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维基百科

2,3-环氧丁烷

十月 07, 2023

2,3-环氧丁烷（英語：2,3-Epoxybutane）是化学式为CH3CH(O)CHCH3的环氧化合物，带有两个手性碳原子，其中的(2R,3S)-2,3-环氧丁烷为内消旋化合物，因此总共有三种立体异构体，它们都是无色液体。

2,3-环氧丁烷
IUPAC名
2,3-Dimethyloxirane
别名 2,3-二甲基环氧乙烷
2-丁烯环氧化物
识别
CAS号 3266-23-7  
1758-33-4（R,S）  
21490-63-1（S,S）  
1758-32-3（R,R）  
PubChem 18632
92162
30664
6432237
SMILES
 
  • CC1C(O1)C
InChI
 
  • 1S/C4H8O/c1-3-4(2)5-3/h3-4H,1-2H3
InChIKey PQXKWPLDPFFDJP-UHFFFAOYSA-N
UN编号 3271
性质
化学式 C4H8O
摩尔质量 72.11 g·mol−1
外观 无色液体
密度 0.837 g·cm−3
熔点 −85 °C（188 K）（S,S）[1]
−80 °C（193 K）（R,S）[1]
沸点 55－56 °C（328－329 K）[2]
56.5 °C（329.6 K）（S,S）[1]
60 °C（333 K）（R,S）[3]
53.5 °C（326.6 K）（746 torr，R,R）[4]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成 编辑

2,3-环氧丁烷可由2-丁烯为原料进行合成，反应会生成中间体卤代醇（英语：Halohydrin）[5]：

CH3CH=CHCH3 + HOCl → CH3CH(OH)CH(Cl)CH3
CH3CH(OH)CH(Cl)CH3 → CH3CH(O)CHCH3 + HCl

2,3-丁二醇在偶氮二甲酸二乙酯和三苯基膦的存在下脱水环化，也可以得到2,3-环氧丁烷。[6]

性质 编辑

2,3-环氧丁烷的三元环不稳定，可以发生开环反应，如氢化生成对应的2,3-丁二醇[7]。它和溴代甲硼烷二甲硫醚反应，可以得到3-溴-2-丁醇。[8]在二甲基氧鎓四氟硼酸盐催化下，二甲基亚砜可将其氧化为3-羟基-2-丁酮。[9]

它和二氧化碳发生环加成反应，生成2,3-丁二醇-2,3-环碳酸酯，反应所用的催化剂已有较多报道，如氨基酸-碘化钾[10]、金属有机框架材料[11]等。它和二硫化碳反应，生成2,3-丁二醇-2O,3S-二硫代环碳酸酯。[12]

 
 

2,3-环氧丁烷和五氧化二氮在二氯甲烷中反应，得到2,3-丁二醇-2,3-二硝酸酯；[13]和四硝基甲烷反应，得到2,3-丁二醇-2-硝酸酯。[14]它和三甲基氰硅烷发生开环反应，得到2-甲基-3-三甲基硅氧基丁腈。[15]它和O-异丙基-O-苯基硒代磷酸反应，得到2-异丙基-4,5-二甲基-1,3,2-氧杂硒杂磷杂环戊烷-2-氧化物。[16]

