1-(thiocyanatomethyl)naphthalene | 18542-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(thiocyanatomethyl)naphthalene
• 英文别名: 1-naphthylmethyl thiocyanate；Naphthylmethylthiocyanate；naphthalen-1-ylmethyl thiocyanate
• CAS: 18542-48-8
• 化学式: C₁₂H₉NS
• 分子量: 199.276
• InChiKey: MZOWRHBFWYFSLL-UHFFFAOYSA-N

物化性质

• 熔点：
  91-91.5 °C(Solv: methanol (67-56-1))
• 沸点：
  81 °C(Press: 0.2 Torr)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(thiocyanatomethyl)naphthalene 在 TrBF₄ 、 氨 、 sodium 、 一氯化碘 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.17h， 生成 1H-3-iodo-4-(1-naphthylmethylthio)naphtho[1,2-c]thiopyrylium tetrafluoroborate
  参考文献：
  名称：

  Versatile Route to Functionalized 1H-2-Benzothiopyrans and 1H-2-Naphthothiopyrans by Electrophilic Cyclization of Bis(arylmethylthio)acetylenes:  2-Benzo- and 2-Naphthothiopyrylium Salts

  摘要：

  Substituted 1H-2-benzothiopyrans find applications as pharmaceutically active compounds or synthons for more complex sulfur heterocycles. However, restricted variability in their synthesis limits the application for research or industrial purposes. To develop a direct and fast route to substituted and functionalized 1H-2-benzothiopyrans, we investigated the ring closure of symmetrical bis(arylmethylthio)acetylenes with iodine monochloride or bromine. This facile reaction yielded 1H-3-halo-4-arylmethylthio-2-benzo- and 2-naphthothiopyrans via postulated vinyl cations in yields of 47-86%. Substituted 2-benzo- and 2-naphthothiopyrylium salts were prepared by hydride abstraction with triphenylcarbenium tetrafluoroborate from the products, further enhancing the synthetic potential of the found cyclization reaction.

  DOI：

  10.1021/jo972334l
• 作为产物：
  描述：

  甲基萘 在 ammonium cerium(IV) nitrate 作用下， 以 二甲基亚砜 为溶剂， 生成 1-(thiocyanatomethyl)naphthalene
  参考文献：
  名称：

  Cort, Antonella Dalla; Mandolini, Luigi, Gazzetta Chimica Italiana, 1984, vol. 114, # 5/6, p. 283 - 284

  摘要：

  DOI：

文献信息

• AIBN-initiated direct thiocyanation of benzylic sp³ C–H with <i>N</i>-thiocyanatosaccharin
  作者：Di Wu、Yongjie Duan、Kun Liang、Hongquan Yin、Fu-Xue Chen

  DOI：10.1039/d1cc04302a

  日期：——

  Direct thiocyanations of benzylic compounds have been implemented. Here, a new strategy, involving a free radical reaction pathway initiated by AIBN, was used to construct the benzylic sp3 C–SCN bond. In this way, the disadvantage of other strategies involving introducing leaving groups in advance to synthesize benzyl thiocyanate compounds was overcome. The currently developed protocol also involved

  已经实施了苄类化合物的直接硫氰化。在这里，涉及由 AIBN 引发的自由基反应途径的新策略用于构建苄型 sp 3 C-SCN 键。通过这种方式，克服了其他涉及提前引入离去基团以合成硫氰酸苄酯化合物的策略的缺点。目前开发的协议还涉及使用现成的原材料，并导致高产率（高达 100%），这两者都是合成硫氰酸苄酯的巨大优势。
• Sulfuryl Fluoride Promoted Thiocyanation of Alcohols: A Practical Method for Preparing Thiocyanates
  作者：Chengrong Ding、Guofu Zhang、Lidi Xuan、Yiyong Zhao

  DOI：10.1055/s-0040-1707151

  日期：2020.9

  one-step synthesis of thiocyanates through C–O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative

