5-tert-butyl-2-thienylacetic acid | 943756-21-6

• 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: 5-tert-butyl-2-thienylacetic acid
• 英文别名: 2-(5-Tert-butylthiophen-2-yl)acetic acid
• CAS: 943756-21-6
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: IRKZGKTYBKDNAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-2-thienylacetic acid 在 sodium acetate 、 silver carbonate 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 2-[5-Tert-butyl-2-(1-hydroxy-3-oxophenalen-2-yl)thiophen-3-yl]-2-(5-tert-butylthiophen-2-yl)phenalene-1,3-dione
  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 在 氢氧化钾 、 三氯化铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 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

文献信息

• ARYL HYDROCARBON RECEPTOR MODULATOR
  申请人：Ariagen, Inc.

  公开号：US20190307731A1

  公开（公告）日：2019-10-10

  Disclosed is an aryl hydrocarbon receptor modulator of formula (I), and a pharmaceutically acceptable salt thereof, wherein R′ is H, CN, CH 2 (OH)R 0 , C m H 2m+1 , C n H 2n-1 , C n H 2n-3 , two R a are independently H or two R a together form ═O or ═N—W 3 —R 1 ; A is a C 6 to C 10 aromatic ring unsubstituted or substituted with 1 to 3 R, or a C 2 -C 10 heteroaromatic ring interrupted by 1 to 5 heteroatoms selected from N, O, and S or a 4 to 7 membered nonaromatic heterocyclic ring containing C═N and interrupted by 1 to 3 heteroatoms selected from N, O, and S, with either one unsubstituted or substituted with 1 to 3 R; Q is R, or is a C 6 to C 10 aromatic ring or a C 2 to C 10 heteroaromatic ring unsubstituted or substituted with 1 to 3 R and interrupted by 1 to 5 heteroatoms selected from N, O, and S; and R is R c which is C-attached or R N which is N-attached. The compounds of formula (I) of the present invention can regulate AhR activity, and can be used to inhibit the growth of cancer cells and inhibit the metastasis and invasion of tumor cells.

  本发明揭示了一种化学式（I）的芳香烃受体调节剂及其药用可接受盐，其中R′为H、CN、CH2（OH）R0、CmH2m+1、CnH2n-1、CnH2n-3，两个Ra独立地为H或两个Ra共同形成═O或═N—W3—R1；A为未取代或取代1至3个R的C6至C10芳香环，或由N、O和S中选择的1至5个杂原子中断的C2-C10杂芳环，或含有C═N并由N、O和S中选择的1至3个杂原子中断的4至7个成员的非芳杂环，其中一个未取代或取代1至3个R；Q为R，或者是未取代或取代1至3个R并由N、O和S中断的C6至C10芳香环或C2至C10杂芳环；R为C-连接的Rc或N-连接的RN。本发明的化合物可以调节AhR活性，可用于抑制癌细胞的生长，以及抑制肿瘤细胞的转移和侵袭。
• 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.