(Diethoxy-phosphoryl)-[2-[1,3]dioxolan-2-ylmethyl-prop-2-en-(Z)-ylideneamino]-acetic acid methyl ester | 100366-91-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Diethoxy-phosphoryl)-[2-[1,3]dioxolan-2-ylmethyl-prop-2-en-(Z)-ylideneamino]-acetic acid methyl ester
• CAS: 100366-91-4
• 化学式: C₁₄H₂₄NO₇P
• 分子量: 349.321
• InChiKey: ITLQUMANJCJAQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  23.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  92.65
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (Diethoxy-phosphoryl)-[2-[1,3]dioxolan-2-ylmethyl-prop-2-en-(Z)-ylideneamino]-acetic acid methyl ester 在 硫酸 、 三乙胺 作用下， 以 环己烷 、 溶剂黄146 、 苯 为溶剂， 反应 4.0h， 生成 (+/-)-1-<(methoxycarbonyl)(diethylphosphono)methyl>-3-azido-4-(3-oxo-1-methylprop-1-enyl)-2-azetidinone
  参考文献：
  名称：

  Synthesis of .DELTA.3-1-methylene-1-carbacephems

  摘要：

  The total synthesis of (+/-)-1-methylene-2,2- dimethyl-7-amino-1-carbacephem-4-carboxylic acid (1) is described. The reaction scheme was essentially that described by Christensen et al. for the synthesis of (+/-)-1-carbacephems. In vitro antibacterial activities of the 7-phenoxyacetyl and 7-D-alpha-phenylglycyl derivatives of 1 were compared with those of 7-(phenoxyacetamido)desacetoxycephalosporanic acid and cefalexin. Derivatives of 1 were 2-4 times less active against most of the sensitive organisms than the corresponding 7-aminodesacetoxycephalosporanic acid analogues. The activity of the 7-D-alpha-phenylglycyl derivative of 1 however was about 20 times lower than that of cefalexin when measured against Staphylococcus aureus ATCC 6538P.

  DOI：

  10.1021/jm00155a013
• 作为产物：
  描述：

  1,3-二氧戊环-2-丙-1-醇 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 (Diethoxy-phosphoryl)-[2-[1,3]dioxolan-2-ylmethyl-prop-2-en-(Z)-ylideneamino]-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of .DELTA.3-1-methylene-1-carbacephems

  摘要：

  The total synthesis of (+/-)-1-methylene-2,2- dimethyl-7-amino-1-carbacephem-4-carboxylic acid (1) is described. The reaction scheme was essentially that described by Christensen et al. for the synthesis of (+/-)-1-carbacephems. In vitro antibacterial activities of the 7-phenoxyacetyl and 7-D-alpha-phenylglycyl derivatives of 1 were compared with those of 7-(phenoxyacetamido)desacetoxycephalosporanic acid and cefalexin. Derivatives of 1 were 2-4 times less active against most of the sensitive organisms than the corresponding 7-aminodesacetoxycephalosporanic acid analogues. The activity of the 7-D-alpha-phenylglycyl derivative of 1 however was about 20 times lower than that of cefalexin when measured against Staphylococcus aureus ATCC 6538P.

  DOI：

  10.1021/jm00155a013