  开发了一种新的 SO2F2 促进的硫氰化方法，通过以硫氰酸铵为硫氰化剂的容易获得的醇的 C-O 键裂解，一步合成硫氰酸盐。该方法避免使用额外的催化剂，并且各种（杂）芳烃、烯烃和脂肪醇在温和条件下在乙酸乙酯中高效反应，以优异的定量收率提供相应的硫氰酸酯，并具有广泛的官能团兼容性。
• Cyclic ammonium salts of dithiocarbamic acid: stable alternative reagents for the synthesis of <i>S</i>-alkyl carbodithioates from organyl thiocyanates in water
  作者：Kinkar Biswas、Sujit Ghosh、Pranab Ghosh、Basudeb Basu

  DOI：10.1080/17415993.2016.1166225

  日期：2016.7.3

  conditions. Here, we report an efficient and practical method for the preparation of libraries of carbodithioate esters from organyl thiocyanates by reacting with cyclic amine-based dithiocarbamic acid salts in water. The protocol is found to be applicable in general to various thiocyanates such as benzyl/aroyl methyl/cinnamyl and so on. Other notable features include no by-products such as disulfides, metal-

  摘要 碳二硫代酸酯是重要的功能性有机硫化合物，广泛应用于制药、农用化学品和材料科学等多个领域。常见的制备方法包括烷基卤化物、二硫化碳和碱在无金属和金属催化条件下的反应。然而，有机硫氰酸酯以前没有被探索过，可能是因为它们在碱性条件下转化为有机二硫化物。在这里，我们报告了一种通过与基于环胺的二硫代氨基甲酸盐在水中反应，从有机硫氰酸酯制备碳二硫代酯库的有效且实用的方法。发现该方案通常适用于各种硫氰酸酯，例如苄基/芳酰基甲基/肉桂基等。其他显着特点包括无二硫化物等副产品，无金属和无碱的水性条件，最终容易且近乎定量地形成环胺基二硫代氨基甲酸盐作为稳定的替代试剂。图形概要
• A novel base-induced cyclization of selected benzyl alkynyl sulfides for the synthesis of 2-aryl-2,3-dihydrothiophenes
  作者：Laura K McConachie、Adrian L Schwan

  DOI：10.1016/s0040-4039(00)00916-3

  日期：2000.7

  2-Halobenzyl 1-alkynyl sulfides undergo an unprecedented dihydrothiophene formation when treated with 2 equiv. of KOtBu in CH3CN. The reaction, believed to proceed via a 5-endo-dig cyclization, is sluggish or non-existent in the absence of the halogen.

  当用2当量处理时，2-卤代苄基1-炔基硫化物经历前所未有的二氢噻吩形成。CH 3 CN中KO t Bu的摩尔数。据信该反应是通过5-内挖-环化进行的，在没有卤素的情况下反应缓慢或不存在。
• An ionic liquid supported on magnetite nanoparticles as an efficient heterogeneous catalyst for the synthesis of alkyl thiocyanates in water
  作者：Mehdi Fallah-Mehrjardi、Soheil Sayyahi

  DOI：10.1080/17415993.2021.1885673

  日期：2021.5.4

  The present study describes a convenient method to synthesize alkyl thiocyanates from alkyl halides with the use of a novel nanomagnetic-supported organocatalyst (MNP@PEG-ImCl). The new supported ionic liquid is fully characterized by field-emission scanning electron microscopy (FESEM), Fourier-transform infrared (FT-IR), energy dispersive X-ray analysis (EDAX), X-ray powder diffraction (XRD), transmission

  摘要 本研究描述了一种方便的方法，可以使用新型纳米磁性负载的有机催化剂（MNP @ PEG-ImCl）从烷基卤化物合成烷基硫氰酸酯。新型负载型离子液体具有场发射扫描电子显微镜（FESEM），傅立叶变换红外（FT-IR），能量色散X射线分析（EDAX），X射线粉末衍射（XRD）和透射电子的完整特征显微镜（TEM），振动样品磁力法（VSM）以及热重分析（TGA）技术。值得注意的是，我们观察到通过简单的磁倾析法很容易将催化剂从反应混合物中分离出来，并多次重复利用而没有任何明显的活性损失。