2-acetylthiophene-N-methylthiosemicarbazone | 316159-38-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-acetylthiophene-N-methylthiosemicarbazone
• 英文别名: thiophene-2-acetaldehyde-N-methyl thiosemicarbazone；2-acetylthiophene-N(1)-methylthiosemicarbazone；acetylthiophene 4-methylthiosemicarbazone；HattscN-Me；1-Methyl-3-(1-thiophen-2-ylethylideneamino)thiourea；1-methyl-3-(1-thiophen-2-ylethylideneamino)thiourea
• CAS: 316159-38-3
• 化学式: C₈H₁₁N₃S₂
• 分子量: 213.327
• InChiKey: IENHATQPIVISIL-UHFFFAOYSA-N

物化性质

• 沸点：
  313.4±34.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2-acetylthiophene-N-methylthiosemicarbazone 在 NaOAc 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 Pd(acetylthiophene 4-methylthiosemicarbazone)(PPh3)
  参考文献：
  名称：

  噻吩取代的硫代半氨基甲酮的环钯缩合

  摘要：

  在碱的存在下，由硫代氨基脲或4,4'-二甲基硫代氨基脲与2-乙酰基噻吩的缩合反应获得的硫代氨基脲与K 2 PdCl 4反应，以高收率得到深色的难溶物质。用Ph 3 P，dppe或dppf处理这些低聚化合物可得到单体钯（II）膦配合物，其中去质子化的硫代半氨基甲酮通过C3环金属化的噻吩环，亚胺氮原子和硫原子以三齿形与金属配位。通过几种衍生物的X射线结构分析证实了这种配位模式。

  DOI：

  10.1016/j.jorganchem.2011.06.021
• 作为产物：
  描述：

  2-乙酰基噻吩 、 4-甲基氨基硫脲 在 溶剂黄146 作用下， 以89.65 %的产率得到2-acetylthiophene-N-methylthiosemicarbazone
  参考文献：
  名称：

  一些含五元环缩氨基硫脲的合成、表征及 Hirshfeld 表面分析

  摘要：

  摘要 作为多齿配体的缩氨基硫脲被认为是最重要的一类有机化合物，因为它们具有广谱的药理作用和易于与金属离子配位的能力。四种缩氨基硫脲，呋喃-2-甲醛-N-甲基缩氨基硫脲 ( Hfmtsc )、噻吩-2-乙醛缩氨基硫脲 ( Hattsc )、噻吩-2-乙醛-N-甲基缩氨基硫脲 ( Hatmtsc ) 和噻吩-2-乙醛-N-乙基使用取代的醛和（未）取代的氨基硫脲通过缩合反应成功制备了氨基硫脲（Hatetsc ）。它们通过熔点、元素分析、摩尔电导率、FTIR、UV-Vis、1H 和13 C NMR 光谱技术。它们的晶体结构是通过使用单晶X射线衍射研究确定的。通过 Hirshfeld 表面分析研究分子间相互作用。化合物的分子结构通过 N–H⋯S、C–H⋯S、N–H⋯O 和 C–H⋯O 相互作用来稳定。在每个化合物中，分子通过成对的 N-H⋯S 相互作用连接成\(R_{2}^{2}(8)\)二聚体。

  DOI：

  10.1134/s0022476623050013

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
• Heteroleptic six-coordinate bismuth(<scp>iii</scp>) complexes with 2-acetylthiophene thiosemicarbazones: synthesis, characterization, and biological properties
  作者：Ibrahim I. Ozturk、Kadriye Turk、Anita M. Grześkiewicz、Maciej Kubicki、Christina N. Banti、Sotiris K. Hadjikakou

  DOI：10.1039/d3nj01411h

  日期：——

  including their X-ray crystal structures. In all cases, the thiosemicarbazone ligand coordinated in a monodentate mode via the sulfur atom. Complexes 1 and 2 are mononuclear bismuth(III) complexes with octahedral (Oh) geometry around the metal ion formed by three sulfur and three chlorine atoms. However, the coordination mode of the ligands varied around the bismuth centers. Complex 1 contains one molecule

  The present study aimed to prepare and then evaluate the antiproliferative and antibacterial activities of bismuth(III) thiosemicarbazone complexes. Five bismuth(III) halide complexes of general formulae [BiX3(HL)3] (X: Cl; 1 and 2) and [BiX2(μ2-X)(HL)2]2 (X: Br and I; 3,4 and 5), where HL is a thiosemicarbazone bearing an acetylthiophene moiety, have been synthesized and fully characterized, including
• 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.
• Cyclopalladation of thiophene-substituted thiosemicarbazones
  作者：Henning Weiss、Fabian Mohr

  DOI：10.1016/j.jorganchem.2011.06.021

  日期：2011.10

  The thiosemicarbazones obtained from the condensation of thiosemicarbazide or 4,4′-dimethylthiosemicarbazide with 2-acetylthiophene react with K2PdCl4 in the presence of a base to give dark, poorly soluble materials in high yields. Treatment of these oligomeric compounds with Ph3P, dppe or dppf gives monomeric palladium(II) phosphine complexes in which the deprotonated thiosemicarbazones coordinate

  在碱的存在下，由硫代氨基脲或4,4'-二甲基硫代氨基脲与2-乙酰基噻吩的缩合反应获得的硫代氨基脲与K 2 PdCl 4反应，以高收率得到深色的难溶物质。用Ph 3 P，dppe或dppf处理这些低聚化合物可得到单体钯（II）膦配合物，其中去质子化的硫代半氨基甲酮通过C3环金属化的噻吩环，亚胺氮原子和硫原子以三齿形与金属配位。通过几种衍生物的X射线结构分析证实了这种配位模式。
• Synthesis, Characterization and Hirshfeld Surface Analysis of Some Thiosemicarbazones Containing a Five-Membered Ring
  作者：Ibrahim I. Ozturk

  DOI：10.1134/s0022476623050013

  日期：2023.5

  Abstract Thiosemicarbazones, which are multidentate ligands, are considered as one of the most important classes of organic compounds due to their broad spectrum of pharmacological effects and their ability to coordinate easily with metal ions. Four thiosemicarbazones, furan-2-carbaldehyde-N-methyl thiosemicarbazone (Hfmtsc), thiophene-2-acetaldehyde thiosemicarbazone (Hattsc), thiophene-2-acetaldehyde-N-methyl

  摘要 作为多齿配体的缩氨基硫脲被认为是最重要的一类有机化合物，因为它们具有广谱的药理作用和易于与金属离子配位的能力。四种缩氨基硫脲，呋喃-2-甲醛-N-甲基缩氨基硫脲 ( Hfmtsc )、噻吩-2-乙醛缩氨基硫脲 ( Hattsc )、噻吩-2-乙醛-N-甲基缩氨基硫脲 ( Hatmtsc ) 和噻吩-2-乙醛-N-乙基使用取代的醛和（未）取代的氨基硫脲通过缩合反应成功制备了氨基硫脲（Hatetsc ）。它们通过熔点、元素分析、摩尔电导率、FTIR、UV-Vis、1H 和13 C NMR 光谱技术。它们的晶体结构是通过使用单晶X射线衍射研究确定的。通过 Hirshfeld 表面分析研究分子间相互作用。化合物的分子结构通过 N–H⋯S、C–H⋯S、N–H⋯O 和 C–H⋯O 相互作用来稳定。在每个化合物中，分子通过成对的 N-H⋯S 相互作用连接成\(R_2}^2}(8)\)二聚体。