CAS: 622-78-6; Benzylisothiocyanate

该化合物是一种有机化合物,其分子式为C9H9NCS,其特点是存在一个附于苯基组的异硫氰酸盐功能组(-N=C=S),该化合物一般是一种无色的黄色液体,其颗粒色色色的黄色液体,其颗粒色色色的味色素与芥子的相似性,可溶于乙醇和乙醚等有机溶剂,但在水中溶解性有限.Benzyl异硫酸盐因其生物活动而闻名,表现出抗微生物和抗硫酸盐的特性,因此对食品保存和可能的治疗用途感兴趣.此外,该化合物还被用于各种化学化合物的合成,并作为有机化学的试剂.由于其反应性作用性异硫氰酸盐组,它可以参与核细胞反应,从而在药品和农用化学物的开发过程中具有价值.然而,在处理该化合物时,应谨慎行事,因为它可能会刺激皮肤和呼吸系统.

结构式图片

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合成工艺路线路线简述

  • 合成目标产物 Benzyl Isothiocyanate 主要起始原料 Carbon Disulfide And Benzylamine
  • (文献来源)合成步骤主要原料 Carbon Disulfide 和 Benzylamine
苄异腈置于selenium,Sulfur,三乙胺体系中,用 四氢呋喃 作为反应溶剂,化学反应 1.0H,以81%的收率获得产物异硫氰酸苯甲酯
参考文献:新型硒催化异氰酸酯和元素硫合成异硫氰酸酯
标题:新型硒催化异氰酸酯和元素硫合成异硫氰酸酯
摘要:通过催化量的元素硒,在温和的条件下,由相应的异氰化物和元素硫以非常好至极佳的收率合成了各种脂肪族和芳香族异硫氰酸酯.
DOI:10.1016/0040-4039(91)80817-P

海关参考信息

专利信息


专利号:WO-2023150820-A1
优先权日:2022-02-10
标题 :Process for the synthesis of radiolabelled biological polymers
发明人:WICHMANN CHRISTIAN WERNER; RUDD STACEY ERIN; SCOTT ANDREW MARK; DONNELLY PAUL STEPHEN
权利人:UNIV MELBOURNE; OLIVIA NEWTON JOHN CANCER RES INSTITUTE
摘要:Processes for the synthesis of zirconium-89 radiolabelled biological polymer-chelate agent conjugates are provided. Radiolabelling is performed in the presence of a polycarboxylate buffer resulting in improved reaction kinetics and short process times. The processes provide a high degree of reproducibility, excellent radiochemical yields and may be automated.

专利号:US-6872727-B1
优先权日:1999-08-26
标 题:Polycyclic pyrimidine -2,4(1H,3H)-diones with functionalized alkyl residues at the 1- and/or 3-position(s); methods for their synthesis and pharmaceutical preparation
发明人:HERRMANN KONRAD; LEISTNER SIEGFRIED; WIPPICH PETRA
权利人:PRIVATES INST FUR BIOMEDIZINIS
摘要:Polycyclic pyrimidine-2,4(1H,3H)-diones with functionalized alkyl residues at the 1-, the 3-, or both position(s); methods for their synthesis, production, and pharmaceutical preparation. The invention concerns the synthesis of the above-described compounds, their chemical and structural characterization, and the analysis of their physiological/pharmacological activities in vitro and in vivo. These goals have been attained by the specification of routes of synthesis, methods for the production of the compounds, and the presentation of compound-specific characteristics. The substances encompassed by the present invention demonstrate pharmacologically significant collangenase/matrix metalloproteinase inhibitory activities. The specific example 1-(3-mercaptoprop-1-yl)-3-methyl-chinazolin-2,4(1H,3H)-dione will be presented in detail.

专利号:WO-2017046598-A1
优先权日:2015-09-16
标题:Treatment of acute inflammatory disorders
发明人:CRISANTI ANDREA; CANAVESE MIRIAM
权利人:CRISANTI ANDREA; IMP INNOVATIONS LTD
摘要:The present invention relates to a VEGF receptor agonist for use in the treatment of an acute inflammatory disorder associated with the overproduction of pro-inflammatory cytokine, administered with an agent that induces the synthesis of Nrf2. The invention also relates to pharmaceutical combinations comprising a VEGF receptor agonist and an agent that induces the synthesis of Nrf2, and kits comprising these agents. The described uses, combinations and methods may prevent or reduce the dis-regulated activation of an inflammatory response and reduce endothelial damage.

