4-thiocyanatonaphthalen-1-ol | 6186-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-thiocyanatonaphthalen-1-ol
• 英文别名: 4-thiocyanato-1-naphthol；Thiocyansaeure-(4-hydroxy-naphthyl-(1)-ester)；4-Hydroxy-1-thiocyanato-naphthalin；4-Hydroxy-naphthyl-(1)-thiocyanat；4-Thiocyanato-[1]naphthol；(4-Oxy-naphthyl-(1))-rhodanid；4-Hydroxynaphthalen-1-yl thiocyanate；(4-hydroxynaphthalen-1-yl) thiocyanate
• CAS: 6186-86-3
• 化学式: C₁₁H₇NOS
• 分子量: 201.249
• InChiKey: KVFAHZPKQSOLAA-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C
• 沸点：
  417.4±28.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-thiocyanatonaphthalen-1-ol 在 盐酸 、 乙醇 、 双氧水 、 锌 作用下， 生成 二(4-羟基-1-萘基)二硫醚
  参考文献：
  名称：

  Kaufmann; Liepe, Berichte der Deutschen Pharmazeutischen Gesellschaft, vol. 33, p. 148

  摘要：

  DOI：
• 作为产物：
  描述：

  lead(II) thiocyanate 在 四氯化碳 、 磺酰氯 作用下， 生成 4-thiocyanatonaphthalen-1-ol
  参考文献：
  名称：

  DE439604

  摘要：

  公开号：

文献信息

• Compounds that modulate PPAR activity and methods of preparation
  申请人：——

  公开号：US20030207916A1

  公开（公告）日：2003-11-06

  This invention discloses compounds that alter PPAR activity. The invention also discloses pharmaceutically acceptable salts of the compounds, pharmaceutically acceptable compositions comprising the compounds or their salts, and methods of using them as therapeutic agents for treating or preventing hyperlipidemia and hypercholesteremia in a mammal. The present invention also discloses method for making the disclosed compounds.

  这项发明揭示了能够改变PPAR活性的化合物。该发明还揭示了这些化合物的药用盐、包含这些化合物或其盐的药用组合物，以及将它们用作治疗或预防哺乳动物高脂血症和高胆固醇血症的治疗剂的方法。本发明还揭示了制备所述化合物的方法。
• <i>N</i>-Thiocyanato-dibenzenesulfonimide: a new electrophilic thiocyanating reagent with enhanced reactivity
  作者：Chengqiu Li、Pingliang Long、Haopeng Wu、Hongquan Yin、Fu-Xue Chen

  DOI：10.1039/c9ob01340g

  日期：——

  A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2

  制备了一种新型的亲电子硫氰酸化试剂，N-硫氰基-二苯磺酰亚胺，并在广泛的底物范围内表现出增强的亲电子性。因此，它与活化的芳族化合物（如苯酚，吲哚，苯胺和茴香醚）在没有催化剂的情况下以高收率反应生成相应的硫氰酸盐衍生物，而未活化的芳烃和杂芳族化合物的TfOH和酮的Zn（OTf）2被用作催化剂，分别。值得注意的是，内部烯烃和苯乙烯被双官能化，从而以高收率得到1,2-氨基硫氰酸酯。
• Thiocyanation of Aromatic and Heteroaromatic Compounds with 1-Chloro-1,2-benziodoxol-3-(1&lt;i&gt;H&lt;/i&gt;)-one and (Trimethylsilyl)isothiocyanate
  作者：Yuta Ito、Akihiro Touyama、Minako Uku、Hiromichi Egami、Yoshitaka Hamashima

  DOI：10.1248/cpb.c19-00352

  日期：2019.9.1

  Thiocyanation of aromatic compounds has been investigated using the combination of 1-chloro-1,2-benziodoxol-3-(1H)-one (1) and (trimethylsilyl)isothiocyanate (TMSNCS). The reaction with electron rich aromatic compounds proceeded smoothly to provide the thiocyanated products in high yield, while electron deficient heteroaromatic compounds were not suitable for this reaction. In these reactions, the regioselectivity

  已使用1-氯-1,2-苯并恶唑3-（1H）-一（1）和（三甲基甲硅烷基）异硫氰酸酯（TMSNCS）的组合研究了芳族化合物的硫氰酸化。与富电子芳族化合物的反应进行得很顺利，以高收率提供了硫氰酸化产物，而缺电子的杂芳族化合物不适合该反应。在这些反应中，区域选择性通常很高。还研究了产物的转化以证明反应的效用。基于NMR实验，我们建议原位生成氯化硫氰作为活性物质。
• An Efficient p-Thiocyanation of Phenols and Naphthols Using a Reagent Combination of Phenyliodine Dichloride and Lead(II) Thiocyanate.
  作者：Yasuyuki KITA、Yoshifumi TAKEDA、Takayuki OKUNO、Masahiro EGI、Kiyosei IIO、Ken-ichi KAWAGUCHI、Shuji AKAI

  DOI：10.1248/cpb.45.1887

  日期：——

  A combination of PhICl2 and Pb(SCN)2 is effective for the p-selective thiocyanation of various types of p-unsubstituted phenols and naphthols 1 to give p-thiocyanatophenols and naphthols 3. The reaction proceeded at 0°C to room temperature in good to quantitative yields. Twenty-five examples are given, in which various functional groups, such as chloro, allyl, carbonyl, ester, amide, and primary hydroxyl groups, are shown to be compatible with this reaction.

  PhICl2 和 Pb(SCN)2 的组合可有效地对各种类型的对未取代苯酚和萘酚 1 进行对选择性硫氰酸化，从而得到对硫氰酸苯酚和萘酚 3。反应在 0°C 至室温下进行，产率高至定量。文中给出了 25 个例子，表明氯基、烯丙基、羰基、酯基、酰胺基和伯羟基等各种官能团与该反应相容。
• Oxidant-free thiocyanation of phenols and carbonyl compounds under solvent-free conditions by AlCl₃/NH₄SCN
  作者：Kobra Nikoofar、Samareh Gorji

  DOI：10.1080/17415993.2015.1091888

  日期：2016.1.2

  A simple, efficient, solvent-free, and mild method for thiocyanation of phenols by ammonium thiocyanate (NH4SCN) in the presence of AlCl3 has been developed. This new methodology was used to prepare para-thiocyanated products in good to excellent yields at 70 degrees C. In addition, the successful alpha-thiocyanation of various ketones has also been described. Finally, a plausible mechanism of thiocyanation has been suggested.[GRAPHICS]