2-acetylthiophene-4-phenyl-3-thiosemicarbazone | 116873-13-3

• 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: 2-acetylthiophene-4-phenyl-3-thiosemicarbazone
• 英文别名: Hydrazinecarbothioamide, N-phenyl-2-[1-(2-thienyl)ethylidene]-；1-phenyl-3-(1-thiophen-2-ylethylideneamino)thiourea
• CAS: 116873-13-3
• 化学式: C₁₃H₁₃N₃S₂
• 分子量: 275.398
• InChiKey: YRGSGWYRBFTXOU-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C(Solv: ethanol (64-17-5); chloroform (67-66-3))
• 沸点：
  405.0±37.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dichloro(cycloocta-1,5-diene)palladium (II) 、 2-acetylthiophene-4-phenyl-3-thiosemicarbazone 以 乙醇 为溶剂， 以75%的产率得到[Pd(2-acetylthiophene-4-phenylthiosemicarbazone(-1H))Cl]
  参考文献：
  名称：

  Platinum and palladium complexes of thiosemicarbazones derived of 2-acetylthiophene: Synthesis and spectral studies

  摘要：

  The reaction of 2-acetylthiophene thiosemicarbazone (2-HATT) and 2-acetylthiophene 4-phenylthiosemicarbazone (2-HAT-4-FT) with Pd(COD)Cl-2 (COD = 1,5-cyclooctadiene) and tranS-Pt2PEt3Cl4 yielded four new metal complexes: [Pd(2-HATT)Cl-2] (1), [Pd(2-ATT)(2)] (2), [Pd(2-AT-4-Fr)Cl] (3) and [Pt(2-ATT)(PEt3)Cl] (4). Apart from compound 3 all the others were characterised by H-1 and C-13{1H} NMR, infrared spectroscopy, and elemental analysis. Multinuclear NMR experiments of P-31{H-1} and Pt-195{H-1} of complex 4 have revealed that the ligand 2-HATT behaves as a bidentate chelating agent towards Pd(COD)Cl-2 and trans-Pt2PEt3Cl4 whereas ligand 2-HAT-4-Fr forms a tridentate chelating complex with Pd(COD)Cl-2. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2005.06.016
• 作为产物：
  描述：

  2-乙酰基噻吩 以 乙醇 、 异丙醇 为溶剂， 生成 2-acetylthiophene-4-phenyl-3-thiosemicarbazone
  参考文献：
  名称：

  Synthesis and anticancer activity of thiosemicarbazones

  摘要：

  Twenty-six thiosemincarbazones (III-1-III-26) were synthesized via three steps starting from hydrazine hydrate and carbon disulfide. The testing of anticancer activity of these compounds in vitro against P-388, A-549, and SGC-7901 shows that compounds III-15 and III-16 possess a higher inhibitory ability for P-388 and SGC-7901. Further testing shows that the value of IC50 of compound III-16 against SGC-7901 reaches to 0.032 mu M. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.048

文献信息

• Thiosemicarbazone derivatives of nickel and copper: the unprecedented coordination of furan ring in octahedral nickel(ii) and of triphenylphosphine in three-coordinate copper(i) complexes
  作者：Tarlok Singh Lobana、Poonam Kumari、Rekha Sharma、Alfonso Castineiras、Ray Jay Butcher、Takashiro Akitsu、Yoshikazu Aritake

  DOI：10.1039/c0dt01291b

  日期：——

  The influence of substituents at the C2carbon of N1-substituted thiosemicarbazones, C4H3X–C2(CH3)N3–N2H–C1(S)N1HR2} (X = O, S) on the geometry of nickel(II) complexes has been investigated. The presence of a methyl group at the C2 position of 2-acetylfuran-N1-substituted thiosemicarbazones (C4H3O)–C2(CH3)N3–N2H–C1(S)N1HR2, R2 = CH3, HaftscN–Me; C2H5, HaftscN–Et; C6H5, HaftscN–Ph} induces unusual

