3-<3-(1,6-Dihydro-1-methyl-6-oxo-2-pyridinyl)propyl>-1-methyl-2(1H)-pyridone | 153943-09-0

• 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: 3-<3-(1,6-Dihydro-1-methyl-6-oxo-2-pyridinyl)propyl>-1-methyl-2(1H)-pyridone
• 英文别名: 1-Methyl-6-[3-(1-methyl-2-oxopyridin-3-yl)propyl]pyridin-2-one
• CAS: 153943-09-0
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: ZDCQEHPXEARVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-<3-(1,6-Dihydro-1-methyl-6-oxo-2-pyridinyl)propyl>-1-methyl-2(1H)-pyridone 生成 6,10-dimethyl-6,10-diazatetracyclo[7.2.2.25,8.01,5]pentadeca-12,14-diene-7,11-dione
  参考文献：
  名称：

  Sieburth Scott McN., Hiel Gary, Lin Chao-Hsiung, Kuan Dora P., J. Org. Chem, 59 (1994) N 1, S 80-87

  摘要：

  DOI：
• 作为产物：
  描述：

  6-[3-(2-oxo-1H-pyridin-3-yl)propyl]-1H-pyridin-2-one 、 碘甲烷 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 3-<3-(1,6-Dihydro-1-methyl-6-oxo-2-pyridinyl)propyl>-1-methyl-2(1H)-pyridone
  参考文献：
  名称：

  Intramolecular [4 + 4] photocycloaddition of 2-pyridones tethered by a three-carbon chain: studies on the formation of cycloadducts and control of stereogenesis. 3

  摘要：

  Irradiation of a pair of 2-pyridones tethered at the 3- and 6' positions by a three-carbon chain initiates an efficient [4+4] cycloaddition to produce a densely functionalized, fused 5-8 carbocyclic ring system with the trans isomer predominant. An asymmetric center on the tether influences stereogenesis at the four new tetrahedral centers. This effect was probed with an alcohol substituent and its silyl ether as a function of solvent. A combination of inter- and intramolecular hydrogen-bonding can account for the observed levels of selectivity. Some of the cis products are unstable and undergo Cope rearrangement, yielding cyclobutane isomers.

  DOI：

  10.1021/jo00080a015

文献信息

• Sieburth Scott McN., Hiel Gary, Lin Chao-Hsiung, Kuan Dora P., J. Org. Chem, 59 (1994) N 1, S 80-87
  作者：Sieburth Scott McN., Hiel Gary, Lin Chao-Hsiung, Kuan Dora P.

  DOI：——

  日期：——
• Stereocontrol of 2-Pyridone [4 + 4] Photocycloaddition: A Thermal-Photochemical Cycle To Produce Exclusively Trans Cycloadducts
  作者：Scott M. Sieburth、Chao-Hsiung Lin

  DOI：10.1021/jo00092a018

  日期：1994.7

  Intramolecular [4 + 4] photocycloaddition of 2-pyridones tethered by a three-carbon chain yield mixtures of trans and cis products. A general method is described for producing the trans isomer from the cis isomer by Cope rearrangement of the latter followed by photolysis. Photocleavage of the Cope product transiently reforms the tethered pyridones which then undergo a new [4 + 4] photocycloaddition. The trans isomer is inert to the reaction conditions and so the transformations can be performed without isolation steps. Two cycles of heating and irradiation transform an initial trans/cis ratio of 2:1 to nearly 20:1, with a corresponding increase in the yield of the trans isomer. Combination of this chemistry with control from a tether substituent allows for the facile synthesis of a single [4 + 4] product with five stereogenic centers.
• Intramolecular [4 + 4] photocycloaddition of 2-pyridones tethered by a three-carbon chain: studies on the formation of cycloadducts and control of stereogenesis. 3
  作者：Scott M. Sieburth、Gary Hiel、C.-H. Lin、Dora P. Kuan

  DOI：10.1021/jo00080a015

  日期：1994.1

  Irradiation of a pair of 2-pyridones tethered at the 3- and 6' positions by a three-carbon chain initiates an efficient [4+4] cycloaddition to produce a densely functionalized, fused 5-8 carbocyclic ring system with the trans isomer predominant. An asymmetric center on the tether influences stereogenesis at the four new tetrahedral centers. This effect was probed with an alcohol substituent and its silyl ether as a function of solvent. A combination of inter- and intramolecular hydrogen-bonding can account for the observed levels of selectivity. Some of the cis products are unstable and undergo Cope rearrangement, yielding cyclobutane isomers.