o-(trifluoromethyl)benzeneseleninic acid | 149419-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: o-(trifluoromethyl)benzeneseleninic acid
• 英文别名: 2-trifluoromethylbenzeneseleninic acid；2-(trifluoromethyl)benzeneseleninic acid
• CAS: 149419-65-8
• 化学式: C₇H₅F₃O₂Se
• 分子量: 257.071
• InChiKey: DDXJQOXDHNZTKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  o-(trifluoromethyl)benzeneseleninic acid 在 偶氮二异丁腈 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 (Z)-2-((o-(trifluoromethyl)phenyl)seleno)-1-(p-toluenesulfonyl)-2-hexene
  参考文献：
  名称：

  Asymmetric selenoxide elimination leading to chiral allenic sulfones

  摘要：

  Asymmetric oxidation of some aryl vinyl selenides (3) with Sharpless (A-C), modified Sharpless (D) or David oxidants (E-G) resulted in the formation of chiral allenic sulfones 5 of up to 42% enantiomeric excess (ee) via double asymmetric induction, i.e., asymmetric oxidation to selenoxide followed by its asymmetric elimination. The nature of aryl group of the selenides 3 showed a remarkable effect upon the ee of the product: o-nitrophenyl group (a) gave the highest ee, followed by o,p-dinitrophenyl (b), o-(trifluoromethyl)phenyl (e), and o-methoxyphenyl (f) groups, while phenyl (e) and 2-pyridyl (d) groups were not effective at all. The effects of aryl groups were kinetically analyzed by comparing the rate constants of both steps (k1 for oxidation step and k2 for elimination step) which were determined by H-1-NMR analysis of the concentration of 3, the intermediate selenoxides 4, and 5. As a result, it was disclosed that the ratio of these rate constants (k1/k2) Was closely related to the ee of the product; the smaller the ratio is, the larger the ee becomes.

  DOI：

  10.1021/jo00066a023
• 作为产物：
  描述：

  1,2-bis(2-(trifluoromethyl)phenyl)diselane 在 双氧水 作用下， 生成 o-(trifluoromethyl)benzeneseleninic acid
  参考文献：
  名称：

  Asymmetric selenoxide elimination leading to chiral allenic sulfones

  摘要：

  Asymmetric oxidation of some aryl vinyl selenides (3) with Sharpless (A-C), modified Sharpless (D) or David oxidants (E-G) resulted in the formation of chiral allenic sulfones 5 of up to 42% enantiomeric excess (ee) via double asymmetric induction, i.e., asymmetric oxidation to selenoxide followed by its asymmetric elimination. The nature of aryl group of the selenides 3 showed a remarkable effect upon the ee of the product: o-nitrophenyl group (a) gave the highest ee, followed by o,p-dinitrophenyl (b), o-(trifluoromethyl)phenyl (e), and o-methoxyphenyl (f) groups, while phenyl (e) and 2-pyridyl (d) groups were not effective at all. The effects of aryl groups were kinetically analyzed by comparing the rate constants of both steps (k1 for oxidation step and k2 for elimination step) which were determined by H-1-NMR analysis of the concentration of 3, the intermediate selenoxides 4, and 5. As a result, it was disclosed that the ratio of these rate constants (k1/k2) Was closely related to the ee of the product; the smaller the ratio is, the larger the ee becomes.

  DOI：

  10.1021/jo00066a023

文献信息

• Syntheses and structural characterization of organotin complexes derived from 2-(trifluoromethyl)benzeneseleninic acid: tetranuclear macrocycle, 1-D polymeric chain, helical double-chain
  作者：Ru-Fen Zhang、Fei Wang、Qian-Li Li、Shao-Liang Zhang、Chun-Lin Ma

  DOI：10.1080/00958972.2015.1124989

  日期：2016.2.16

  Abstract Four organotin(IV) complexes based on 2-(trifluoromethyl)benzeneseleninic acid, [Me3Sn(O2SeC6H4-2-CF3)]4 (1), [Ph3Sn(O2SeC6H4-2-CF3)]n (2), [R2Sn(O2SeC6H4-2-CF3)2]n (R = Me 3; n-Bu 4), have been synthesized and characterized by X-ray diffraction, elemental analysis, infrared spectroscopy, and NMR (1H, 13C and 119Sn) spectroscopy. Single-crystal X-ray analyses show that 1 has a centrosymmetric

  摘要 四种基于 2-(三氟甲基)苯硒酸的有机锡 (IV) 配合物, [Me3Sn(O2SeC6H4-2-CF3)]4 (1), [Ph3Sn(O2SeC6H4-2- )]n (2), [R2Sn( O2SeC6H4-2- )2]n (R = Me 3; n-Bu 4)，已合成并通过 X 射线衍射、元素分析、红外光谱和 NMR（1H、13C 和 119Sn）光谱表征。单晶X射线分析表明，1具有中心对称的四核三有机锡亚硒酸盐，具有由三甲基锡和配体交替连接形成的四核16元大环；图2显示一维中性无限链结构，其中[O2SeC6H4-2- ]-是μ2-桥接配体；图 3 和图 4 是包含 Sn2O4Se2 八元环的聚合物链结构，其中芳硒酸基团是锡离子之间的双桥。对 1 的分子间接触的检查揭示了 C-H⋯O 氢键相互作用和 C-H⋯π 相互作用的存在。还发现弱的 C-H⋯O 相互作用对于 3 的