-opening of cis-3-alkoxy-4-aryl-beta-lactams in Et2O. The latter gamma-aminoalcohols were easily converted into cis-5-alkoxy-4-aryl-1,3-oxazinanes using formaldehyde in THE Both series of compounds were evaluated against a chloroquine sensitive strain of Plasmodium falciparum (D10), revealing micromolar potency for almost all representatives. Eleven compounds exhibited antimalarial activity with IC50 values of <= 30 mu M, and the majority of these compounds did not show cytotoxicity at the concentrations tested.

  DOI：

  10.1021/jm9002632

文献信息

• Synthesis of Novel 2-Alkoxy-3-amino-3-arylpropan-1-ols and 5-Alkoxy-4-aryl-1,3-oxazinanes with Antimalarial Activity
  作者：Matthias D’hooghe、Stijn Dekeukeleire、Karen Mollet、Carmen Lategan、Peter J. Smith、Kelly Chibale、Norbert De Kimpe

  DOI：10.1021/jm9002632

  日期：2009.7.9

  A variety of novel syn-2-alkoxy-3-amino-3-arylpropan-1-ols was prepared through LiAlH4-promoted reductive ring-opening of cis-3-alkoxy-4-aryl-beta-lactams in Et2O. The latter gamma-aminoalcohols were easily converted into cis-5-alkoxy-4-aryl-1,3-oxazinanes using formaldehyde in THE Both series of compounds were evaluated against a chloroquine sensitive strain of Plasmodium falciparum (D10), revealing micromolar potency for almost all representatives. Eleven compounds exhibited antimalarial activity with IC50 values of <= 30 mu M, and the majority of these compounds did not show cytotoxicity at the concentrations tested.