6-溴-1-己醇

6-溴-1-己醇
英文名	6-bromo-1-hexanol
别名	6-溴正己醇; ω-溴-1-己醇
识别
CAS号	4286-55-9
PubChem	77970
SMILES	BrCCCCCCO;
性质
化学式	C6H13BrO
摩尔质量	181.07 g·mol−1
密度	1.3628 g·cm−3（20 °C）
沸点	105—106 °C（378—379 K）（5 Torr）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

6-溴-1-己醇是一种有机化合物，化学式为Br(CH₂)₆OH。它可由1,6-己二醇和氢溴酸回流得到。^[3]

反应

6-溴-1-己醇和叠氮化钠在N,N-二甲基甲酰胺中反应，可以得到6-叠氮基-1-己醇。^[4]

6-溴-1-己醇和苯酚在碳酸钾的存在下（碘化钾催化）于丙酮中反应，可以得到6-苯氧基-1-己醇；^[5]它和二乙胺在相似条件下于N,N-二甲基甲酰胺中反应，得到6-二乙氨基-1-己醇。^[6]它和三苯基膦在乙腈中反应，得到季𬭸盐(6-羟己基)三苯基溴化𬭸。^[7]

6-溴-1-己醇和联硼酸频哪醇酯在氯化三(三苯基膦)合钴(I)的催化下反应，生成羟己基硼酸频哪醇酯，可用作有机试剂。^[8]

该化合物有羟基，具有醇的通性。如和乙酰氯发生酯化反应，生成乙酸-6-溴己酯^[9]；可以被PCC等氧化剂氧化为相应的醛^[10]等。

参考文献

^ Kurbanli, Kamuran; Ahmetli, Gulnare; Tarlan, Esra. Synthesis of biologically active and environmental friendly insect pesticides: pheromones. Asian Journal of Chemistry, 2009. 21 (3): 1903-1909. ISSN: 0970-7077.
^ Degering, Ed. F.; Boatright, Leslie G. Studies on the Synthesis of Lysine1. Journal of the American Chemical Society. 1950, 72 (11): 5137–5139. ISSN 0002-7863. doi:10.1021/ja01167a091.
^ Oliveira, Adeildo Junior; Souza, Isis Torres; Bernardo, Vanderson Barbosa; Santos, Larissa C.; Lima, Maria Raquel Ferreira; Goulart, Henrique Fonseca; Goulart Santana, Antônio Euzébio. Monobromination of α, ω‐Diols: Highly Efficient Preparation of Synthetic Intermediates. ChemistrySelect. 2019, 4 (36): 10843–10845. ISSN 2365-6549. doi:10.1002/slct.201901879.
^ Ma, Le-Le; Liu, Ming-Xuan; Liu, Xu-Ying; Sun, Wan; Lu, Zhong-Lin; Gao, Yong-Guang; He, Lan. Macrocyclic polyamine [12]aneN3 modified triphenylamine-pyrazine derivatives as efficient non-viral gene vectors with AIE and two-photon imaging properties. Journal of Materials Chemistry B. 2020, 8 (17): 3869–3879. ISSN 2050-750X. doi:10.1039/D0TB00321B.
^ Kumar, Bijari Anil; Nayak, Rati Ranjan. Supramolecular phenoxy-alkyl maleate-based hydrogels and their enzyme/pH-responsive curcumin release. New Journal of Chemistry. 2019, 43 (14): 5559–5567. ISSN 1144-0546. doi:10.1039/C8NJ05796F.
^ Luo, Li; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong. Design, synthesis and evaluation of phthalide alkyl tertiary amine derivatives as promising acetylcholinesterase inhibitors with high potency and selectivity against Alzheimer's disease. Bioorganic & Medicinal Chemistry. 2020, 28 (8): 115400. ISSN 0968-0896. doi:10.1016/j.bmc.2020.115400.
^ Zhao, Xuan; Huang, Yuchao; Yuan, Gankun; Zuo, Ke; Huang, Yafan; Chen, Juanjuan; Li, Jinyu; Xue, Jinping. A novel tumor and mitochondria dual-targeted photosensitizer showing ultra-efficient photodynamic anticancer activities. Chemical Communications. 2019, 55 (6): 866–869. ISSN 1359-7345. doi:10.1039/C8CC09456J.
^ Verma, Piyush Kumar; Prasad, K. Sujit; Varghese, Dominic; Geetharani, K. Cobalt(I)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides. Organic Letters. 2020, 22 (4): 1431–1436. ISSN 1523-7060. doi:10.1021/acs.orglett.0c00038.
^ Iwasaki, Tomoya; Tajimi, Yuka; Kameda, Kenta; Kingwell, Callum; Wcislo, William; Osaka, Kazuyuki; Yamawaki, Mugen; Morita, Toshio; Yoshimi, Yasuharu. Synthesis of 23-, 25-, 27-, and 29-Membered (Z)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization. The Journal of Organic Chemistry. 2019, 84 (12): 8019–8026. ISSN 0022-3263. doi:10.1021/acs.joc.9b00870.
^ Yang, Bo; Lu, Zhan. Visible-Light-Promoted Oxidative [4 + 2] Cycloadditions of Aryl Silyl Enol Ethers. The Journal of Organic Chemistry. 2016, 81 (16): 7288–7300. ISSN 0022-3263. doi:10.1021/acs.joc.6b01016.

