1-<5-(ethoxycarbonyl)-trans-4-pentenyl>-3-<<5-(ethoxycarbonyl)-trans-4-pentenyl>oxy>-2-pyridone | 143706-08-5

• 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-<5-(ethoxycarbonyl)-trans-4-pentenyl>-3-<<5-(ethoxycarbonyl)-trans-4-pentenyl>oxy>-2-pyridone
• 英文别名: 1-[5-(ethoxycarbonyl)-trans-4-pentenyl]-3-{[5-(ethoxycarbonyl)-trans-4-pentenyl]oxy}-2-pyridone；ethyl (E)-6-[3-[(E)-6-ethoxy-6-oxohex-4-enoxy]-2-oxopyridin-1-yl]hex-2-enoate
• CAS: 143706-08-5
• 化学式: C₂₁H₂₉NO₆
• 分子量: 391.464
• InChiKey: QDNMBTDMXVVOCA-FNCQTZNRSA-N

物化性质

• 沸点：
  577.9±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<5-(ethoxycarbonyl)-trans-4-pentenyl>-3-<<5-(ethoxycarbonyl)-trans-4-pentenyl>oxy>-2-pyridone 在 二苯甲酮 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以26%的产率得到ethyl 4-<<5-(ethoxycarbonyl)-trans-4-pentenyl>oxy>-5-oxo-6-azatricyclo<4.4.1^2,10.0>undec-3-ene-endo-11-carboxylate
  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
• 作为产物：
  描述：

  吡啶-2,3-二醇 、 (E)-ethyl 6-bromohex-2-enoate 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 43.0h， 以29%的产率得到1-<5-(ethoxycarbonyl)-trans-4-pentenyl>-3-<<5-(ethoxycarbonyl)-trans-4-pentenyl>oxy>-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.