专利号:US-10035796-B2
优先权日:2014-08-14
标题:Crystalline forms of a BACE inhibitor, compositions, and their use
发明人:KAZAKEVICH IRINA; TRZASKA SCOTT; FENG TAO
权利人:MERCK SHARP & DOHME
摘要:The present invention provides a novel synthesis of verubecestat, and two novel crystalline forms of verubecestat, as well as pharmaceutically acceptable compositions thereof, each of which may be useful in treating, preventing, ameliorating, and/or delaying the onset of an Aβ pathology and/or a symptom or symptoms thereof. Non-limiting examples of such Aβ pathologies, including Alzheimer's disease, are disclosed herein.

专利号:US-9802952-B2
优先权日:2013-07-15
标 题:Method and apparatus for the synthesis of dihydroartemisinin and artemisinin derivatives
发明人:KOPETZKI DANIEL; MCQUADE DAVID TYLER; SEEBERGER PETER H; GILMORE KERRY
权利人:MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WSS E V; MAX-PLANK-GESELLSCHAFT ZUR FÖRDERUNG DER WSS E V
摘要:The present invention is directed to a method for continuous production of dihydroartemisinin and also artemisinin derivatives derived from dihydroartemisinin by using artemisinin or dihydroartemisinic acid (DHAA) as starting material as well as to a continuous flow reactor for producing dihydroartemisinin as well as the artemisinin derivatives. It was found that the reduction of artemisinin to dihydroartemisinin in a continuous process requires a special kind of reactor and a special combination of reagents comprising a hydride reducing agent, at least one activator such as an inorganic activator, at least one solid base, at least one aprotic solvent and at least one C 1 -C 5 alcohol.

专利号:WO-9700244-A1
优先权日:1995-06-19
标题 :Process for parallel synthesis of a non-peptide library
发明人:FRITZ JAMES E; KALDOR STEPHEN W
权利人:LILLY CO ELI; FRITZ JAMES E; KALDOR STEPHEN W
摘要:A process for the sequential preparation of a library of compounds having pharmaceutical usage. The process involves the sequential mixing of solution phase reagents, followed by scavenging of excess unreacted reagents with solid phase scavenging agents. The process is highly iterative and applicable for producing various ureas, thiureas, amides, carbonates and tertiary amines.
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主要参考文献


1: Dufour V, Stahl M, Rosenfeld E, Stintzi A, Baysse C. Insights into the mode of action of benzyl isothiocyanate on Campylobacter jejuni. Appl Environ Microbiol. 2013 Nov;79(22):6958-68. doi: 10.1128/AEM.01967-13. Epub 2013 Sep 6.
2: De Nicola GR, Montaut S, Rollin P, Nyegue M, Menut C, Iori R, Tatibouët A. Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions. J Agric Food Chem. 2013 Jan 9;61(1):137-42. doi: 10.1021/jf3041534. Epub 2012 Dec 18. doi: 10.1080/09168451.2014.963503. Epub 2014 Sep 25. doi: 10.1158/0008-5472.CAN-15-1544. Epub 2015 Nov 5.
5: Kim M, Cho HJ, Kwon GT, Kang YH, Kwon SH, Her S, Park T, Kim Y, Kee Y, Park JH. Benzyl isothiocyanate suppresses high-fat diet-stimulated mammary tumor progression via the alteration of tumor microenvironments in obesity-resistant BALB/c mice. Mol Carcinog. 2015 Jan;54(1):72-82. doi: 10.1002/mc.22159. Epub 2014 Apr 11. doi: 10.1158/1940-6207.CAPR-13-0242. Epub 2013 Jul 10. doi: 10.1080/01635581.2014.868912. Epub 2014 Jan 21.

合成参考文献


参考文献:10.1080/01635581.2011.589960
摘要:Park E, Cheenpracha S, Chang LC, Kondratyuk TP, Pezzuto JM. Inhibition of Lipopolysaccharide-Induced Cyclooxygenase-2 and Inducible Nitric Oxide Synthase Expression by 4-[(2′-O-acetyl-α-L-Rhamnosyloxy)Benzyl]Isothiocyanate fromMoringa oleifera. Nutrition and Cancer. 2011 Aug;63(6):971–82. doi: 10.1080/01635581.2011.589960.
参考文献:10.1177/1947601911409212
摘要:Basu A, Alder H, Khiyami A, Leahy P, Croce CM, Haldar S. MicroRNA-375 and MicroRNA-221: Potential Noncoding RNAs Associated with Antiproliferative Activity of Benzyl Isothiocyanate in Pancreatic Cancer. Genes & Cancer. 2011 Feb 01;2(2):108–19. doi: 10.1177/1947601911409212.
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