N-[(1-ethoxycarbonylcycloprop-1-yl)carbonylmethyl]-N-[(S)-1-phenylethyl]-2-(diethoxyphosphoryl)-2-fluoroacetamide | 412295-21-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: N-[(1-ethoxycarbonylcycloprop-1-yl)carbonylmethyl]-N-[(S)-1-phenylethyl]-2-(diethoxyphosphoryl)-2-fluoroacetamide
• 英文别名: ethyl 1-[2-[(2-diethoxyphosphoryl-2-fluoroacetyl)-[(1S)-1-phenylethyl]amino]acetyl]cyclopropane-1-carboxylate
• CAS: 412295-21-7
• 化学式: C₂₂H₃₁FNO₇P
• 分子量: 471.463
• InChiKey: RVLXVFGBPVAOLD-UCFFOFKASA-N

物化性质

• 沸点：
  578.1±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-[(1-ethoxycarbonylcycloprop-1-yl)carbonylmethyl]-N-[(S)-1-phenylethyl]-2-(diethoxyphosphoryl)-2-fluoroacetamide 在 4 Angstroem MS 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以83%的产率得到ethyl 1-{4-fluoro-2,5-dihydro-5-oxo-1-[(S)-1-phenylethyl]-1H-pyrrol-3-yl}cyclopropanecarboxylate
  参考文献：
  名称：

  Practical Synthesis of DQ-113, a New Quinolone Antibacterial Agent, by Using the Intramolecular Horner-Wadsworth- Emmons Reaction

  摘要：

  A practical route was developed for synthesizing the C-7 substituent of DQ-113 (6, 5-amino-7-[(3S,4R)-4-(1-aminocycloprop-l-yl)-3-fluoro-pyrrolidin-l-yl]-6-fluoro-l-[(IR,2S)-2-fluorocyclopropan-l-yl]-1,4-dihydro- 8-methyl-4-oxoquinolin-3-carboxylic acid), a new quinolone antibacterial agent for serious infections caused by Gram-positive pathogens. The key step was the intramolecular Homer-Wadsworth-Emmons reaction. In addition, the yield of the final aromatic micleophilic substitution reaction was improved.

  DOI：

  10.3987/com-03-9972
• 作为产物：
  描述：

  2-二乙基膦酰基-2-氟乙酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 18.0h， 生成 N-[(1-ethoxycarbonylcycloprop-1-yl)carbonylmethyl]-N-[(S)-1-phenylethyl]-2-(diethoxyphosphoryl)-2-fluoroacetamide
  参考文献：
  名称：

  Practical Synthesis of DQ-113, a New Quinolone Antibacterial Agent, by Using the Intramolecular Horner-Wadsworth- Emmons Reaction

  摘要：

  A practical route was developed for synthesizing the C-7 substituent of DQ-113 (6, 5-amino-7-[(3S,4R)-4-(1-aminocycloprop-l-yl)-3-fluoro-pyrrolidin-l-yl]-6-fluoro-l-[(IR,2S)-2-fluorocyclopropan-l-yl]-1,4-dihydro- 8-methyl-4-oxoquinolin-3-carboxylic acid), a new quinolone antibacterial agent for serious infections caused by Gram-positive pathogens. The key step was the intramolecular Homer-Wadsworth-Emmons reaction. In addition, the yield of the final aromatic micleophilic substitution reaction was improved.

  DOI：

  10.3987/com-03-9972

文献信息

• Practical Synthesis of DQ-113, a New Quinolone Antibacterial Agent, by Using the Intramolecular Horner-Wadsworth- Emmons Reaction
  作者：Hiroaki Inagaki、Toshiyuki Takeda、Rie N. Miyauchi、Katsuhiro Kawakami、Hisashi Takahashi、Makoto Takemura

  DOI：10.3987/com-03-9972

  日期：——

  A practical route was developed for synthesizing the C-7 substituent of DQ-113 (6, 5-amino-7-[(3S,4R)-4-(1-aminocycloprop-l-yl)-3-fluoro-pyrrolidin-l-yl]-6-fluoro-l-[(IR,2S)-2-fluorocyclopropan-l-yl]-1,4-dihydro- 8-methyl-4-oxoquinolin-3-carboxylic acid), a new quinolone antibacterial agent for serious infections caused by Gram-positive pathogens. The key step was the intramolecular Homer-Wadsworth-Emmons reaction. In addition, the yield of the final aromatic micleophilic substitution reaction was improved.