Synthesis and Characterization of 1,3,5,7-Tetraisocyanatoethyl-1,3,5,7-tetramethylcyclotetrasiloxane

doi:10.6023/cjoc201308024

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 596-599.DOI: 10.6023/cjoc201308024 Previous Articles Next Articles

Reviews

1,3,5,7-四异氰氧基乙基-1,3,5,7-四甲基环四硅氧烷合成及结构表征

吴林^a, 臧雄^a, 阎四海^b, 唐松青^b, 李战雄^a

a 苏州大学纺织与服装工程学院苏州 215021;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2013-08-27 修回日期:2013-10-23 发布日期:2013-11-05
通讯作者: 李战雄 E-mail:lizhanxiong@163.com
基金资助:
国家自然科学基金（No. 51273140）资助项目.

Synthesis and Characterization of 1,3,5,7-Tetraisocyanatoethyl-1,3,5,7-tetramethylcyclotetrasiloxane

Wu Lin^a, Zang Xiong^a, Yan Sihai^b, Tang Songqing^b, Li Zhanxiong^a

a College of Textile and Clothing Engineering, Soochow University, Suzhou 215021;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2013-08-27 Revised:2013-10-23 Published:2013-11-05
Supported by:
Project supported by the National Natural Science Foundation of China (No. 51273140).

1,3,5,7-Tetra(trimethylsiloxysilicatecarboxypropyl)-1,3,5,7-tetramethylcyclotetrasiloxane (2) was prepared by esterification and hydrosilylation reaction using acrylic acid and 1,3,5,7-tetramethylcyclotetrasiloxane (D₄H) as raw materials. 2 was hydrolyzed to obtain 1,3,5,7-tetracarboxypropyl-1,3,5,7-tetramethylcyclotetrasiloxane (3) followed by Staudinger reaction and Curtius rearrangement reaction to give 1,3,5,7-tetraisocyanatoethyl-1,3,5,7-tetramethylcyclotetrasiloxane (4) with the total yield of 14.5%. The structure of cyclosiloxane was characterized by ¹H NMR, ²⁹Si NMR, IR, MS and HR-MS techniques.

Key words: synthesis, curtius rearrangement, cyclosiloxane, isocyanate

Cite this article

Wu Lin, Zang Xiong, Yan Sihai, Tang Songqing, Li Zhanxiong. Synthesis and Characterization of 1,3,5,7-Tetraisocyanatoethyl-1,3,5,7-tetramethylcyclotetrasiloxane[J]. Chin. J. Org. Chem., 2014, 34(3): 596-599.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Kim, E. S.; Kim, E. J.; Lee, T. H.; Yoon, J. S. J. Appl. Polym. Sci. 2013, 128, 2563.

[2] Kim, E. S.; Kim, H. S.; Jung, S. H.; Yoon, J. S. J. Appl. Polym. Sci. 2007, 103, 2782.

[3] Koβmehl, G.; Neumann, W. Makromol. Chem. 1986, 187, 1371.

[4] Noble, K. L. Prog. Org. Coat. 1997, 32, 135.

[5] Hu, Y.-G.; Xu, J.; Chen, X.-B.; Qu, Y.-N. Chin. J. Org. Chem. 2009, 29(11), 1854 (in Chinese).

(胡扬根, 徐靖, 陈小保, 屈永年, 有机化学, 2009, 29(11), 1854.)

[6] Sun, Y.; Ding, M.-W.; Liu, Z.-J. Chin. J. Org. Chem. 2003, 23(8), 818 (in Chinese).

(孙勇, 丁明武, 刘钊杰. 有机化学, 2003, 23(8), 818.)

[7] Zhang, C.-Y.; Zhang, X.-Y.; Dai, J.-B.; Bai, C.-Y. Prog. Org. Coat. 2008, 63, 239.

[8] Suyama, K.; Gunji, T.; Arimitsu, K.; Abe, Y. J. Organomet. 2006, 25, 5587.