  取代基对N 1取代的硫代半氨基甲酮C 4 H 3 X–C 2（CH 3）N 3 –N 2 H–C 1（S）N 1 HR 2 }的C 2碳的影响（X = O ，S）对镍（II）配合物的几何形状进行了研究。在2-乙酰基呋喃-N 1取代的硫代半氨基偶氮C 4 H 3 O）–C 2（CH 3）N 3 –N的C 2位置存在甲基2 H–C 1（S）N 1 HR 2，R 2 = CH 3，HaftscN–Me；C 2 H 5，HaftscN-Et； m / z。Ç 6 ħ 5，HaftscN-PH}诱导由呋喃环，并且得到高自旋八面体镍异常协调（ II）配合物，[镍（κ 3 -O，N 3，S-aftscN-R 2） 2 ]，CH 3 1，C 2 ħ 5 2，和2 [的Ni（（κ 3 -O，N 3，S-aftscN-PH） 2 ] 3（μ EFF = 2.98，1 ; 2.96，2 ; 2.92，3）。使用2-乙酰基噻吩-N
• Thiosemicarbazonates of palladium(II): The presence of methyl/phenyl substituents (R2) at C2 carbon atom induces C–H activation of R1 rings of thiosemicarbazones {R1R2C2N3–N2H–C1(S)–N1HR3}
  作者：Tarlok S. Lobana、Poonam Kumari、Ray J. Butcher、Takashiro Akitsu、Yoshikazu Aritake、Josefina Perles、Francisco J. Fernandez、M. Cristina Vega

  DOI：10.1016/j.jorganchem.2011.11.028

  日期：2012.3

  A series of palladium(II) complexes involving C-H and N-H bond activations of the R-1 rings of thiosemicarbazones R-1(R-2)C-2-N-3-N-2(H)-C-1(=S)-(NHR3)-H-1; R-1, R-2: thiopheneyl, Me, H2L1 (R-3 = Me), H2L2 (R-3 = Ph); R-1, R-2: Ph, Me, H2L3 (R-3 = Me), H2L4 (R-3 = Ph); R-1, R-2: Ph, Ph, H2L5 (R-3 = Me), H2L6 (R-3 = Ph) and R-1, R-2: pyrrole, Me, H2L7 (R-3 = Me), H2L8 (R-3 = Ph)} are described. Methyl group (R-2) at C-2 carbon in H2L1 and H2L2 induced C-H bond activation of the thiopheneyl ring and formed cyclometallated complexes, [Pd(kappa(3)-C-4,N-3,S-L)(PPh3)] (L - L-1, 1; L-2, 2). Similarly, phenyl rings (R-1) in H2L3, H2L4, H2L5, H2L6 at C-2 carbon have shown C-H activations forming cyclometallated complexes, [Pd(kappa(3)-C-4,N-3, S-L)(PPh3)] (L = L-3, 3; L-4, 4; L-5, 5; L-6, 6). However, pyrrole ring did not exhibit similar C-H activation behavior, rather involved N-H activation and formed complexes, [Pd(kappa(3)-N-4,N-3, S-L)(PPh3)] L = L-7, 7; L-8, 8}. All these complexes have been characterized with the help of analytical data, spectroscopic techniques (IR, H-1 and P-31 NMR), and single crystal X-ray crystallography (1, 2, 4, 5, 7 and 8). The thiosemicarbazone ligands behave as dinegative C-4, N-3, S-chelating in 1-6 and N-4, N-3, S-chelating in complexes 7 and 8. Interestingly, complexes 2, 4 and 8, with phenyl substituent at N-1 atom, have two independent molecules in their respective crystal lattices. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis, structure and spectroscopy of mono- and di-nuclear copper(I) complexes incorporating anionic thiophene based thiosemicarbazones-first examples
  作者：Tarlok S. Lobana、Shikha Indoria、Manvi Sharma、Jyoti Nandi、Amanpreet K. Jassal、Maninder S. Hundal、Alfonso Castineiras

  DOI：10.1016/j.poly.2014.01.002

  日期：2014.9
• Prasad; Reddy, K. Hussain; Reddy, T. Sreenivasulu, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2003, vol. 42, # 1, p. 112 - 115
  作者：Prasad、Reddy, K. Hussain、Reddy, T. Sreenivasulu

  DOI：——

  日期：——
• Synthesis and anticancer activity of thiosemicarbazones
  作者：Wei-xiao Hu、Wei Zhou、Chun-nian Xia、Xi Wen

  DOI：10.1016/j.bmcl.2006.01.048

  日期：2006.4

  Twenty-six thiosemincarbazones (III-1-III-26) were synthesized via three steps starting from hydrazine hydrate and carbon disulfide. The testing of anticancer activity of these compounds in vitro against P-388, A-549, and SGC-7901 shows that compounds III-15 and III-16 possess a higher inhibitory ability for P-388 and SGC-7901. Further testing shows that the value of IC50 of compound III-16 against SGC-7901 reaches to 0.032 mu M. (C) 2006 Elsevier Ltd. All rights reserved.