2-ethoxy-2-phenylethyl bromide | 6589-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-ethoxy-2-phenylethyl bromide
• 英文别名: 1-phenyl-1-ethoxy-2-bromoethane；2-bromo-1-ethoxy-1-phenylethane；(2-bromo-1-ethoxyethyl)benzene；ethyl-(2-bromo-1-phenyl-ethyl)-ether；Aethyl-(2-brom-1-phenyl-aethyl)-aether
• CAS: 6589-30-6
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: YHUCDZJCFPRKAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethoxy-2-phenylethyl bromide 在 氢氧化钾 作用下， 生成 1-乙氧基乙烯基苯
  参考文献：
  名称：

  Lauer; Spielman, Journal of the American Chemical Society, 1931, vol. 53, p. 1535

  摘要：

  DOI：
• 作为产物：
  描述：

  [acetyloxy-(2-ethoxy-2-phenylethyl)thallanyl] acetate 在 potassium bromide 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 生成 2-ethoxy-2-phenylethyl bromide
  参考文献：
  名称：

  烯烃烷氧基铊(III)化合物的合成及其与铜卤化物和伪卤化物的反应

  摘要：

  一些新的烯烃烷氧基铊(III)化合物，C6H5C(R1)(OR3)CH2Tl(OCOR2)2 [I]，是由苯乙烯和α-甲基苯乙烯与乙酸铊(III)和异丁酸在各种醇中制备的。I(R1=H) 与碘化铜、溴化铜、氯化铜、氰化物和硫氰酸铜反应生成相应的烷基卤化物和拟卤化物，C6H5CH(OR3)CH2X[II]，在各种有机溶剂中，乙腈是首选溶剂为了准备II。钾盐的加入对提高Ⅱ的收率有显着效果。卤代和假卤代脱卤发生在铊先前与烷基碳相连的位置。提出了一种离子协调的分子间方案作为制备 II 的反应机制。简要讨论了 I 的核磁共振和红外光谱数据。

  DOI：

  10.1246/bcsj.47.920

文献信息

• Mild and Efficient Vicinal Dibromination of Olefins Mediated by Aqueous Ammonium Fluoride
  作者：Tony Shing、Ying-Yeung Yeung、Wing Ng

  DOI：10.1055/s-0036-1588506

  日期：2018.3

  A mild and efficient vicinal dibromination of olefins has been developed by using saturated aqueous ammonium fluoride solution as the promoter. Inexpensive and commercially available N -bromosuccinimide (NBS) was used as the brominating reagent. The corresponding vicinal dibromoalkanes could be obtained in good to excellent yields.

  以饱和氟化铵水溶液为促进剂，开发了温和高效的烯烃邻位二溴化反应。使用廉价且可商购的 N-溴代琥珀酰亚胺 (NBS) 作为溴化试剂。可以以良好到极好的产率获得相应的邻位二溴烷烃。
• Electrochemical bromofunctionalization of alkenes in a flow reactor
  作者：Jakob Seitz、Thomas Wirth

  DOI：10.1039/d1ob01302e

  日期：——

  of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, the in situ generation of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted

  迄今为止，有机分子的溴化已得到广泛研究，但仍然需要安全和可持续的方法。有害试剂、选择性、低原子经济性和废物产生是溴化试剂最持久的问题。溴化物电化学氧化成溴是通过避免化学氧化剂减少废物的可行策略。此外，活性中间体的原位生成将危险试剂的风险降至最低。在这项工作中，我们研究了在流动电化学反应器中从氢溴酸电化学生成溴。各种烯烃可以以良好到极好的收率转化为其相应的二溴化物、溴醇、溴醇醚和环化产物。
• Halofunctionalization of alkenes by vanadium chloroperoxidase from Curvularia inaequalis
  作者：Jia Jia Dong、Elena Fernández-Fueyo、Jingbo Li、Zheng Guo、Rokus Renirie、Ron Wever、Frank Hollmann

  DOI：10.1039/c7cc03368k

  日期：——

  The vanadium-dependent chloroperoxidase from Curvularia inaequalis is a stable and efficient biocatalyst for the hydroxyhalogenation of a broad range of alkenes into halohydrins. Up to 1200000 TON with 69 s−1 TOF were observed for the biocatalyst. A bienzymatic cascade to yield epoxides as reaction products is presented.

