2,3-环氧丁烷(英语: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。
Quick Facts 2,3-环氧丁烷, 识别 ...
2,3-环氧丁烷
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IUPAC名 2,3-Dimethyloxirane
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别名
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2,3-二甲基环氧乙烷 2-丁烯环氧化物
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识别
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CAS号
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3266-23-7 Y 1758-33-4(R,S) Y 21490-63-1(S,S) Y 1758-32-3(R,R) Y
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PubChem
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18632 92162 30664 6432237
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SMILES
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InChI
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- 1S/C4H8O/c1-3-4(2)5-3/h3-4H,1-2H3
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InChIKey
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PQXKWPLDPFFDJP-UHFFFAOYSA-N
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UN编号
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3271
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性质
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化学式
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C4H8O
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摩尔质量
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72.11 g·mol−1
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外观
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无色液体
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密度
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0.837 g·cm−3
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熔点
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−85 °C(188 K)(S,S)[1] −80 °C(193 K)(R,S)[1]
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沸点
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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]
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若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。
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Close
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]
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]在二甲基氧𬭩四氟硼酸盐催化下,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]
![Thumb](//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/2%2C3-Epoxybutane_CO2_cycloaddition.png/320px-2%2C3-Epoxybutane_CO2_cycloaddition.png)
![Thumb](//upload.wikimedia.org/wikipedia/commons/thumb/3/31/2%2C3-Epoxybutane_CS2_cycloaddition.png/320px-2%2C3-Epoxybutane_CS2_cycloaddition.png)
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]
"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-10].
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