頻那醇硼烷

頻那醇硼烷
	IUPAC名; 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
別名	HBpin
識別
CAS號	25015-63-8
PubChem	6364989
ChemSpider	2016512
SMILES	[B]1OC(C(O1)(C)C)(C)C;
性質
化學式	C6H13BO2
摩爾質量	127.98 g·mol−1
外觀	colorless liquid
密度	0.882 g/cm3
沸點	42-43 °C（272 K）
危險性
	GHS危險性符號;
GHS提示詞	Danger
H-術語	H220, H225, H260, H261, H315, H318
P-術語	P210, P223, P231+232, P233, P240, P241, P242, P243, P264, P280, P302+352, P303+361+353, P305+351+338, P310
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

頻那醇硼烷的結構簡式為(CH₃)₄C₂O₂BH。此硼烷的一個重要特點為,它有一個含硼原子的五元環C₂O₂B。在含硼烷氧基化合物這一類分子中, 頻那醇硼烷為單體。它是無色液體，溶於醚、四氫呋喃以及二氯甲烷等有機溶劑中。^[1] 其反應性很強的B-H基團常被用在有機化學反應中。^[2]

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在有機合成中的應用

頻那醇硼烷被用於將烯烴、炔烴硼氫化，炔烴的硼氫化反應相對較慢。上述反應需要催化劑的存在。^[2]^[3]

頻那醇硼烷也被用在醛^[4]、酮^[5]以及羧酸^[6]的無催化劑硼氫化反應中。

頻那醇硼烷也被用於將有機化合物的C-H鍵硼化，這類反應屬於碳氫鍵活化.^[7]^[8]

頻那醇硼烷的雙分子脫氫反應可以生成雙頻那醇硼烷(B₂pin₂):^[9]

2 (CH₃)₄C₂O₂BH → (CH₃)₄C₂O₂B-BO₂C₂(CH₃)₄ + H₂

參考文獻

[1]
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 (幫助)
[2]
Brown, H.C.; Zaidlewicz, M. Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. 2001. ISBN 978-0-9708441-0-1.
[3]
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 .
[4]
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 （英語）.
[5]
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 （英語）.
[6]
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 （英語）.
[7]
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 (不活躍 31 May 2021).
[8]
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 .
[9]
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 .

[1] [1]
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 (幫助)

[HCC-2] [2]
Brown, H.C.; Zaidlewicz, M. Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. 2001. ISBN 978-0-9708441-0-1.

[3] [3]
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 .

[4] [4]
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 （英語）.

[5] [5]
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 （英語）.

[6] [6]
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 （英語）.

[7] [7]
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 (不活躍 31 May 2021).

[8] [8]
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 .

[9] [9]
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 .

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在有機合成中的應用

相關物質

參考文獻

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頻那醇硼烷