ethyl 5-oxo-6-azatricyclo<4.3.1^2,9.0>dec-3-ene-endo-10-carboxylate | 143706-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: ethyl 5-oxo-6-azatricyclo<4.3.1^2,9.0>dec-3-ene-endo-10-carboxylate
• 英文别名: ethyl (1R,2S,3S,10S)-7-oxo-6-azatricyclo[4.3.1.03,10]dec-8-ene-2-carboxylate
• CAS: 143706-12-1
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: UZCMSLQTTMKSPC-JZSSXWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-<4-(ethoxycarbonyl)-3-trans-butenyl>-2-pyridone 在 二苯甲酮 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到ethyl 5-oxo-6-azatricyclo<4.3.1^2,9.0>dec-3-ene-endo-10-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

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.