1-<(acryloyloxy)methyl>-2-pyridone | 143706-09-6

• 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: 1-<(acryloyloxy)methyl>-2-pyridone
• 英文别名: (2-Oxopyridin-1-yl)methyl prop-2-enoate
• CAS: 143706-09-6
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: RQUBPMFAYUUAMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  352.6±25.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基吡啶 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 1-<(acryloyloxy)methyl>-2-pyridone
  参考文献：
  名称：

  Intramolecular [2 + 2]photocycloadditions of 1-(.omega.-alkenyl)-2-pyridones possessing an ester group on the olefinic carbon chain

  摘要：

  Photochemical reactions of three kinds of 1-(omega-alkenyl)-2-pyridones 1-8 were investigated. Photosensitized cycloadditions of 1-(omega-alkenyl)-2-pyridones and 1,3-bis(omega-alkenyl)-2-pyridone 2-6 afforded intramolecutar [2 + 2]cycloadducts across the 5,6-bonds of the 2-pyridones to give the tricyclic lactams 14-18: the additions were site-, regio-, and stereospecific. The yields of the adducts diminished in proportion to increased side-chain length. The one possessing the shortest alkenyl group, 1, and the 1-[omega-(acryloyloxy)alkyl]-2-pyridones 7 and 8, however, gave no products. On the other hand, direct irradiation of 3 afforded a bicyclic lactam 19. The intramolecular cycloaddition mechanism was discussed in terms of the excited state of 2-pyridone, as calculated by the MNDO-CI method.

  DOI：

  10.1021/jo00047a025

文献信息

• Intramolecular [2 + 2]photocycloadditions of 1-(.omega.-alkenyl)-2-pyridones possessing an ester group on the olefinic carbon chain
  作者：Kenichi Somekawa、Hiroyuki Okuhira、Masayuki Sendayama、Takaaki Suishu、Tetsuro Shimo

  DOI：10.1021/jo00047a025

  日期：1992.10

  Photochemical reactions of three kinds of 1-(omega-alkenyl)-2-pyridones 1-8 were investigated. Photosensitized cycloadditions of 1-(omega-alkenyl)-2-pyridones and 1,3-bis(omega-alkenyl)-2-pyridone 2-6 afforded intramolecutar [2 + 2]cycloadducts across the 5,6-bonds of the 2-pyridones to give the tricyclic lactams 14-18: the additions were site-, regio-, and stereospecific. The yields of the adducts diminished in proportion to increased side-chain length. The one possessing the shortest alkenyl group, 1, and the 1-[omega-(acryloyloxy)alkyl]-2-pyridones 7 and 8, however, gave no products. On the other hand, direct irradiation of 3 afforded a bicyclic lactam 19. The intramolecular cycloaddition mechanism was discussed in terms of the excited state of 2-pyridone, as calculated by the MNDO-CI method.