N,N'-(3,3'-dipyridyl)thiourea | 18440-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N'-(3,3'-dipyridyl)thiourea
• 英文别名: 1,3-di(pyridin-3-yl)thiourea；N,N'-bis(3-pyridyl)thiourea；1,3-di(3-pyridyl)thiourea；1,3-di-pyridin-3-yl-thiourea；N,N'-di-[3]pyridyl-thiourea；N,N'-Di-[3]pyridyl-thioharnstoff；1,3-dipyridin-3-ylthiourea
• CAS: 18440-28-3
• 化学式: C₁₁H₁₀N₄S
• 分子量: 230.293
• InChiKey: NOTRQWDALQNNRT-UHFFFAOYSA-N

物化性质

• 熔点：
  173-176 °C
• 沸点：
  395.1±40.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-(3,3'-dipyridyl)thiourea 、 copper(I) bromide 以 乙腈 为溶剂， 以90.7%的产率得到CuBr(N,N'-bis(3-pyridyl)thiourea)5
  参考文献：
  名称：

  Copper(I) complexes of heterocyclic thiourea ligands

  摘要：

  The coordination of heterocyclic thiourea ligands (L = N-(2-pyridyl)-N'-phenylthiourea (1), N-(2-pyridyl)-N'-methylthiourea (2), N-(3-pyridyl)-N'-phenylthiourea (3), N-(3-pyridyl)-N'-methylthiourea (4), N-(4-pyridyl)-N'-phenylthiourea (5), N-(2-pyrimidyl)-N'-phenylthiourea (6), N-(2-pyrimidyl)-N'-methylthiourea (7), N-(2-thiazolyl)-N'-methylthiourea (8), N-(2-benzothiazolyl)-N'-methylthiourea (9), N,N'-bis(2-pyridyl)thiourea (10) and N,N'-bis(3-pyridyl)thiourea (11)) with CuX (X = Cl, Br, I, NO3) has been investigated. CuX:L product stoichiometries of 1:1-1:5 were found, with 1:1 being most common. X-ray structures of four 3-coordinate mononuclear CuXL2 complexes (CuCl(6)(2), CuCl(7)(2), CuBr(6)(2), and CuBr(9)(2)) are reported. In contrast, CuBr(1)(2) is a 1D sulfur-bridged polymer. CuIL structures (L = 7, 8) are 1D chains with corner-sharing Cu-2(mu-I)(2) and Cu-2(mu-S)(2) units, and CuCl(10) is a 2D network having mu-Cl and N-/S-bridging L. Two [CuL2]NO3 structures are reported: a mononuclear 4-coordinate copper complex with chelating ligands (L = 10) and a 1D link-chain with N-/S-bridging L (L = 3). Two ligand oxidative cyclizations were encountered during crystallization. CuI crystallized with 6 to produce zigzag ladder polymer [(CuI)(2)(12)]center dot 1/2CH(3)CN (12=N-(pyrimidin-2-yl)benzo[d]thiazol-2-amine) and CuNO3 crystallized with 10 to form [Cu-2(NO3)(13)(2)(MeCN)]NO3 (13 = dipyridyltetraazathiapentalene). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.08.023
• 作为产物：
  描述：

  3-氨基吡啶 、 二(1-苯并三唑基)甲硫酮 以 四氢呋喃 为溶剂， 反应 5.0h， 以83%的产率得到N,N'-(3,3'-dipyridyl)thiourea
  参考文献：
  名称：

  Benzotriazole-Assisted Thioacylation

  摘要：

  Benzotriazole reagents for thioacylation (RCSBt), thiocarbamoylation (RR'NCSBt), aryl/alkoxythioacylation (ROCSBt), and aryl/alkylthiothioacylation (RSCSBt) are synthesized, and their utility is assessed by syntheses of representative heteroaryl thioureas 3a-g, thioamides 15a-s, thionoesters 16a-h, thiocarbamates 17a-e, dithiocarbamates 18a-d, thiocarbonates 19a-c, and dithiocarbonates 20a-c.

  DOI：

  10.1021/jo050670t

文献信息

• Molecular conformation ofN,N′-diarylthioureas: An assessment by1H NMR and infrared spectroscopy
  作者：L. V. Sudha、S. Manogaran、D. N. Sathyanarayana

  DOI：10.1002/mrc.1260230802

  日期：1985.8

  Several N,N′‐dipyridyl‐ and N‐phenyl‐N′‐pyridyl‐thioureas were examined in different solvents at various temperatures by 1H NMR in order to study their conformational properties. The influence of concentration and the methyl substituent in the pyridine ring on the chemical shifts of the NH and pyridine groups was investigated. The observed chemical shifts are analysed in terms of the conformational properties

  通过 1H NMR 在不同溶剂中在不同温度下检测了几种 N,N'-二吡啶基和 N-苯基-N'-吡啶基硫脲，以研究它们的构象特性。研究了浓度和吡啶环中的甲基取代基对NH和吡啶基团化学位移的影响。根据分子的构象特性分析观察到的化学位移。已经确定了关于 CN 键的内部旋转的自由能障碍。已测量红外光谱以补充核磁共振研究。分子内氢键在吡啶硫脲的优选构象中起主要作用。数据进一步揭示了对称 N 中发生的有趣的动态交换现象，
• Hydrogen-Bonding Networks in Heterocyclic Thioureas
  作者：Aakarsh Saxena、Robert D. Pike