[9] Wang, L.; Shen, Y.-D.; Lai, X.-J.; Li, Z.-J.; Liu, M. J. Polym. Res. 2011, 18, 469.

[10] Rahman, M. M.; Chun, H. H.; Park, H. J. Coat. Technol. Res. 2011, 8(3), 389.

[11] Yen, M. S.; Tsai, P. Y.; Hong, P. D. Colloids Surf., A 2006, 279, 1.

[12] Qing, Y.-J.; Quan, Y.-W.; Zhang, J.-S.; Chen, Q.-M. J. Nanjing Univ. (Nat. Sci.) 2002, 38(2), 205 (in Chinese).

(秦玉军, 全一武, 张俊生, 陈庆民, 南京大学学报, 2002, 38(2), 205.)

[13] Jiang, X.-B.; Zhu, X.-L.; Zhang, Z.; Kong, X.-Z. Acta Chim. Sinica 2011, 69(9), 1117 (in Chinese).

(姜绪宝, 朱晓丽, 张召, 孔祥正, 化学学报, 2011, 69(9), 1117.)

[14] Sow, C.; Riedl, B.; Blanchet, P. J. Coat. Technol. Res. 2011, 8(2), 211.

[15] Pathak, S. S.; Sharma, A.; Khanna, A. S. Prog. Org. Coat. 2009, 65, 207.

[16] Sarkar, S. D.; Studer, A. Org. Lett. 2010, 12(9), 1995.

[17] Arote, N. D.; Akamanchi, K. G. Tetrahedron Lett. 2007, 48, 5662.

[18] Sprecher, H.; Pérez-Payán, M. N.; Weber, M.; Yilmaz, G.; Wille, G. J. Flow Chem. 2012, 1, 21.

[19] Nowrouzi, N.; Jonaghani, M. Z. Chin. Chem. Lett. 2012, 23, 443.

[20] Swetha, M.; Ramana, P. V.; Shirodkar, S. G. Org. Prep. Proced. Int. 2011, 43, 349.

[21] Lai, G.-Q. Organic Silicon Chemistry and Technology, Chemical Industry Press, Beijing, 2011, p. 28 (in Chinese).

(来国桥, 有机硅化学与工艺, 化学工业出版社, 北京, 2011, p. 28.)

[22] Woodward, K. J.; Edmund, R. M. EP 0196169, 1993[Chem. Abstr. 1986, 106, 20115].

[23] Stute, A.; Heletta, L.; Frohlich, R.; Daniliuc, C. G.; Kehr, G.; Erker, G.; Chem. Commun. 2012, 48, 11739.

[24] Bellucci, M. C.; Volonterio, A. Tetrahedron Lett. 2012, 53, 4735.

[25] Akhlaghinia, B.; Rouhi-Saadabad, H. Can. J. Chem. 2013, 91, 182.

[26] Froeyen, P. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 89(1～4), 57.

[27] Banert, K.; Berndt, C.; Hagedorn, M.; Liu, H. L.; Anacker, T.; Friedrich, J.; Rauhut, G. Angew. Chem. Int. Ed. 2012, 51, 4718.

[28] Mujde, N.; Ozcan, S.; Balci, M. Phytochem. Lett. 2011, 4, 408.

[29] Tarwade, V.; Dmitrenko, O.; Bach, R. D.; Fox, J. M. J. Org. Chem. 2008, 73, 8189.

[30] Wang, X.; Li, J.-Z.; Zhao, N.; Wan, X.-B. Org. Lett. 2011, 13(4), 710.

[31] Ma, B.; Lee, W. C. Tetrahedron Lett. 2010, 51, 386.

1,3,5,7-四异氰氧基乙基-1,3,5,7-四甲基环四硅氧烷合成及结构表征

Synthesis and Characterization of 1,3,5,7-Tetraisocyanatoethyl-1,3,5,7-tetramethylcyclotetrasiloxane

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[6]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[7]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[8]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[9]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[10]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[11]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.