1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-,2-[(4-methoxyphenyl)methyl] 1-(2-propenyl) ester, (2S,4R)- | 654638-64-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-,2-[(4-methoxyphenyl)methyl] 1-(2-propenyl) ester, (2S,4R)-
• 英文别名: (2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-allyl ester 2-(4-methoxy-benzyl) ester
• CAS: 654638-64-9
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: ORRYCSZSWRTBCH-HIFRSBDPSA-N

物化性质

• 沸点：
  475.0±45.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-,2-[(4-methoxyphenyl)methyl] 1-(2-propenyl) ester, (2S,4R)- 在 sodium hydroxide 、 TEA 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 苯甲醚 、 乙腈 为溶剂， 反应 5.5h， 生成 (2S,4S)-4-Mercapto-2-{3-[(Z)-methoxyimino]-pyrrolidine-1-carbonyl}-pyrrolidine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Synthesis and biological activity of novel 1β-Methylcarbapenems with oxyiminopyrrolidinylamide moiety

  摘要：

  The synthesis and antibacterial activity of novel 1beta-methylcarbapenems 1a-f bearing oxyiminopyrrolidinylamide moiety at C-5 position of pyrrolidine are described. Most compounds exhibited comparable antibacterial activity to meropenem against a wide range of Gram-positive and Gram-negative organisms including Pseudomonas aeruginosa isolates. Of these carbapenems, 1a showed potent and broad spectrum of antibacterial activity and similar stability to DHP-I to meropenem. Against clinical isolates of 40 Gram-negative bacterial species including MDR and ESBL-producing strains, the selected carbapenem 1a possessed excellent in vitro activity except for MDR P. aeruginosa, and was comparable in potency to meropenem. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.039
• 作为产物：
  描述：

  L-羟基脯氨酸 在 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-,2-[(4-methoxyphenyl)methyl] 1-(2-propenyl) ester, (2S,4R)-
  参考文献：
  名称：

  Synthesis and biological activity of novel 1β-Methylcarbapenems with oxyiminopyrrolidinylamide moiety

  摘要：

  The synthesis and antibacterial activity of novel 1beta-methylcarbapenems 1a-f bearing oxyiminopyrrolidinylamide moiety at C-5 position of pyrrolidine are described. Most compounds exhibited comparable antibacterial activity to meropenem against a wide range of Gram-positive and Gram-negative organisms including Pseudomonas aeruginosa isolates. Of these carbapenems, 1a showed potent and broad spectrum of antibacterial activity and similar stability to DHP-I to meropenem. Against clinical isolates of 40 Gram-negative bacterial species including MDR and ESBL-producing strains, the selected carbapenem 1a possessed excellent in vitro activity except for MDR P. aeruginosa, and was comparable in potency to meropenem. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.039