  DOI：10.1007/s10870-007-9246-1

  日期：2007.10.22

  heterocyclic thioureas from heterocyclic amines with phenyl- or methylisothiocyanate or CS2 is described. Seven new X-ray crystal structures are reported: In N-(3-pyridyl)-N′-phenylthiourea (Pna21, a = 10.1453(3), b = 17.6183(5), c = 6.4787(2), V = 1158.02(6), Z = 4) hydrogen-bonding results in formation of a 3D network consisting of helices, which form channels parallel to the c-axis. In N-(4-pyridyl)-N′-phenylthiourea

  摘要描述了杂环胺与异硫氰酸苯酯或甲基异硫氰酸酯或 CS2 合成杂环硫脲。报告了七种新的 X 射线晶体结构：在 N-(3-吡啶基)-N'-苯基硫脲 (Pna21, a = 10.1453(3), b = 17.6183(5), c = 6.4787(2), V = 1158.02) (6), Z = 4) 氢键导致形成由螺旋组成的 3D 网络，螺旋形成平行于 c 轴的通道。在 N-(4-吡啶基)-N'-苯基硫脲 (P21/c, a = 16.9314(3), b = 10.3554(2), c = 13.5152(3), β = 106.5080(10), V = 2271.96( 8), Z = 4, 两个独立的分子) 氢键导致 N–H…S 桥接二聚体和 N–H…Py 链，形成二维片状网络。在 N-(2-嘧啶基)-N'-苯基硫脲 (P21/c, a = 5.45900(10), b = 13
• 1H and13C nuclear magnetic resonance study of 1,3-dipyridylthioureas for chemical shift assignments and conformational analysis
  作者：L. V. Sudha、D. N. Sathyanarayana、S. Narasimha Bharati

  DOI：10.1002/mrc.1260250603

  日期：1987.6

  rotamer forms. The data reveal an interesting dynamic exchange phenomenon occurring in 1 between two intramolecularly hydrogen bonded conformers. The 1H and 13C chemical shifts, 1H,1H and 13C,1H coupling constants are reported. The 13C and 1H chemical shifts are correlated with the electron densities calculated by the CNDO method.

  通过 1H 和 13C NMR 方法研究三种 1,3-二吡啶基硫脲，即 1,3-二(2-吡啶基)硫脲 (1)、1,3-二(3-吡啶基)硫脲 (2) , 1-(2-吡啶基)-3-(3-吡啶基)硫脲 (3), 以及 1-苯基-3-(2-吡啶基)硫脲 (4) 和 1,3-二苯基硫脲 (5), 包括为了比较，进行了。获得的证据表明 3 和 4 仅以一种形式存在于溶液中，内部氢键 E、Z 构象，而 1、2 和 5 以两种（或更多）旋转异构体形式存在。数据揭示了一种有趣的动态交换现象，发生在两个分子内氢键构象异构体之间的 1 中。报告了 1H 和 13C 化学位移、1H,1H 和 13C,1H 偶联常数。13C 和 1H 化学位移与通过 CNDO 方法计算的电子密度相关。
• On The Synthesis of Pyridinylthiobarbituric Acids
  作者：L. W. Deady、D. Ganame、N. H. Quazi、S. D. Zanatta

  DOI：10.1071/ch02050

  日期：——

  The reaction of N-(pyridin-3-yl) and -4-yl thiourea derivatives with malonyl dichloride in trifluoroacetic acid is shown to be an efficient synthesis of the corresponding thiobarbituric acids. The pyridin-2-yl analogue cleaved and produced, instead, 2-hydroxy-4H-pyrido[1,2a]pyrimidin-4-one.

  N-(pyridin-3-yl) 和 -4-yl 硫脲衍生物与丙二酰二氯在三氟乙酸中的反应被证明是相应硫代巴比妥酸的有效合成。pyridin-2-yl 类似物裂解并产生了 2-hydroxy-4H-pyrido[1,2a]pyrimidin-4-one。
• Synthesis of Thioureas, Thioamides, and Aza-Heterocycles via Dimethyl-Sulfoxide-Promoted Oxidative Condensation of Sulfur, Malonic Acids, and Amines
  作者：Trung Hieu Do、Supasorn Phaenok、Darunee Soorukram、Tina Modjinou、Daniel Grande、Thi Thanh Tam Nguyen、Thanh Binh Nguyen

  DOI：10.1021/acs.orglett.3c02247

  日期：2023.9.1

  Malonic acid and derivatives have been well-known to undergo monodecarboxylation under relatively mild conditions and have been exclusively used as a C2 synthon. We report herein their new application as a C1 synthon via double decarboxylation promoted by sulfur and dimethyl sulfoxide. In the presence of amines as nucleophiles, a wide range of thioureas and thioamides as well as N-heterocycles were

  众所周知，丙二酸及其衍生物在相对温和的条件下进行单脱羧，并专门用作C 2合成子。我们在此报道了它们作为 C 1合成子的新应用，通过硫和二甲亚砜促进的双脱羧作用。在胺作为亲核试剂存在的情况下，在温和的加热条件下，可以以良好至优异的产率获得各种硫脲和硫代酰胺以及N-杂环。