3-isocyanatopropiophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-isocyanatopropiophenone
• 英文别名: 3-Isocyanato-1-phenylpropan-1-one
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: VHXUJFSUGMMXOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-isocyanatopropiophenone 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以4.41 g的产率得到N-甲基-3-苯基-3-羟基丙胺
  参考文献：
  名称：

  氟西汀的新合成路线

  摘要：

  外消旋氟西汀由 3-苯甲酰丙酸分五步合成，总产率为 54%。

  DOI：

  10.1080/00397910903422518
• 作为产物：
  描述：

  3-苯丙烯溴酸酯 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 3-isocyanatopropiophenone
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003

文献信息

• Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones
  作者：Shrenik K. Shah、Conrad P. Dorn、Paul E. Finke、Jeffrey J. Hale、William K. Hagmann、Karen A. Brause、Gilbert O. Chandler、Amy L. Kissinger、Bonnie M. Ashe

  DOI：10.1021/jm00099a003

  日期：1992.10

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.
• Novel Synthetic Route to Fluoxetine
  作者：Matthias Schulze

  DOI：10.1080/00397910903422518

  日期：2010.10.20

  Racemic fluoxetine was synthesized from 3-benzoylpropionic acid in five steps in 54% overall yield.

  外消旋氟西汀由 3-苯甲酰丙酸分五步合成，总产率为 54%。