1-methoxy-3-(thiocyanatomethyl)benzene | 1233513-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-3-(thiocyanatomethyl)benzene
• 英文别名: 3-methoxybenzyl thiocyanate；(3-methoxyphenyl)methyl thiocyanate
• CAS: 1233513-38-6
• 化学式: C₉H₉NOS
• mdl: MFCD09025704
• 分子量: 179.243
• InChiKey: BAWQGDICORFTBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险类别：
  9
• 危险性防范说明：
  P501,P261,P273,P272,P270,P271,P264,P280,P284,P302+P352,P391,P342+P311,P337+P313,P305+P351+P338,P362+P364,P333+P313,P301+P312+P330,P304+P340+P312
• 危险品运输编号：
  3082
• 危险性描述：
  H302+H332,H315,H319,H317,H334,H400
• 包装等级：
  III

反应信息

• 作为产物：
  描述：

  3-甲氧基苯乙酸 、 N-thiocyanatosaccharin 在 2,4,6-triphenylpyrylium tetrafluoroborate 、 sodium carbonate 作用下， 以 氯苯 为溶剂， 以65 %的产率得到1-methoxy-3-(thiocyanatomethyl)benzene
  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

• Thiocyanation and 2-Amino-1,3-thiazole Formation in Water Using Recoverable and Reusable Glycosylated Resorcin[4]arene Cavitands
  作者：Ali A. Husain、Kirpal S. Bisht

  DOI：10.1021/acs.joc.0c01150

  日期：2020.8.7

  resorcin[4]arene cavitand glycoconjugates (RCGs) have been applied as efficient recoverable and reusable inverse phase transfer catalysts for eco- and environmentally friendly thiocyanation and 2-amino-1,3-thiazole formation reactions in water. The results show that RCGs (1 mol %) were capable of hosting and catalyzing various water-insoluble bromo/thiocyanato substrates in water without the use of any co-organic

  三种空间定向间苯二酚[4]芳烃cavitand糖共轭物（RCGs）系列已被用作高效可回收和可重复使用的反相转移催化剂，用于生态和环境友好的硫氰化和2-氨基-1,3-噻唑在水中的形成反应。结果表明，在不使用任何共有机溶剂的情况下，RCG（1摩尔％）能够在水中容纳和催化各种水不溶性溴/硫氰酸根基质。在使用DCM或乙酸乙酯对所需产物进行简单萃取后，再对回收的含有HCG催化剂的水溶液进行处理，还检查了RCG催化体系RCG1和RCG3的可回收性和可重复使用性。RCG催化剂进入下一个反应周期。
• Antimicrobial volatile glucosinolate autolysis products from Hornungia petraea (L.) Rchb. (Brassicaceae)
  作者：Niko S. Radulović、Milan S. Dekić、Zorica Z. Stojanović-Radić

  DOI：10.1016/j.phytol.2012.02.017

  日期：2012.6

  isothiocyanate, along with several other structurally related compounds were evaluated for antimicrobial activity in order to possibly pinpoint the role of the latter secondary metabolites in the plant tissues. The assays showed a very high antibacterial activity of the tested isothiocyanates against Sarcina lutea and an antifungal effect against Aspergillus fumigatus and Candida albicans with MIC values

  首次对Hornungia petraea的植物样品中的芥子油苷（GLS）自溶代谢产物进行了分析。GC-MS对自溶物的分析和一系列可能的芥子油苷分解产物的合成（12种化合物）表明/证实了该物种中最有可能的“芥子油”前体中存在葡糖金葡菌素，葡糖基甜菜碱，葡糖菊糖苷和葡糖过氧化物酶。GLS降解产物的自溶鉴定H.佩特拉行省评估了异硫氰酸苄酯，3-和4-甲氧基异硫氰酸苄酯以及其他几种与结构相关的化合物的抗菌活性，以便可能查明后者次生代谢产物在植物组织中的作用。该测定显示了测试的异硫氰酸酯对褐藻的极高的抗菌活性以及对烟曲霉和白色念珠菌的抗真菌作用，其MIC值约为1μg/ ml。
• Crown ether functionalized magnetic hydroxyapatite as eco‐friendly microvessel inorganic‐organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives
  作者：Maedeh Azaroon、Ali Reza Kiasat

