4-cyanobenzyl thiocyanate | 112028-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-cyanobenzyl thiocyanate
• 英文别名: (4-cyanophenyl)methyl thiocyanate
• CAS: 112028-28-1
• 化学式: C₉H₆N₂S
• 分子量: 174.226
• InChiKey: GCCJAUYAIJAPFG-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-cyanobenzyl thiocyanate 在 盐酸 作用下， 生成 4,4'-bis(thiomethylene)dibenzoic acid
  参考文献：
  名称：

  Moses, Chemische Berichte, 1900, vol. 33, p. 2626

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium thioacyanate 、 对氰基氯苄 在 乙醇 作用下， 生成 4-cyanobenzyl thiocyanate
  参考文献：
  名称：

  Moses, Chemische Berichte, 1900, vol. 33, p. 2626

  摘要：

  DOI：

文献信息

• 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。
• Substitution Reaction of Organic Halide by Trimethylsilyl Isothiocyanate: Formation of Thiocyanate and Its Rearrangement to Isothiocyanate
  作者：Kozaburo Nishiyama、Makoto Oba

  DOI：10.1246/bcsj.60.2692

  日期：1987.7

  The reaction of organic halide with trimethylsilyl isothiocyanate (TMSTC) gave thiocyanate 1 and its isomerized isothiocyanate 2. Details of the substituion and the isomerization reactions were examined.

  有机卤化物与异硫氰酸三甲基甲硅烷基酯 (TMSTC) 的反应得到硫氰酸酯 1 及其异构化的异硫氰酸酯 2。对取代和异构化反应的细节进行了检查。
• Electron-transfer induced rearrangement of thiocyanate to isothiocyanate
  作者：Kan Wakamatsu、Jun Dairiki、Tetsuo Etoh、Hiroshi Yamamoto、Satoshi Yamamoto、Yasumasa Shigetomi

  DOI：10.1016/s0040-4039(99)02063-8

  日期：2000.1

  Benzyl thiocyanates with an electron-withdrawing group (1a, 1b) and 9-fluorenyl thiocyanate (1e) rearrange to the corresponding isothiocyanate (2) under 9,10-diphenylanthracene (DPA) sensitization. The rearrangement would proceed via carbon–sulfur bond cleavage in an anion radical of 1 produced by photoinduced electron transfer, followed by back electron transfer to DPA·+ and recombination of the resulting

  在9,10-二苯基蒽（DPA）敏化作用下，具有吸电子基团（1a，1b）和9-芴基硫氰酸酯（1e）的硫氰酸苄酯重排为相应的异硫氰酸酯（2）。重排将通过光诱导的电子转移产生的阴离子基团1中的碳硫键断裂而进行，然后将电子反向转移至DPA ·+并重组所得的基团或离子对。
• Divergent process for the catalytic decarboxylative thiocyanation and isothiocyanation of carboxylic acids promoted by visible light
  作者：Jordan Vigier、Mélissa Gao、Philippe Jubault、Hélène Lebel、Tatiana Besset

  DOI：10.1039/d3cc04624a

  日期：——

  A divergent photoinduced selective synthesis of thiocyanate and isothiocyanate derivatives from readily available carboxylic acids was developed using N-thiocyanatosaccharin and a catalytic amount of base or acid. This molecular editing strategy allowed the functionalization of bioactive compounds. A mechanism for the transformation was proposed based on control experiments.

  使用N-硫氰酸糖精和催化量的碱或酸，开发了从容易获得的羧酸中发散光诱导选择性合成硫氰酸酯和异硫氰酸酯衍生物的方法。这种分子编辑策略允许生物活性化合物的功能化。基于控制实验提出了一种转化机制。
• A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate
  作者：H.M. Meshram、Pramod B. Thakur、B. Madhu Babu、Vikas M. Bangade

  DOI：10.1016/j.tetlet.2012.01.113

  日期：2012.4

  A very rapid, convenient, and general method for the synthesis of alpha-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl alpha-halo carbonyls, beta-keto tosylates, alpha-halo beta-dicarbonyl, alpha-tosyl, beta-dicarbonyl, alkyl halide, and alkyl tosylates. (C) 2012 Elsevier Ltd. All rights reserved.