[1]方永勤,武安邦.2,6-二异丙基-4-苯氧基苯基异硫氰酸酯的合成[J].常州大学学报(自然科学版),2012,(04):24-27.
 FANG Yong-qin,WU An-bang.Synthesis of 2,6-Diisopropyl-4-Phenoxyphenyl Isocyanate[J].Journal of Changzhou University(Natural Science Edition),2012,(04):24-27.
点击复制

2,6-二异丙基-4-苯氧基苯基异硫氰酸酯的合成()
分享到:

常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
期数:
2012年04期
页码:
24-27
栏目:
出版日期:
2012-09-30

文章信息/Info

Title:
Synthesis of 2,6-Diisopropyl-4-Phenoxyphenyl Isocyanate
作者:
方永勤武安邦
常州大学 设计研究院,江苏 常州 213164
Author(s):
FANG Yong-qinWU An-bang
Institute of Design and Research,Changzhou University,Changzhou 213164,China
关键词:
26-二异丙基苯胺 26-二异丙基-4-苯氧基苯基异硫氰酸酯 二(三氯甲基)碳酸酯 Ullmann反应
Keywords:
26-Diisopropylaniline 26-Diisopropyl-4-phenoxyphenyl isocyanate Triphosgene Ullmann condensation
分类号:
TQ 454.2
文献标志码:
A
摘要:
以2,6-二异丙基苯胺为原料,经溴化、Ullmann缩合、硫氰化得到2,6-二异丙基-4-苯氧基苯基异硫氰酸酯,并考察了反应条件对收率的影响。较优工艺为,溴化:-5 ℃,n(2,6-二异丙基苯胺):n(Br2)=1.00:1.05; Ullmann缩合:155 ℃,8-羟基喹啉铜为催化剂,n(2,6-二异丙基-4-溴苯胺):n(苯酚):n(KOH)=1.0:1.3:1.2; 硫氰化:70 ℃,n(BTC):n(硫代甲酸盐)=1.0:3.0,3步总收率82.2%。产品结构经IR、1H NMR谱确认。
Abstract:
2,6-Diisopropyl-4-phenoxyphenyl isocyanate was prepared by 2,6-diisopropylaniline via bromation, Ullmann condensation and thiocyanation reaction. The effects of reaction conditions were investigated, andthe optimal conditions were as follows, bromation: at -5 ℃,n(2,6-diisopropylaniline):n(Br2)=1.00:1.05; Ullmann condensation: at 155 ℃, copper 8-hydroxyquinoline as catalyst,n(2,6-diisopropyl-4-bromo aniline):n(phenol):n(KOH)=1.0:1.3:1.2; thiocyanation: at 70 ℃,n(BTC):n(dithiocarbamate)=1.0:3.0, total yieldafter three steps was 82.2%. All compounds obtained were identified by IR and1H NMR.

参考文献/References:

[1]宋玉泉,王军锋.丁醚脲对几种主要害虫的室内生物活性[J].农药,2008,47(8):610-611.
[2]丁从文,张明杰,马宁.硫脲化合物的合成方法研究进展[J].有机化学,2010,30(2),173.
[3]高中良,刘修莲,刘东,等.异硫氰酸酯的合成[J].农药,2009,48(5):322-325.
[4]Phetsuksiri B, Baulard A R, Cooper A M. Antimycobacterial ac-tivities of isoxyl and new derivatives through the Inhibition of mycolic acid synthesis[J].Antimicrobial Agents and Chemo-Theraphy,1999,43(5):1042-1051.
[5]龚银香,王子云,张正文,等.N-(2-羧基-1,3,4-噻二唑-5-基)-N-芳酰基硫脲与芳氧乙酰基硫脲的合成与生物活性[J].有机化学,2006, 26(3):360-363.
[6]何谋海,钟宏,张宝元.异硫氰酸酯及其衍生物的制备和应用进展[J].精细与专用化学品,2010,18(7):9-13.
[7]高宁.异硫氰酸酯化合物在制备治疗白血病的药物中的应用:CN,101474170A[P].2009-07-08.
[8]Drabek J D. Use of N-(4-Phenoxy-2,6-Diisopropylphenyl)-N'-Tert.Butylthiourea in the Control of White Flines:EP,210487[P].1985-07-12.
[9]Robert H. Process of the Preparation of Isothiocyanates:US,4997967[P].1991-03-05.
[10]Mikio Y,Hideo O.Process for Production there of Isothiocyanate Using saidDithiocarbamic Acid Salt:US,5274166[P].1993-12-28.
[11]于宏伟,段书德,刘会茹.2,6-二烷基-4-溴苯胺的合成与表征[J].化学试剂,2009,31(9):757-758.
[12]方永勤,席化远.对氟苯甲酰氯的合成[J].常州大学学报:自然科学版,2012,24(1):18-20.
[13]Alain C, Nikolaus M. Improved Process for the Catalytic Synthesis of Diaryl Ethers:EP,2065357[P].2009-06-03.
[14]潘元佳.铜催化的Ullmann反应研究进展评介[J].化工之友,2007,5(3):44-45.
[15]钱兆生,周传健,曹玲化.糖基异硫氰酸酯的合成及应用[J].化学进展,2006,18(4):430-438.