参考文献 编辑

  1. ^ 1.0 1.1 1.2 "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-10].
  2. ^ Cottle, D. L.; Powell, Leo S. The Reaction of 2,3-Epoxybutane with the Grignard Reagent. Journal of the American Chemical Society. 2002, 58 (11): 2267–2272. ISSN 0002-7863. doi:10.1021/ja01302a052. 
  3. ^ Farberov, M. I.; Bondarenko, A. V.; Obukhov, V. M.; Stepanova, I. P.; Srednev, S. S.; Vasil'eva, I. A. Epoxidation of 2-butene by organic hydroperoxides and syntheses based on 2-butene oxide. II. Syntheses based on 2-butene oxide（俄文）. Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1984. 57 (11): 2581-2584. ISSN: 0044-4618. CODEN: ZPKHAB.
  4. ^ Leroux, P. J.; Lucas, H. J. L(-)-2-Butanol from D(-)-2,3-Butanediol. Journal of the American Chemical Society. 2002, 73 (1): 41–42. ISSN 0002-7863. doi:10.1021/ja01145a015. 
  5. ^ Heinz Gräfje, Wolfgang Körnig, Hans-Martin Weitz, Wolfgang Reiß, Guido Steffan, Herbert Diehl, Horst Bosche, Kurt Schneider and Heinz Kieczka "Butanediols, Butenediol, and Butynediol" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a04_455
  6. ^ Castro, Bertrand R. Replacement of Alcoholic Hydroxyl Groups by Halogens and Other Nucleophiles via Oxyphosphonium Intermediates: 18. 2005. doi:10.1002/0471264180.or029.01. 
  7. ^ Nugent, William A. Desymmetrization of Meso Epoxides with Halides: A New Catalytic Reaction Based on Mechanistic Insight. Journal of the American Chemical Society. 1998, 120: 7139–7140. doi:10.1021/JA981031L. 
  8. ^ Brown, Herbert C.; Roy, Chandra Deo. Dibromoborane-Dimethyl Sulfide and Monobromoborane-Dimethyl Sulfide as Superior Reagents for the Opening of Oxiranes to Bromohydrins. Molecules Online. 1998, 2 (8): 114–120. ISSN 1433-1373. doi:10.1007/s007830050066. 
  9. ^ Tsuji, Tadakazu. Acid-Catalyzed Oxidation of Oxiranes with Dimethyl Sulfoxide Giving α-Hydroxy Ketones. Bulletin of the Chemical Society of Japan. 1989, 62 (2): 645–647. ISSN 0009-2673. doi:10.1246/bcsj.62.645. 
  10. ^ Yang, Zifeng; Sun, Jian; Cheng, Weiguo; Wang, Jinquan; Li, Qian; Zhang, Suojiang. Biocompatible and recyclable amino acid binary catalyst for efficient chemical fixation of CO2. Catalysis Communications. 2014, 44: 6–9. ISSN 1566-7367. doi:10.1016/j.catcom.2013.07.025. 
  11. ^ Parmar, Bhavesh; Patel, Parth; Pillai, Renjith S.; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Suresh, Eringathodi. Efficient catalytic conversion of terminal/internal epoxides to cyclic carbonates by porous Co(ii) MOF under ambient conditions: structure–property correlation and computational studies. Journal of Materials Chemistry A. 2019, 7 (6): 2884–2894. ISSN 2050-7488. doi:10.1039/C8TA10631B. 
  12. ^ Pielichowski, Jan; Czub, Piotr. Preparation of substituted 1,3-oxothiolane-2-thiones by reacting epoxides with carbon disulfide（波兰文）. 2006. PL 191028 B1.
  13. ^ Golding, P.; W Millar, R; C Paul, N; H Richards (deceased), D. Nitration by oxides of nitrogen, part 1: preparation of nitrate esters by reaction of strained-ring oxygen heterocycles with dinitrogen pentoxide. Tetrahedron Letters. 1988, 29 (22): 2731–2734. ISSN 0040-4039. doi:10.1016/0040-4039(88)85272-9. 
  14. ^ Volkova, Yuliya A.; Ivanova, Olga A.; Budynina, Ekaterina M.; Averina, Elena B.; Kuznetsova, Tamara S.; Zefirov, Nikolai S. Tetranitromethane as an efficient reagent for the conversion of epoxides into β-hydroxy nitrates. Tetrahedron Letters. 2008, 49 (24): 3935–3938. ISSN 0040-4039. doi:10.1016/j.tetlet.2008.04.050. 
  15. ^ Lidy, Werner; Sundermeyer, Wolfgang. Cleavage reactions of trimethylsilyl cyanide with epoxides, carboxylic acid chlorides, chlorocarbonate esters, and sulfenyl chlorides（德文）. Tetrahedron Letters, 1973. 9 (17): 1449-1450. ISSN: 0040-4039. CODEN: TELEAY.
  16. ^ Arbuzov, B. A.; Nuretdinova, O. N. Reactions of diaryl thio- and selenophosphoric acids with oxetanes（俄文）. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983. 3. 675-677. ISSN: 0002-3353. CODEN: IASKA6.

