ethyl 5-tert-butyl-2-thienylacetate | 943756-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 5-tert-butyl-2-thienylacetate
• 英文别名: ethyl 2-(5-tert-butylthiophen-2-yl)acetate
• CAS: 943756-20-5
• 化学式: C₁₂H₁₈O₂S
• 分子量: 226.34
• InChiKey: DFWACDPQWYEFPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-tert-butyl-2-thienylacetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 9.0h， 以100%的产率得到5-tert-butyl-2-thienylacetic acid
  参考文献：
  名称：

  Control in spin-delocalization into the 2-substituted π-systems in 3-oxophenalenoxyl neutral radicals: evaluation by their dimeric structures and DFT calculations

  摘要：

  3-Oxophenalenoxyl derivatives, neutral pi-radicals having two oxygen atoms at 1,3-position on a phenalenyl skeleton, possess most of their spin densities at the two oxygen atoms and the 2-position, featuring in easy dimerization at the 2-position. For the decrease in spin density at the 2-position by invoking spin-delocalization into the 2-substituted p-systems, we have designed 2-thienyl-3-hydroxyphenalenone derivatives as synthetic precursors of neutral p-radicals, and conducted their oxidation reactions by using a variety of oxidants. The chemical structures of the dimer obtained were unambiguously determined by FABMS, IR, and NMR spectra with help of density functional theory calculations, showing the formation of the bonds on the thienyl moieties. These observations and DFT calculations illustrate the occurrence of a considerable amount of spin-delocalization into the 2-substituted-thienyl moieties from the 3-oxophenalenoxyl skeletons. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.018
• 作为产物：
  描述：

  2-噻吩乙酸乙酯 、 氯代叔丁烷 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到ethyl 5-tert-butyl-2-thienylacetate
  参考文献：
  名称：

  Control in spin-delocalization into the 2-substituted π-systems in 3-oxophenalenoxyl neutral radicals: evaluation by their dimeric structures and DFT calculations

  摘要：

  3-Oxophenalenoxyl derivatives, neutral pi-radicals having two oxygen atoms at 1,3-position on a phenalenyl skeleton, possess most of their spin densities at the two oxygen atoms and the 2-position, featuring in easy dimerization at the 2-position. For the decrease in spin density at the 2-position by invoking spin-delocalization into the 2-substituted p-systems, we have designed 2-thienyl-3-hydroxyphenalenone derivatives as synthetic precursors of neutral p-radicals, and conducted their oxidation reactions by using a variety of oxidants. The chemical structures of the dimer obtained were unambiguously determined by FABMS, IR, and NMR spectra with help of density functional theory calculations, showing the formation of the bonds on the thienyl moieties. These observations and DFT calculations illustrate the occurrence of a considerable amount of spin-delocalization into the 2-substituted-thienyl moieties from the 3-oxophenalenoxyl skeletons. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.018

文献信息

• Control in spin-delocalization into the 2-substituted π-systems in 3-oxophenalenoxyl neutral radicals: evaluation by their dimeric structures and DFT calculations
  作者：Shinsuke Nishida、Yasushi Morita、Tomohiro Ohba、Kozo Fukui、Kazunobu Sato、Takeji Takui、Kazuhiro Nakasuji

  DOI：10.1016/j.tet.2007.05.018

  日期：2007.8

  3-Oxophenalenoxyl derivatives, neutral pi-radicals having two oxygen atoms at 1,3-position on a phenalenyl skeleton, possess most of their spin densities at the two oxygen atoms and the 2-position, featuring in easy dimerization at the 2-position. For the decrease in spin density at the 2-position by invoking spin-delocalization into the 2-substituted p-systems, we have designed 2-thienyl-3-hydroxyphenalenone derivatives as synthetic precursors of neutral p-radicals, and conducted their oxidation reactions by using a variety of oxidants. The chemical structures of the dimer obtained were unambiguously determined by FABMS, IR, and NMR spectra with help of density functional theory calculations, showing the formation of the bonds on the thienyl moieties. These observations and DFT calculations illustrate the occurrence of a considerable amount of spin-delocalization into the 2-substituted-thienyl moieties from the 3-oxophenalenoxyl skeletons. (C) 2007 Elsevier Ltd. All rights reserved.