1-butyl-3-(naphthalen-1-yl)thiourea | 25160-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-butyl-3-(naphthalen-1-yl)thiourea
• 英文别名: N-butyl-N'-[1]naphthyl-thiourea；N-Butyl-N'-[1]naphthyl-thioharnstoff；N-butyl-N'-1-naphthalenyl-thiourea；N-Butyl-N'-(1-naphthyl)-thioharnstoff；1-Butyl-3-naphthalen-1-ylthiourea
• CAS: 25160-69-4
• 化学式: C₁₅H₁₈N₂S
• 分子量: 258.387
• InChiKey: CUZUJJHZAFWOCD-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  394.4±25.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-butyl-3-(naphthalen-1-yl)thiourea 、 甲酰肼 在 碘 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以62%的产率得到4-butyl-N-(naphthalene-1yl)-4H-1,2,4-triazol-3-amine
  参考文献：
  名称：

  Tandem synthesis of [1,2,4]-triazoles mediated by iodine—a regioselective approach

  摘要：

  A tandem regioselective one-pot synthesis of 3-amino-[1,2,4]-triazoles has been achieved from 1,3-disubstituted thioureas using molecular iodine. In this one-pot strategy, the intermediate carbodiimide generated in situ from thiourea upon reaction with HCONHNH2 gives diaryl/alkylhydrazinecarboximidamide or acylureidrazone, which then undergoes an intramolecular cyclodehydration to afford the corresponding 3-amino-[1,2,4]-triazole. The product regioselectivity for unsymmetrical 1,3-disubstituted thioureas correlate well with the pK(a)s of the parent amines attached, in which the amine having higher pK(a) goes to the ring nitrogen while the other nitrogen remains flanked as an exocyclic nitrogen of the triazole core. This method is milder and environmentally sustainable giving good to excellent yields of the desired products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.042
• 作为产物：
  描述：

  正丁胺 、 1-萘异硫氰酸酯 以 氯仿 为溶剂， 反应 15.0h， 以87%的产率得到1-butyl-3-(naphthalen-1-yl)thiourea
  参考文献：
  名称：

  A reversible Em-FRET rhodamine-based chemosensor for carboxylate anions using a ditopic receptor strategy

  摘要：

  利用二位受体策略设计并合成了一种能够进行准分子荧光共振能量转移（Em-FRET）的可逆罗丹明传感器（L1）。在 L1 的溶液中加入 Cu2+ 离子会诱导螺内酰胺形成开环构象（Em-FRET 开），而加入 CH3COO- 则会诱导闭环（Em-FRET 关）。

  DOI：

  10.1039/b9nj00594c

文献信息

• Synthesis and anion recognition properties of 8,8′-dithioureido-2,2′-binaphthalene
  作者：Shin-ichi Kondo、Masanori Nagamine、Yumihiko Yano

  DOI：10.1016/j.tetlet.2003.09.207

  日期：2003.12

  A novel artificial receptor based on 2,2′-binaphthalene skeleton bearing two thiourea groups was prepared via nickel(II)-catalyzed homocoupling of the corresponding bromide. The receptor showed high binding ability for F− and AcO− in acetonitrile.

  通过镍（II）催化相应的溴化物的均偶联反应，制备了基于带有2个硫脲基的2,2'-双萘骨架的新型人工受体。受体表现出对F高结合能力-与ACO -乙腈。
• Dyson; Hunter; Soyka, Journal of the Chemical Society, 1926, p. 2966
  作者：Dyson、Hunter、Soyka

  DOI：——

  日期：——
• Anion recognition by 2,2′-binaphthalene derivatives bearing urea and thiourea groups at 8- and 8′-positions by UV–vis and fluorescence spectroscopies
  作者：Shin-ichi Kondo、Masanori Nagamine、Satoshi Karasawa、Masaya Ishihara、Masafumi Unno、Yumihiko Yano

  DOI：10.1016/j.tet.2010.12.004

  日期：2011.2

  Synthesis and anion recognition properties of 2,2'-binaphthalene derivatives bearing two thiourea (1) and urea (2) groups at 8- and 8'-positions were studied. The structure of receptor 1 was determined by Xray crystallography. UV-vis spectra of the receptors showed characteristic changes around 300-400 nm through isosbestic points upon the addition of biologically relevant anions such as acetate, dihydrogenphosphate, and chloride in MeCN and DMSO due to restriction of the rotation around the single bond connecting two naphthyl moieties by cooperative guest binding of two recognition sites. Job's plots showed 1:1 complexation for guest anions. The fluorescence quantum yields of free form of 1 and 2 in MeCN were determined to be 0.021 and 0.57, respectively. The fluorescence intensities of the receptors diminished upon the addition of anions in MeCN. The association constants of receptors 1 and 2 were one or two orders of magnitude greater than the corresponding monothiourea and urea receptors 3 and 4 indicating cooperative hydrogen bonding with guest anions. The selectivity trends of association of anions were F->AcO->H2PO4->Cl->>HSO4- approximate to NO3- approximate to Br- approximate to l(-) for 1, and F->AcO- approximate to Cl->H2PO4-> Br->HSO4->l(-) approximate to NO3- for 2. Receptor 2 showed remarkable Cl- selectivity presumably owing to suitable orientation for effective hydrogen bond formation with Cl-. (C) 2010 Elsevier Ltd. All rights reserved.
• Dyson; Hunter; Morris, Journal of the Chemical Society, 1932, p. 2283
  作者：Dyson、Hunter、Morris

  DOI：——

  日期：——
• Alpha-Naphthyl Isothiocyanate as a Reagent for Primary and Secondary Aliphatic Amines
  作者：C. M. Suter、Eugene W. Moffett

  DOI：10.1021/ja01333a042

  日期：1933.6