十月 07, 2023
环氧丁烷, 英語, epoxybutane, 是化学式为ch3ch, chch3的环氧化合物, 带有两个手性碳原子, 其中的, 为内消旋化合物, 因此总共有三种立体异构体, 它们都是无色液体, iupac名2, dimethyloxirane别名, 二甲基环氧乙烷2, 丁烯环氧化物识别cas号, 3266, 1758, 21490, 1758, pubchem, 18632, 92162, 30664, 6432237smiles, cc1c, cinchi, c4h8o, 2h3inchikey, pqxkwpl. 2 3 环氧丁烷 英語 2 3 Epoxybutane 是化学式为CH3CH O CHCH3的环氧化合物 带有两个手性碳原子 其中的 2R 3S 2 3 环氧丁烷为内消旋化合物 因此总共有三种立体异构体 它们都是无色液体 2 3 环氧丁烷IUPAC名2 3 Dimethyloxirane别名 2 3 二甲基环氧乙烷2 丁烯环氧化物识别CAS号 3266 23 7 1758 33 4 R S 21490 63 1 S S 1758 32 3 R R PubChem 18632 92162 30664 6432237SMILES CC1C O1 CInChI 1S C4H8O c1 3 4 2 5 3 h3 4H 1 2H3InChIKey PQXKWPLDPFFDJP UHFFFAOYSA NUN编号 3271性质化学式 C4H8O摩尔质量 72 11 g mol 1外观 无色液体密度 0 837 g cm 3熔点 85 C 188 K S S 1 80 C 193 K R S 1 沸点 55 56 C 328 329 K 2 56 5 C 329 6 K S S 1 60 C 333 K R S 3 53 5 C 326 6 K 746 torr R R 4 若非注明 所有数据均出自标准状态 25 100 kPa 下 合成 编辑2 3 环氧丁烷可由2 丁烯为原料进行合成 反应会生成中间体卤代醇 英语 Halohydrin 5 CH3CH CHCH3 HOCl CH3CH OH CH Cl CH3 CH3CH OH CH Cl CH3 CH3CH O CHCH3 HCl2 3 丁二醇在偶氮二甲酸二乙酯和三苯基膦的存在下脱水环化 也可以得到2 3 环氧丁烷 6 性质 编辑2 3 环氧丁烷的三元环不稳定 可以发生开环反应 如氢化生成对应的2 3 丁二醇 7 它和溴代甲硼烷二甲硫醚反应 可以得到3 溴 2 丁醇 8 在二甲基氧鎓四氟硼酸盐催化下 二甲基亚砜可将其氧化为3 羟基 2 丁酮 9 它和二氧化碳发生环加成反应 生成2 3 丁二醇 2 3 环碳酸酯 反应所用的催化剂已有较多报道 如氨基酸 碘化钾 10 金属有机框架材料 11 等 它和二硫化碳反应 生成2 3 丁二醇 2O 3S 二硫代环碳酸酯 12 nbsp nbsp 2 3 环氧丁烷和五氧化二氮在二氯甲烷中反应 得到2 3 丁二醇 2 3 二硝酸酯 13 和四硝基甲烷反应 得到2 3 丁二醇 2 硝酸酯 14 它和三甲基氰硅烷发生开环反应 得到2 甲基 3 三甲基硅氧基丁腈 15 它和O 异丙基 O 苯基硒代磷酸反应 得到2 异丙基 4 5 二甲基 1 3 2 氧杂硒杂磷杂环戊烷 2 氧化物 16 参考文献 编辑 1 0 1 1 1 2 PhysProp data were obtained from Syracuse Research Corporation of Syracuse New York US Retrieved from SciFinder 2021 07 10 Cottle D L Powell Leo S The Reaction of 2 3 Epoxybutane with the Grignard Reagent Journal of the American Chemical Society 2002 58 11 2267 2272 ISSN 0002 7863 doi 10 1021 ja01302a052 Farberov M I Bondarenko A V Obukhov V M Stepanova I P Srednev S S Vasil eva I A Epoxidation of 2 butene by organic hydroperoxides and syntheses based on 2 butene oxide II Syntheses based on 2 butene oxide 俄文 Zhurnal Prikladnoi Khimii Sankt Peterburg Russian Federation 1984 57 11 2581 2584 ISSN 0044 4618 CODEN ZPKHAB Leroux P J Lucas H J L 2 Butanol from D 2 3 Butanediol Journal of the American Chemical Society 2002 73 1 41 42 ISSN 0002 7863 doi 10 1021 ja01145a015 Heinz Grafje Wolfgang Kornig Hans Martin Weitz Wolfgang Reiss Guido Steffan Herbert Diehl Horst Bosche Kurt Schneider and Heinz Kieczka Butanediols Butenediol and Butynediol in Ullmann s Encyclopedia of Industrial Chemistry 2000 Wiley VCH Weinheim doi 10 1002 14356007 a04 455 Castro Bertrand R Replacement of Alcoholic Hydroxyl Groups by Halogens and Other Nucleophiles via Oxyphosphonium