2,3-环氧丁烷

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。

2,3-环氧丁烷（英語：）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，它们都是无色液体。

合成

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[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

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

"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. . 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. . Journal of the American Chemical Society. 2002, 73 (1): 41–42. ISSN 0002-7863. doi:10.1021/ja01145a015.
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
Castro, Bertrand R. : 18. 2005. doi:10.1002/0471264180.or029.01.
Nugent, William A. . Journal of the American Chemical Society. 1998, 120: 7139–7140. doi:10.1021/JA981031L.
Brown, Herbert C.; Roy, Chandra Deo. . Molecules Online. 1998, 2 (8): 114–120. ISSN 1433-1373. doi:10.1007/s007830050066.
Tsuji, Tadakazu. . 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. . 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. . 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. . 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. . 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.

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[SRC-1] "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. . 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. . Journal of the American Chemical Society. 2002, 73 (1): 41–42. ISSN 0002-7863. doi:10.1021/ja01145a015.

[Ullmann-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. : 18. 2005. doi:10.1002/0471264180.or029.01.

[7] Nugent, William A. . Journal of the American Chemical Society. 1998, 120: 7139–7140. doi:10.1021/JA981031L.

[8] Brown, Herbert C.; Roy, Chandra Deo. . Molecules Online. 1998, 2 (8): 114–120. ISSN 1433-1373. doi:10.1007/s007830050066.

[9] Tsuji, Tadakazu. . 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. . 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. . 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. . 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. . 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.