[1] Kurbanli, Kamuran; Ahmetli, Gulnare; Tarlan, Esra. Synthesis of biologically active and environmental friendly insect pesticides: pheromones. Asian Journal of Chemistry, 2009. 21 (3): 1903-1909. ISSN: 0970-7077.

[2] Degering, Ed. F.; Boatright, Leslie G. Studies on the Synthesis of Lysine1. Journal of the American Chemical Society. 1950, 72 (11): 5137–5139. ISSN 0002-7863. doi:10.1021/ja01167a091.

[OliveiraSouza2019-3] Oliveira, Adeildo Junior; Souza, Isis Torres; Bernardo, Vanderson Barbosa; Santos, Larissa C.; Lima, Maria Raquel Ferreira; Goulart, Henrique Fonseca; Goulart Santana, Antônio Euzébio. Monobromination of α, ω‐Diols: Highly Efficient Preparation of Synthetic Intermediates. ChemistrySelect. 2019, 4 (36): 10843–10845. ISSN 2365-6549. doi:10.1002/slct.201901879.

[4] Ma, Le-Le; Liu, Ming-Xuan; Liu, Xu-Ying; Sun, Wan; Lu, Zhong-Lin; Gao, Yong-Guang; He, Lan. Macrocyclic polyamine [12]aneN3 modified triphenylamine-pyrazine derivatives as efficient non-viral gene vectors with AIE and two-photon imaging properties. Journal of Materials Chemistry B. 2020, 8 (17): 3869–3879. ISSN 2050-750X. doi:10.1039/D0TB00321B.

[5] Kumar, Bijari Anil; Nayak, Rati Ranjan. Supramolecular phenoxy-alkyl maleate-based hydrogels and their enzyme/pH-responsive curcumin release. New Journal of Chemistry. 2019, 43 (14): 5559–5567. ISSN 1144-0546. doi:10.1039/C8NJ05796F.

[6] Luo, Li; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong. Design, synthesis and evaluation of phthalide alkyl tertiary amine derivatives as promising acetylcholinesterase inhibitors with high potency and selectivity against Alzheimer's disease. Bioorganic & Medicinal Chemistry. 2020, 28 (8): 115400. ISSN 0968-0896. doi:10.1016/j.bmc.2020.115400.

[7] Zhao, Xuan; Huang, Yuchao; Yuan, Gankun; Zuo, Ke; Huang, Yafan; Chen, Juanjuan; Li, Jinyu; Xue, Jinping. A novel tumor and mitochondria dual-targeted photosensitizer showing ultra-efficient photodynamic anticancer activities. Chemical Communications. 2019, 55 (6): 866–869. ISSN 1359-7345. doi:10.1039/C8CC09456J.

[8] Verma, Piyush Kumar; Prasad, K. Sujit; Varghese, Dominic; Geetharani, K. Cobalt(I)-Catalyzed Borylation of Unactivated Alkyl Bromides and Chlorides. Organic Letters. 2020, 22 (4): 1431–1436. ISSN 1523-7060. doi:10.1021/acs.orglett.0c00038.

[9] Iwasaki, Tomoya; Tajimi, Yuka; Kameda, Kenta; Kingwell, Callum; Wcislo, William; Osaka, Kazuyuki; Yamawaki, Mugen; Morita, Toshio; Yoshimi, Yasuharu. Synthesis of 23-, 25-, 27-, and 29-Membered (Z)-Selective Unsaturated and Saturated Macrocyclic Lactones from 16- and 17-Membered Macrocyclic Lactones and Bromoalcohols by Wittig Reaction, Yamaguchi Macrolactonization, and Photoinduced Decarboxylative Radical Macrolactonization. The Journal of Organic Chemistry. 2019, 84 (12): 8019–8026. ISSN 0022-3263. doi:10.1021/acs.joc.9b00870.

[10] Yang, Bo; Lu, Zhan. Visible-Light-Promoted Oxidative [4 + 2] Cycloadditions of Aryl Silyl Enol Ethers. The Journal of Organic Chemistry. 2016, 81 (16): 7288–7300. ISSN 0022-3263. doi:10.1021/acs.joc.6b01016.

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