13-oxo-3,6,9-trioxa-15-azabicyclo[9.3.1]pentadeca-1(14),11-diene-12-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 13-oxo-3,6,9-trioxa-15-azabicyclo[9.3.1]pentadeca-1(14),11-diene-12-carboxylic acid
• 化学式: C₁₂H₁₅NO₆
• 分子量: 269.254
• InChiKey: BRENMMZYAYINLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,6,9-三噁十一烷二酸 在 吡啶 、 草酰氯 、 氨 作用下， 以 乙醇 、 二氯甲烷 、 氯苯 、 苯 为溶剂， 反应 88.0h， 生成 13-oxo-3,6,9-trioxa-15-azabicyclo[9.3.1]pentadeca-1(14),11-diene-12-carboxylic acid
  参考文献：
  名称：

  A New Method for Synthesis of Crown Ether Type Pyridinophanes

  摘要：

  Bis(acylketene) (3) thermally generated from Meldrum's acid derivative (2) underwent intramolecular [4+2] cycloaddition to produce bridged dehydroacetic acid derivative (4). Heating 4 with methylamine and ammonia afforded crown ether type pyridinophanes (5) and (6) (12-crown-4), respectively. Reaction of the ketene (3) with (ethylene glycol)s afforded macrolactones (11similar to13) in satisfactory yields. Molecular structures of 4 and 6 are discussed based on X-Ray crystallographic analysis.

  DOI：

  10.3987/com-03-9740

文献信息

• A New Method for Synthesis of Crown Ether Type Pyridinophanes
  作者：Masayuki Sato、Tsunehisa Oda、Ken-ichi Iwamoto、Satoshi Fujii

  DOI：10.3987/com-03-9740

  日期：——

  Bis(acylketene) (3) thermally generated from Meldrum's acid derivative (2) underwent intramolecular [4+2] cycloaddition to produce bridged dehydroacetic acid derivative (4). Heating 4 with methylamine and ammonia afforded crown ether type pyridinophanes (5) and (6) (12-crown-4), respectively. Reaction of the ketene (3) with (ethylene glycol)s afforded macrolactones (11similar to13) in satisfactory yields. Molecular structures of 4 and 6 are discussed based on X-Ray crystallographic analysis.