相似文献/References:

[1]张文楠,黄险峰,宋国强.1,2,3-三-O-乙酰基-5-脱氧-D-呋喃核糖合成工艺研究[J].常州大学学报(自然科学版),2014,(04):16.[doi:10.3969/j.issn.2095-0411.2014.04.004 ]
 ZHANG Wen-nan,HUANG Xian-feng,SONG Guo-qiang.Study of the Synthesis for 1,2,3-Tri-O-Acetyl-5-Deoxy-D-Ribofuranose[J].Journal of Changzhou University(Natural Science Edition),2014,(04):16.[doi:10.3969/j.issn.2095-0411.2014.04.004 ]
[2]吴 霞,单玉华,任海永,等.2,4-二氯苯氧乙酸合成清洁技术研究[J].常州大学学报(自然科学版),2012,(01):10.
 WU Xia,SHAN Yu-hua,REN Hai-yong,et al.Development of a Clean Technique for the Synthesis of 2,4-Dichlorophenoxyacetic Acid[J].Journal of Changzhou University(Natural Science Edition),2012,(04):10.
[3]梁翠荣,金桂花,吴胜楠,等.点击化学应用于合成1,2,3-三唑衍生物的研究进展[J].常州大学学报(自然科学版),2015,(01):54.[doi:10.3969/ j.issn.2095-0411.2015.01.011]
 LIANG Cui-rong,JIN Gui-hua,WU Sheng-nan,et al.Recent Progress in Application of Click Chemistry in the Synthesis of 1,2,3-Triazoles Derivatives[J].Journal of Changzhou University(Natural Science Edition),2015,(04):54.[doi:10.3969/ j.issn.2095-0411.2015.01.011]
[4]邱 滔,范正明,严生虎.2 , 6 -二氯苯腈的合成[J].常州大学学报(自然科学版),2000,(03):36.
 QIU Tao,FAN Zhen -ming,YAN Sheng -hu.Synthesis of 2 , 6-Dichlorobenzonitrile[J].Journal of Changzhou University(Natural Science Edition),2000,(04):36.
[5]王亮,潘亮,陈群,等.酸性离子交换树脂催化4-芳基-1H-1,2,3-三唑的合成[J].常州大学学报(自然科学版),2017,(04):1.[doi:10.3969/j.issn.2095-0411.2017.04.001]
 WANG Liang,PAN Liang,CHEN Qun,et al.Acidic Ion-Exchange Resin-Catalyzed Synthesis of 4-Aryl-1H-1,2,3-Triazoles[J].Journal of Changzhou University(Natural Science Edition),2017,(04):1.[doi:10.3969/j.issn.2095-0411.2017.04.001]
[6]李正义,解广洲,殷乐,等.2,4,8,10-四氧杂螺[5.5]十一烷的结构研究[J].常州大学学报(自然科学版),2018,30(02):1.[doi:10.3969/j.issn.2095-0411.2018.02.001]
 LI Zhengyi,XIE Guangzhou,YIN Yue,et al.Investigation on the Structure of 2,4,8,10-Tetraoxaspiro[5.5]undecanes[J].Journal of Changzhou University(Natural Science Edition),2018,30(04):1.[doi:10.3969/j.issn.2095-0411.2018.02.001]

备注/Memo

备注/Memo:
作者简介:方永勤(1966-),女,江苏姜堰人,研究员级高级工程师。
更新日期/Last Update: 2012-09-30