Intermediates 18 2005 doi 10 1002 0471264180 or029 01 Nugent William A Desymmetrization of Meso Epoxides with Halides A New Catalytic Reaction Based on Mechanistic Insight Journal of the American Chemical Society 1998 120 7139 7140 doi 10 1021 JA981031L Brown Herbert C Roy Chandra Deo Dibromoborane Dimethyl Sulfide and Monobromoborane Dimethyl Sulfide as Superior Reagents for the Opening of Oxiranes to Bromohydrins Molecules Online 1998 2 8 114 120 ISSN 1433 1373 doi 10 1007 s007830050066 Tsuji Tadakazu Acid Catalyzed Oxidation of Oxiranes with Dimethyl Sulfoxide Giving a Hydroxy Ketones Bulletin of the Chemical Society of Japan 1989 62 2 645 647 ISSN 0009 2673 doi 10 1246 bcsj 62 645 Yang Zifeng Sun Jian Cheng Weiguo Wang Jinquan Li Qian Zhang Suojiang Biocompatible and recyclable amino acid binary catalyst for efficient chemical fixation of CO2 Catalysis Communications 2014 44 6 9 ISSN 1566 7367 doi 10 1016 j catcom 2013 07 025 Parmar Bhavesh Patel Parth Pillai Renjith S Kureshy Rukhsana I Khan Noor ul H Suresh Eringathodi Efficient catalytic conversion of terminal internal epoxides to cyclic carbonates by porous Co ii MOF under ambient conditions structure property correlation and computational studies Journal of Materials Chemistry A 2019 7 6 2884 2894 ISSN 2050 7488 doi 10 1039 C8TA10631B Pielichowski Jan Czub Piotr Preparation of substituted 1 3 oxothiolane 2 thiones by reacting epoxides with carbon disulfide 波兰文 2006 PL 191028 B1 Golding P W Millar R C Paul N H Richards deceased D Nitration by oxides of nitrogen part 1 preparation of nitrate esters by reaction of strained ring oxygen heterocycles with dinitrogen pentoxide Tetrahedron Letters 1988 29 22 2731 2734 ISSN 0040 4039 doi 10 1016 0040 4039 88 85272 9 Volkova Yuliya A Ivanova Olga A Budynina Ekaterina M Averina Elena B Kuznetsova Tamara S Zefirov Nikolai S Tetranitromethane as an efficient reagent for the conversion of epoxides into b hydroxy nitrates Tetrahedron Letters 2008 49 24 3935 3938 ISSN 0040 4039 doi 10 1016 j tetlet 2008 04 050 Lidy Werner Sundermeyer Wolfgang Cleavage reactions of trimethylsilyl cyanide with epoxides carboxylic acid chlorides chlorocarbonate esters and sulfenyl chlorides 德文 Tetrahedron Letters 1973 9 17 1449 1450 ISSN 0040 4039 CODEN TELEAY Arbuzov B A Nuretdinova O N Reactions of diaryl thio and selenophosphoric acids with oxetanes 俄文 Izvestiya Akademii Nauk SSSR Seriya Khimicheskaya 1983 3 675 677 ISSN 0002 3353 CODEN IASKA6 取自 https zh wikipedia org w index php title 2 3 环氧丁烷 amp oldid 76860527, 维基百科，wiki，书籍，书籍，图书馆，

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