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10-溴-1-癸醇

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10-溴-1-癸醇
英文名 10-Bromo-1-decanol
别名 10-溴癸醇
10-溴正癸醇
识别
CAS号 53463-68-6  checkY
SMILES
 
  • OCCCCCCCCCCBr
性质
化学式 C10H21BrO
摩尔质量 237.18 g·mol⁻¹
密度 1.160±0.06 g·cm−3（20 °C）[1]
沸点 166—169 °C（439—442 K）（10 Torr）[2]
溶解性（水） 0.038 g[1]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

10-溴-1-癸醇是一种有机化合物，化学式为C10H21BrO。

制备

10-溴-1-癸醇可由1,10-癸二醇和氢溴酸回流反应得到，[3]反应多用甲苯及水作为溶剂。[4]

硫酸-溴化钠虽然可以代替氢溴酸进行上述反应，但是会生成较多的1,10-二溴癸烷副产物。[5]

此外，溴化锂在3-戊酮中可将10-氯-1-癸醇转化为10-溴-1-癸醇。[6]

反应

10-溴-1-癸醇具有卤代烃和醇的通性。它在二氯甲烷中可以被氯铬酸吡啶鎓氧化为10-溴-1-癸醛。[7]它和二甲基叔丁基氯硅烷在咪唑的存在下于N,N-二甲基甲酰胺中反应，可以得到10-溴癸氧基叔丁基二甲基硅烷。[8]

10-溴-1-癸醇和碘化钠在丙酮中回流，发生卤素交换反应，生成10-碘-1-癸醇。[9]它和叠氮化钠在四丁基硫酸氢铵的催化下在水-四氢呋喃中反应，可以得到10-叠氮基-1-癸醇。[10]它和乙炔钠在N,N-二甲基甲酰胺中反应，得到11-十二炔-1-醇。[11]它和胺类反应，生成季铵盐，如和三正丙胺（德语：Tripropylamin）反应，生成10-羟癸基三丙基溴化铵。[12]

参考文献

  1. ^ 1.0 1.1 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-08-09]
  2. ^ Pattison, F. L. M.; Stothers, J. B.; Woolford, R. G. Anodic Syntheses Involving ι-Monohalocarboxylic Acids1. Journal of the American Chemical Society. 1956, 78 (10): 2255–2259. ISSN 0002-7863. doi:10.1021/ja01591a062. 
  3. ^ Karabiyikoglu, Sedef; Iafe, Robert G.; Merlic, Craig A. Ring-Closing Metathesis with Vicinal Dibromoalkenes as Protected Alkynes: A Synthetic Approach to Macrocyclic Enynes. Organic Letters. 2015, 17 (21): 5248–5251. ISSN 1523-7060. doi:10.1021/acs.orglett.5b02595. 
  4. ^ Põhako-Esko, Kaija; Taaber, Triinu; Saal, Kristjan; Lõhmus, Rünno; Kink, Ilmar; Mäeorg, Uno. New Method for Synthesis of Methacrylate-Type Polymerizable Ionic Liquids. Synthetic Communications. 2013, 43 (21): 2846–2852. ISSN 0039-7911. doi:10.1080/00397911.2012.745159. 
  5. ^ Majetich, G.; Hicks, R. Applications of microwave accelerated organic chemistry. Research on Chemical Intermediates. 1994, 20 (1): 61–77. ISSN 0922-6168. doi:10.1163/156856794X00072. 
  6. ^ Li, X.; Singh, S. M.; Labrie, F. A Convenient and Practical Method for Conversion of Primary Alkyl Chlorides to Highly Pure Bromides (≥99%). Synthetic Communications. 1994, 24 (5): 733–743. ISSN 0039-7911. doi:10.1080/00397919408012653. 
  7. ^ Furber, Mark; Taylor, Richard J. K.; Burford, S. Cliff. Stereospecific diene synthesis using acetylene carbocupration. Preparation of navel orangeworm pheromone and leukotriene analogs. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986. 10: 1809-1815. CODEN: JCPRB4. ISSN: 0300-922X.
  8. ^ Berube, Marie; Laplante, Yannick; Poirier, Donald. Design, Synthesis and In Vitro Evaluation of 4-Androstene-3,17-dione/Adenosine Hybrid Compounds as Bisubstrate Inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase. Medicinal Chemistry. 2006, 2 (4): 329–347. ISSN 1573-4064. doi:10.2174/157340606777724086. 
  9. ^ Berube, Marie; Laplante, Yannick; Poirier, Donald. Design, Synthesis and In Vitro Evaluation of 4-Androstene-3,17-dione/Adenosine Hybrid Compounds as Bisubstrate Inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase. Medicinal Chemistry. 2006, 2 (4): 329–347. ISSN 1573-4064. doi:10.2174/157340606777724086. 
  10. ^ Heimgartner, Heinz; P. Fritschi, Stephan; Linden, Anthony. Synthesis of Macrocyclic Lactams from 2-(ω-Aminoalkyl)-2-benzoylamino-3-phenyl-N,N-dimethylpropanamides via Direct Amide Cyclization. HETEROCYCLES. 2009, 79 (1): 985. ISSN 0385-5414. doi:10.3987/COM-08-S(D)76. 
  11. ^ Fedenok, L. G.; Plashchenyuk, E. V.; Myasnikova, R. N.; Shvartsberg, M. S. Synthesis of long-chain 2-alkadiynylpyridines. Izvestiya Akademii Nauk, Seriya Khimicheskaya, 1996. 3: 706-709. CODEN: IASKEA.
  12. ^ Jaeger, David A.; Zeng, Xiaohui; Apkarian, Robert P. Shamrock Surfactants: Synthesis and Characterization. Langmuir. 2004, 20 (24): 10427–10432. ISSN 0743-7463. doi:10.1021/la0481391. 
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