  DOI：10.1002/aoc.4046

  日期：2018.2

  (γ‐Fe2O3@HAp–Crown) as a new, versatile and magnetically recoverable catalyst, was prepared. It evaluated as phase‐transfer catalyst and molecular host system for nucleophilic substitution reactions of benzyl halides with thiocyanate, cyanide, azide and acetate anions in water. No evidence for the formation of by‐products was observed and the products obtained in pure form without further purification. The

  在本文中，4个催化活性高'，4“-diformyl二苯并-18-冠-6锚定在官能磁铁矿羟基磷灰石（γ-的Fe 2 ö 3制备了一种新的，多用途且可磁回收的催化剂@@ HAp-Crown。它被用作相转移催化剂和分子主体系统，用于水中卤化苄基卤与硫氰酸根，氰化物，叠氮化物和乙酸根阴离子的亲核取代反应。没有观察到形成副产物的证据，并且没有进一步纯化就以纯净形式获得了产物。通过施加磁场，可以轻松地从溶液中去除纳米复合材料，从而实现直接回收和再利用。合成的纳米复合材料通过多种技术进行了表征，如FT-IR，TGA-DTG，EDX，XRD，BET，FE-SEM，TEM和VSM。
• β-Cyclodextrin conjugated magnetic nanoparticles as a novel magnetic microvessel and phase transfer catalyst: synthesis and applications in nucleophilic substitution reaction of benzyl halides
  作者：Ali Reza Kiasat、Simin Nazari

  DOI：10.1007/s10847-012-0207-8

  日期：2013.8

  This paper presents a feasible protocol for the preparation of β-cyclodextrin conjugated Fe3O4 magnetic nanoparticles as an efficient microvessel and host system for nucleophilic substitution reaction of benzyl halides in water. No evidence for the formation of by-product for example isothiocyanate or benzyl alcohol was observed and the products were obtained in pure form without further purification

  本文提出了一种制备 β-环糊精共轭 Fe3O4 磁性纳米粒子的可行方案, 作为一种有效的微血管和宿主系统, 用于苄基卤化物在水中的亲核取代反应。没有观察到形成副产物例如异硫氰酸酯或苯甲醇的证据，并且产物以纯形式获得而无需进一步纯化。FT-IR、XRD、TGA 和SEM 的特征结果表明β-CD 接枝到 纳米颗粒上。通过使用外部磁铁，纳米磁性催化剂可以很容易地从溶液中分离出来，从而可以直接回收和再利用。
• Magnetic nanoparticles grafted with β-cyclodextrin–polyurethane polymer as a novel nanomagnetic polymer brush catalyst for nucleophilic substitution reactions of benzyl halides in water
  作者：Ali Reza Kiasat、Simin Nazari

  DOI：10.1016/j.molcata.2012.08.012

  日期：2012.12

  The polymer coated magnetic nanoparticles has gained significant attention for potential applications in biomedicine, separations, and magnetic storage. In this study, beta-cyclodextrin-polyurethane polymer coated Fe3O4 magnetic nanoparticle as a novel class of hybrid organic/inorganic molecular catalyst was successfully prepared and evaluated as solid-liquid phase-transfer catalyst and molecular host system for nucleophilic substitution reactions. The nanocomposite has demonstrated the ability to catalytic the nucleophilic substitution reaction of benzyl halides with thiocyanate, azide, cyanide and acetate anions in water. No evidence for the formation of by-products for example isothiocyanate or alcohol was observed and the products obtained in pure form without further purification. The nanomagnetic polymer brush catalyst was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. Results obtained from scanning electron microscopy (SEM) and vibrating sample magnetometery (VSM) show that the synthesized magnetic nanocomposite are superparamagnetic with a mean diameter of 59 nm. The grafting of beta-cyclodextrin-polyurethane polymer to Fe3O4 magnetic nanoparticle is confirmed by Fourier transform infrared spectroscopy (FT-IR). (C) 2012 Elsevier B.V. All rights reserved.