4-(thiocyanatomethyl)-1,1'-biphenyl | 112028-25-8

• 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-(thiocyanatomethyl)-1,1'-biphenyl
• 英文别名: (4-Phenylphenyl)methyl thiocyanate
• CAS: 112028-25-8
• 化学式: C₁₄H₁₁NS
• 分子量: 225.314
• InChiKey: SSQVEIQPAWPONK-UHFFFAOYSA-N

物化性质

• 沸点：
  387.5±21.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-联苯乙酸 、 N-thiocyanatosaccharin 在 2,4,6-triphenylpyrylium tetrafluoroborate 、 sodium carbonate 作用下， 以 氯苯 为溶剂， 以59 %的产率得到4-(thiocyanatomethyl)-1,1'-biphenyl
  参考文献：
  名称：

  可见光促进羧酸催化脱羧硫氰化和异硫氰化的发散过程

  摘要：

  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。

  DOI：

  10.1039/d3cc04624a

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。
• Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide
  作者：Mohammad Ali Karimi Zarchi、Asmaosadat Tabatabaei Bafghi

  DOI：10.1080/17415993.2015.1035273

  日期：2015.7.4

  convenient procedure for one-pot conversion of alcohols into the corresponding alkyl thiocyanates in the presence of cross-linked poly (N-propyl-4-vinylpyridinium) thiocyanate ion [P4-VP]Pr-SCN, promoted by cyanuric chloride/dimethylformamide, is described. Various alcohols were converted to their corresponding alkyl thiocyanates and it was observed that substituted benzyl alcohol with electron-withdrawing

  在氰尿酰氯/二甲基甲酰胺的促进下，在交联聚（N-丙基-4-乙烯基吡啶鎓）硫氰酸根离子[P4-VP]Pr-SCN存在下，将醇一锅法转化为相应的烷基硫氰酸盐的简便方法，被描述。将各种醇转化为其相应的硫氰酸烷基酯，观察到具有吸电子或给电子基团的取代苯甲醇在短时间内以高产率转化为相应的硫氰酸苄酯衍生物，但产生了空间位阻醇相应的硫氰酸盐收率很低。
• Photoinduced Synthesis of Thiocyanates through Hydrogen Atom Transfer and One-Pot Derivatization to Isothiocyanates
  作者：Bumpei Maeda、Yusuke Aihara、Ayato Sato、Toshinori Kinoshita、Kei Murakami

  DOI：10.1021/acs.orglett.2c02896

  日期：2022.10.14

  Photoinduced benzylic C–H thiocyanation is described. A series of alkyl thiocyanates were efficiently obtained by using Selectfluor as the oxidant. Moreover, we accomplished the one-pot isothiocyanation following the C–H thiocyanation. The thiocyanates and isothiocyanates were applied to the divergent transformation of pharmaceuticals.

  描述了光诱导的苄基 C-H 硫氰化。以Selectfluor为氧化剂，高效制得了一系列硫氰酸烷基酯。此外，我们完成了 C-H 硫氰化后的一锅异硫氰化。硫氰酸盐和异硫氰酸盐被应用于药物的发散转化。
• Decarboxylative cyanation and thiocyanation via catalytic electron donor-acceptor complex with copper catalysis
  作者：Hongping Zhao、Xiaoxiang Xi、Tianbao Wu、Zimin Chen、Minyan Wang、Weiming Yuan

  DOI：10.1007/s11426-024-2123-0

  日期：2024.9

  secondary, and tertiary alkyl nitriles and thiocyanates are easily synthesized. Moreover, an asymmetric decarboxylative cyanation by applying a chiral Cu catalyst is also developed to afford chiral nitriles in high enantioselectivity. The mechanistic details and the origin of the high enantioselectivity are further investigated by the mechanistic experiments and the density functional theory calculations.

  开发了一种通过协同 NaI/Cu 催化进行的新型催化脱羧氰化和硫氰化。由NaI、R 3 P和N-酰氧基邻苯二甲酰亚胺酯（NHPI酯）组装而成的光激发电子供体-受体复合物引发烷基自由基物质的产生，然后参与Cu催化的自由基偶联过程。这种双重催化转化成功的关键是 I· 和 Cu(I) 之间可靠的电荷转移。这种双催化平台可以消除昂贵的铱基光催化剂或人工合成的有机染料的使用。一系列伯、仲、叔烷基腈和硫氰酸盐很容易合成。此外，还开发了通过应用手性铜催化剂的不对称脱羧氰化，以提供高对映选择性的手性腈。通过机理实验和密度泛函理论计算进一步研究了高对映选择性的机理细节和起源。
• Selectfluor™ F-TEDA-BF4 mediated thiocyanation or isothiocyanation of alcohols by in situ generation of [+SCN] under heterogeneous and neutral conditions
  作者：Ardeshir Khazaei、Sadegh Rahmati、Ali Khalafi-nezhad、Shahnaz Saednia

  DOI：10.1016/j.jfluchem.2012.03.005

  日期：2012.5

  A convenient approach for thiocyanation of alcohols has been developed using ammonium thiocyanate as thiocyanating agent in the presence of a catalytic amount of Selectfluor (TM) F-TEDA-BF4 in aqueous acetonitrile. In this method various alcohols generally afforded the corresponding thiocyanates or isothiocyanates directly in good to high yield under heterogeneous and neutral conditions. (c) 2012 Elsevier B.V. All rights reserved.