| 词条 | Vinylcyclohexene dioxide |
| 释义 |
| ImageFile = Vinylcyclohexendioxid.svg | ImageAlt = Molecular structure of vinylcyclohexene dioxide | IUPACName = 3-Oxiranyl-7-oxabicyclo[4.1.0]heptane | OtherNames = 1,2-Epoxy-4-(epoxyethyl)cyclohexane 4-Vinylcyclohexene diepoxide |Section1={{Chembox Identifiers | CASNo = 106-87-6 | PubChem = 7833 | SMILES = C1CC2C(O2)CC1C3CO3 | Abbreviations = VCD |Section2={{Chembox Properties | C=8 | H=12 | O=2 | Appearance = Colorless liquid[1] | Density = 1.09 g·cm−3[2][3] | MeltingPtC = -108.9 | MeltingPt_ref = [4] | BoilingPtC = 227 | BoilingPt_ref = [4] | Solubility = | VaporPressure = 13 Pa (20 °C)[4] |Section3={{Chembox Hazards | MainHazards = Toxic | FlashPt = | AutoignitionPt = }}4-Vinylcyclohexene dioxide (VCD) is an organic compound that contains two epoxide functional groups. It is industrially used as a crosslinking agent for the production of epoxy resins.[7][5] It is a colourless liquid. It is an intermediate for synthesis of organic compounds.[2] Preparation and properties4-Vinylcyclohexene dioxide is prepared by epoxidation of 4-vinylcyclohexene with peroxybenzoic acid.[6] Its viscosity is 15 mPa·s.[6] Safety4-Vinylcyclohexene dioxide, like other volatile epoxides, is classified as an alkylating agent.[6] VCD has toxic effects on fertility. It is a killer of oocytes in immature ovarian follicles in mice and rats.[7][8][9] In pest control, it has been used as an ovotoxic agent for reducing rat fertility.[10] References1. ^{{cite journal |author =Kam-Piu Ho, Wing-Leung Wong, Kin-Ming Lam, Cheuk-Piu Lai, Tak Hang Chan und Kwok-Yin Wong |title=A Simple and Effective Catalytic System for Epoxidation of Aliphatic Terminal Alkenes with Manganese(II) as the Catalyst|journal=Chemistry: A European Journal|date=2008-09-08|volume=14|issue=26|pages=7988–7996|doi=10.1002/chem.200800759}} 2. ^1 {{cite journal |author = Kh. M. Alimardanov, O. A. Sadygov, N. I. Garibov und M. Ya. Abdullaeva |title = Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide |journal = Russian Journal of Organic Chemistry |date = 2012-11-07|volume = 48|issue = 10|pages = 1302–1308|doi = 10.1134/S1070428012100077}} 3. ^{{cite journal |author = L. A. Mukhamedova, G. Kh. Gil'manova, M. I. Kudryavtseva, F. G. Nasybullina und A. S. Kireeva |title = Synthesis and testing of the antiviral activity of epoxy and triazo derivatives of cyclohexane|journal = Pharmaceutical Chemistry Journal|date = July 1982|volume = 16|issue = 7|pages = 510–514|doi = 10.1007/BF00761540}} 4. ^1 2 {{GESTIS|ZVG=510220 |CAS=106-87-6 |Name= |Date= 24. März 2015}} 5. ^{{patent|US|2555500|"Copolymers of 4-vinylcyclohexene dioxide."|Hart Segall Gordon filing date 25.01.1949}} 6. ^1 2 3 {{cite journal|last1=Pham|first1=Ha Q.|last2=Marks|first2=Maurice J.|title=Epoxy Resins|journal=Ullmann's Encyclopedia of Industrial Chemistry|doi=10.1002/14356007.a09_547.pub2}} 7. ^{{Cite journal|last=Kappeler|first=Connie J.|last2=Hoyer|first2=Patricia B.|date=2012-02-01|title=4-vinylcyclohexene diepoxide: a model chemical for ovotoxicity|journal=Systems Biology in Reproductive Medicine|volume=58|issue=1|pages=57–62|doi=10.3109/19396368.2011.648820|issn=1939-6376|pmc=3307534|pmid=22239082}} 8. ^{{Cite journal|last=Takai|first=Yasushi|last2=Canning|first2=Jacqueline|last3=Perez|first3=Gloria I.|last4=Pru|first4=James K.|last5=Schlezinger|first5=Jennifer J.|last6=Sherr|first6=David H.|last7=Kolesnick|first7=Richard N.|last8=Yuan|first8=Junying|last9=Flavell|first9=Richard A.|date=2003-01-01|title=Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo|journal=Endocrinology|volume=144|issue=1|pages=69–74|doi=10.1210/en.2002-220814|issn=0013-7227|pmid=12488331}} 9. ^{{Cite journal|last=Hoyer|first=P. B.|last2=Devine|first2=P. J.|last3=Hu|first3=X.|last4=Thompson|first4=K. E.|last5=Sipes|first5=I. G.|date=2001-02-01|title=Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model|journal=Toxicologic Pathology|volume=29|issue=1|pages=91–99|issn=0192-6233|pmid=11215690}} 10. ^{{cite journal | journal = Toxicol Pathol.|date = Jan–Feb 2001|volume = 29|issue = 1|pages = 91-99|title = Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model|authors = Hoyer PB1, Devine PJ, Hu X, Thompson KE, Sipes IG}} 3 : Epoxides|Cyclohexanes|Monomers |
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