1-(4-ethylphenyl)-2-thiocyanatoethan-1-one | 6097-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-ethylphenyl)-2-thiocyanatoethan-1-one
• 英文别名: 4-Ethyl-ω-thiocyanato-acetophenon；1-(4-ethyl-phenyl)-2-thiocyanato-ethanone；1-(4-Aethyl-phenyl)-2-thiocyanato-aethanon；2-(4-Ethylphenyl)-2-oxoethyl thiocyanate；[2-(4-ethylphenyl)-2-oxoethyl] thiocyanate
• CAS: 6097-24-1
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: KBGXHXAIQMYCFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-ethylphenyl)-2-thiocyanatoethan-1-one 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 2-Chlor-4-(4-ethylphenyl)thiazol
  参考文献：
  名称：

  Studies in Thiazoles. V. Synthesis of Some 2-Chloro- and 2-Hydroxythiazoles

  摘要：

  DOI：

  10.1021/jo01053a059
• 作为产物：
  描述：

  4-乙基苯乙炔 、 N-thiocyanatosuccinimide 在 甲醇 、 水 、 silver trifluoromethanesulfonate 、 sodium tetrachloroaurate(III) 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以78%的产率得到1-(4-ethylphenyl)-2-thiocyanatoethan-1-one
  参考文献：
  名称：

  Ag-Catalyzed Thiocyanofunctionalization of Terminal Alkynes To Access Alkynylthiocyanates and α-Thiocyanoketones

  摘要：

  Unprecedented one-pot thiocyanofunctionalizations of terminal alkynes to deliver alkynylthiocyanates and alpha-thiocyanoketones using a silver-catalyzed procedure or under silver/gold relay catalysis is reported. These synthetically valuable organothiocyanates are accessed in high efficiency, and their derivatization into a variety of valuable sulfur-containing heterocycles and sulfides has also been demonstrated.

  DOI：

  10.1021/acs.orglett.8b03162

文献信息

• A correlative IR, MS, 1H, 13C and 15N NMR and theoretical study of 4-arylthiazol-2(3H)-onesElectronic supplementary information (ESI) available: NMR data, including graphs; Cartesian coordinates for 3a and 4. See http://www.rsc.org/suppdata/p2/b1/b106322g/
  作者：Kalevi Pihlaja、Vladimir Ovcharenko、Erkki Kolehmainen、Katri Laihia、Walter M. F. Fabian、Heinz Dehne、Alexander Perjéssy、Marion Kleist、Joachim Teller、Zora Šusteková

  DOI：10.1039/b106322g

  日期：2002.1.23

  Sixteen 4-arylthiazol-2(3H)-ones (3) were synthesised by cyclisation of α-thiocyanatoacetophenones (1) in acid solution. They appear to prefer greatly the oxo tautomeric forms. In CCl4 solution an equilibrium between the free CO bond and a “dimeric” hydrogen-bonded form exists in which the latter predominates. Several IR and NMR (1H, 13C and 15N) spectral properties are shown to correlate with Hammett σ-values and/or atomic Mulliken charges and bond orders, the latter being estimated by PM3 or AM1 semiempirical methods. The electron-impact mass spectra were also recorded and the fragmentation mechanisms interpreted in terms of the energetics of the ionic species. In addition, the geometric and electronic properties of 4-phenylthiazol-2(3H)-one (3a) and the related benzothiazol-2(3H)-one (4) based on ab initio HF/6-31 G* calculations are compared with each other.

  通过在酸性溶液中环化α-硫氰基苯乙酮（1），合成了16种4-芳基噻唑-2(3H)-酮（3）。它们似乎更倾向于氧代互变异构形式。在CCl4溶液中，自由羰基键与“二聚”氢键形式之间存在平衡，其中后者占优势。有几种红外和核磁共振（1H、13C和15N）光谱特性与HAMmett σ值和/或原子Mulliken电荷及键级相关联，后者通过PM3或AM1半经验方法估算。还记录了电子冲击质谱，并根据离子物种的能量学解释了裂解机制。此外，基于从头算HF/6-31G*计算，比较了4-苯基噻唑-2(3H)-酮（3a）及相关苯并噻唑-2(3H)-酮（4）的几何和电子性质。
• Zimmermann, T.; Fischer, G. W.; Teller, J., Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 5, p. 723 - 730
  作者：Zimmermann, T.、Fischer, G. W.、Teller, J.、Dehne, H.、Olk, B.

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• Teller, J.; Dehne, H.; Zimmermann, T., Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 4, p. 453 - 460
  作者：Teller, J.、Dehne, H.、Zimmermann, T.、Fischer, G. W.、Olk, B.

  DOI：——

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