频那醇硼烷
| 频那醇硼烷 | |
|---|---|
| |
| IUPAC名 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane | |
| 别名 | HBpin |
| 识别 | |
| CAS号 | 25015-63-8 |
| PubChem | 6364989 |
| ChemSpider | 2016512 |
| SMILES |
|
| 性质 | |
| 化学式 | C6H13BO2 |
| 摩尔质量 | 127.98 g·mol−1 |
| 外观 | colorless liquid |
| 密度 | 0.882 g/cm3 |
| 沸点 | 42-43 °C（272 K） |
| 危险性 | |
GHS危险性符号  
| |
| GHS提示词 | Danger |
| H-术语 | H220, H225, H260, H261, H315, H318 |
| P-术语 | P210, P223, P231+232, P233, P240, P241, P242, P243, P264, P280, P302+352, P303+361+353, P305+351+338, P310 |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
频那醇硼烷的结构简式为(CH3)4C2O2BH。 此硼烷的一个重要特点为,它有一个含硼原子的五元环C2O2B。 在含硼烷氧基化合物这一类分子中, 频那醇硼烷为单体。 它是无色液体，溶于醚、四氢呋喃以及二氯甲烷等有机溶剂中。[1] 其反应性很强的B-H基团常被用在有机化学反应中。[2]
在有机合成中的应用
[编辑]频那醇硼烷被用于将烯烃、炔烃硼氢化，炔烃的硼氢化反应相对较慢。上述反应需要催化剂的存在。[2][3]
频那醇硼烷也被用在醛[4]、酮[5]以及羧酸[6]的无催化剂硼氢化反应中。
频那醇硼烷也被用于将有机化合物的C-H键硼化，这类反应属于碳氢键活化.[7][8]
频那醇硼烷的双分子脱氢反应可以生成双频那醇硼烷(B2pin2):[9]
- 2 (CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2
相关物质
[编辑]参考文献
[编辑]- ^ Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Ros, Abel; Fernández, Rosario; Lassaletta, José M.; Aggarwal, Varinder K.; Blair, Daniel J. Encyclopedia of Reagents for Organic Synthesis: 1–12. 2017. ISBN 9780470842898. doi:10.1002/047084289X.rn00574.pub3.
|chapter=被忽略 (帮助) - ^ 2.0 2.1 Brown, H.C.; Zaidlewicz, M. Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. 2001. ISBN 978-0-9708441-0-1.
- ^ Ely, Robert J.; Morken, James P. Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes. Organic Syntheses. 2011, 88: 342. doi:10.15227/orgsyn.088.0342
.
- ^ Stachowiak, Hanna; Kaźmierczak, Joanna; Kuciński, Krzysztof; Hreczycho, Grzegorz. Catalyst-free and solvent-free hydroboration of aldehydes. Green Chemistry. 2018, 20 (8): 1738–1742. ISSN 1463-9262. doi:10.1039/C8GC00042E （英语）.
- ^ Wang, Weifan; Luo, Man; Yao, Weiwei; Ma, Mengtao; Pullarkat, Sumod A.; Xu, Li; Leung, Pak-Hing. Catalyst-free and solvent-free hydroboration of ketones. New Journal of Chemistry. 2019, 43 (27): 10744–10749. ISSN 1144-0546. doi:10.1039/C9NJ02722J （英语）.
- ^ Harinath, Adimulam; Bhattacharjee, Jayeeta; Panda, Tarun K. Facile Reduction of carboxylic acids to primary alcohols under catalyst-free and solvent-free conditions. Chemical Communications. 2019, 55 (10): 1386–1389. ISSN 1359-7345. PMID 30607398. doi:10.1039/C8CC08841A （英语）.
- ^ Amaike, K.; Loach, R. P.; Movassaghi, M. Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate. Organic Syntheses. 2015, 92: 373–385. PMC 4733874 . PMID 26839440. doi:10.15227/orgsyn.092.0373 (不活跃 31 May 2021).
- ^ Ishiyama, Tatsuo; Takagi, Jun; Nobuta, Yusuke; Miyaura, Norio. Iridium-Catalyzed C-H Borylation of Arenes and Heteroarenes: 1-Chloro-3-Iodo-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzene and 2-(4,4,5,5,-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Indole. Organic Syntheses. 2005, 82: 126. doi:10.15227/orgsyn.082.0126. hdl:2115/56319 .
- ^ Neeve, Emily C.; Geier, Stephen J.; Mkhalid, Ibraheem A. I.; Westcott, Stephen A.; Marder, Todd B. Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse. Chemical Reviews. 2016, 116 (16): 9091–9161. PMID 27434758. doi:10.1021/acs.chemrev.6b00193 .
