3-<3-(1,6-Dihydro-6-oxo-2-pyridinyl)-1-((dimethyl(1,1-dimethylethyl)silyl)oxy)propyl>-2(1H)-pyridone | 1027580-78-4

• 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-6-oxo-2-pyridinyl)-1-((dimethyl(1,1-dimethylethyl)silyl)oxy)propyl>-2(1H)-pyridone
• 英文别名: 6-[3-[tert-butyl(dimethyl)silyl]oxy-3-(2-oxo-1H-pyridin-3-yl)propyl]-1H-pyridin-2-one
• CAS: 1027580-78-4
• 化学式: C₁₉H₂₈N₂O₃Si
• 分子量: 360.528
• InChiKey: NKWLICXURJAUTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<3-(1,6-Dihydro-6-oxo-2-pyridinyl)-1-((dimethyl(1,1-dimethylethyl)silyl)oxy)propyl>-2(1H)-pyridone 、 碘甲烷 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以57%的产率得到3-<3-(1,6-Dihydro-1-methyl-6-oxo-2-pyridinyl)-1-((dimethyl(1,1-dimethylethyl)silyl)oxy)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
• 作为产物：
  描述：

  2-氯烟酸 在 Lindlar's catalyst 、 镍 咪唑 、 sodium tetrahydroborate 、 乙烯基溴化镁 、 氢气 、 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 75.0 ℃ 、101.33 kPa 条件下， 反应 62.25h， 生成 3-<3-(1,6-Dihydro-6-oxo-2-pyridinyl)-1-((dimethyl(1,1-dimethylethyl)silyl)oxy)propyl>-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

• 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.