1,3-二(萘-2-基)硫脲 | 1166-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,3-二(萘-2-基)硫脲
• 英文名称: N,N'-di(2-naphthyl)thiourea
• 英文别名: 1,3-di-naphthalen-2-yl-thiourea；N,N'-di-[2]naphthyl-thiourea；N,N'-Di-[2]naphthyl-thioharnstoff；N.N'-Di-β-naphthyl-thioharnstoff；N,N'-di-2-naphthalenyl-thiourea；N,N'--thioharnstoff；1,3-Dinaphthalen-2-ylthiourea
• CAS: 1166-32-1
• 化学式: C₂₁H₁₆N₂S
• 分子量: 328.437
• InChiKey: YXGYUUQULAOVTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-二(萘-2-基)硫脲 在 铁粉 、 paraffin oil 作用下， 生成 2-萘甲腈
  参考文献：
  名称：

  DE259363

  摘要：

  公开号：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 作用下， 生成 1,3-二(萘-2-基)硫脲
  参考文献：
  名称：

  Heller; Bauer, Journal fur praktische Chemie (Leipzig 1954), 1902, vol. <2>65, p. 378

  摘要：

  DOI：

文献信息

• An Environmentally Benign Method for the Synthesis of Symmetrical<i>N, N</i>′-Disubstituted Thioureas in a Water Medium
  作者：Zheng Li、Zhi-Yuan Wang、Yan-Long Zhao、Yu-Lin Xing、Wei Zhu

  DOI：10.1080/104265090968082

  日期：2005.12

  An environmentally benign method for the synthesis of symmetrical N, N′-disubstituted thioureas in a water medium using poly(ethylene glycol)-400 (PEG-400) as a catalyst and a microwave as a heating source is described. Diaryl- and dialkyl-thioureas efficiently are synthesized by the reactions of thiourea with a variety of amines. This protocol has advantages of (a) no use of hazardous reagents and

  描述了一种在水介质中使用聚 (乙二醇)-400 (PEG-400) 作为催化剂和微波作为加热源合成对称 N, N'-二取代硫脲的环境友好方法。二芳基硫脲和二烷基硫脲通过硫脲与多种胺的反应有效合成。该协议的优点是 (a) 不使用危险试剂和挥发性有机溶剂, (b) 反应速度快, (c) 产量高, (d) 后处理程序简单。
• Catalytic properties of rhenium(v) complexes with thiourea derivatives in cyclohexene hydrogenation
  作者：M. A. Ryashentseva、L. V. Borisova

  DOI：10.1007/bf02496343

  日期：2000.10

  The catalytic properties of ReVOL2Cl3 complexes, where L are thiourea derivatives, were studied. The rhenium(v) complex with di-o-tolylthiourea is most active in cyclohexene hydrogenation

  研究了 ReVOL2Cl3 配合物的催化性能，其中 L 是硫脲衍生物。铼（v）与二邻甲苯基硫脲的配合物在环己烯加氢反应中最活跃
• 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。
• Sulfur‐ and Amine‐ Promoted Multielectron Autoredox Transformation of Nitromethane: Multicomponent Access to Thiourea Derivatives
  作者：Supasorn Phaenok、Le Anh Nguyen、Darunee Soorukram、Thi Thanh Tam Nguyen、Pascal Retailleau、Thanh Binh Nguyen

  DOI：10.1002/chem.202303703

  日期：2024.2

  Thiourea derivatives are in‐demand motifs in organic synthesis, medicinal chemistry and material science, yet redox methods for the synthesis that start from safe, simple, inexpensive and readily available feedstocks are scarce. In this article, we disclose the synthesis of these motifs using elemental sulfur and nitromethane as the starting materials. The method harnesses the multi‐electron auto‐redox property of nitromethane in the presence of sulfur and amines, delivering thiourea products without any added oxidant or reductant. Extension of this reaction to cyclizable amines and/or higher homologues of nitromethane led to a wide range of nitrogen heterocycles and thioamides. Operationally simple, the reactions are scalable, tolerate a wide range of functional groups, and can be employed for the direct functionalization of natural products. Mechanistically, the nitro group was found to act as an oxidant leaving group, being reduced to ammonia whereas sulfur, along with the role of a sulfur building block for the thiocarbonyl group, behaved as a complementary reductant, being oxidized to sulfate.

  摘要 硫脲衍生物是有机合成、药物化学和材料科学中炙手可热的基团，然而以安全、简单、廉价和易于获得的原料为起始原料的氧化还原合成方法却十分稀缺。本文披露了以元素硫和硝基甲烷为起始原料合成这些基团的方法。该方法利用了硝基甲烷在硫和胺存在下的多电子自动氧化还原特性，在不添加任何氧化剂或还原剂的情况下生成硫脲产品。将这一反应扩展到可环化胺和/或硝基甲烷的更高同系物，可得到多种氮杂环和硫代酰胺。该反应操作简单，可扩展性强，可容忍多种官能团，可用于天然产物的直接官能化。从机理上讲，硝基可作为氧化剂离去基团，被还原成氨，而硫作为硫代羰基的硫构件，可作为互补还原剂，被氧化成硫酸盐。
• Dash,B.C.; Mahapatra,G.N., Journal of the Indian Chemical Society, 1967, vol. 44, p. 939 - 942
  作者：Dash,B.C.、Mahapatra,G.N.

  DOI：——

  日期：——