  来自弯孢不动杆菌的钒依赖性氯过氧化物酶是一种稳定有效的生物催化剂，用于将多种烯烃羟基卤化为卤代醇。对于该生物催化剂，观察到高达1200万吨的TOS为69 s -1。提出了双酶级联反应以产生环氧化物作为反应产物。
• Potential antitussives: Synthesis and pharmacology of a series of 1-[2-amino-2-(4-fluorophenyl)ethyl]-4-(2-benzoylpropyl)piperazines
  作者：Zdeněk Vejdělek、Miroslav Protiva

  DOI：10.1135/cccc19832977

  日期：——

  Compound V, obtained by a reaction of 2-chloro-4'-fluoroacetophenone with 1-(ethoxycarbonyl)piperazine, was reduced with sodium borohydride to the amino alcohol VIf. The hydrochloride of VIf was treated with thionyl chloride to give the hydrochloride of 1-[2-chloro-2-(4-fluorophenyl)ethyl]-4-(ethoxycarbonyl)piperazine (VIg). The crude VIg was subjected to substitution reactions with diethylamine, pyrrolidine, piperidine, morpholine and 1-methylpiperazine in benzene at 60 °C. The obtained aminocarbamates VIa-VIe were hydrolyzed with concentrated ethanolic potassium hydroxide and gave the amines VIIa-VIIe. Mannich reactions of the hydrochlorides of these compounds with paraformaldehyde and propiophenone (and 4-hydroxypropiophenone, respectively) resulted in the title compounds IIIa-IIIe, IVa,b and IVd,e. Only substances IIIa and IIId were found to have an antitussic activity in rats and guinea-pigs comparable to that of eprazinone (I). In higher doses they brought about central depression, ataxia and ptosis in mice and some of them adrenolytic and hypotensive effects in rats.

  通过将2-氯-4'-氟乙酰苯酮与1-(乙氧羰基)哌嗪反应得到化合物V，然后用硼氢化钠还原为氨基醇VIf。将VIf的盐酸盐与亚硫酰氯处理得到1-[2-氯-2-(4-氟苯基)乙基]-4-(乙氧羰基)哌嗪的盐酸盐（VIg）。粗制的VIg在苯中与二乙胺、吡咯烷、哌啶、吗啉和1-甲基哌嗪进行取代反应，产生氨基氨基甲酸酯VIa-VIe。用浓缩的乙醇钾氢氧化物水解VIa-VIe，得到胺类物质VIIa-VIIe。这些化合物的盐酸盐与多聚甲醛和丙酮苯酮（和对羟基丙酮苯酮，分别）进行Mannich反应，得到标题化合物IIIa-IIIe、IVa,b和IVd,e。只有IIIa和IIId这两种物质在大鼠和豚鼠中显示出与依普拉津酮（I）相当的止咳活性。在较高剂量下，它们会导致小鼠出现中枢抑制、共济失调和上睑下垂，部分物质在大鼠中还表现出肾上腺素拮抗和降压作用。
• Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers
  作者：Oleg V. Bityukov、Vera A. Vil'、Gennady I. Nikishin、Alexander O. Terent'ev

  DOI：10.1002/adsc.202100161

  日期：2021.6.21

  Bromohydrins and their ethers were electrochemically synthesized via hydroxy- and alkoxybromination of alkenes using potassium bromide and water or alcohols. High selectivity of bromohydrins formation was achieved only with the use of DMSO as the solvent and an acid as the additive. The proposed combination of starting reagents, additives, and solvents allowed to form bromohydrins or their ethers selectively

  溴醇及其醚是通过使用溴化钾和水或醇的烯烃的羟基和烷氧基溴化而电化学合成的。只有使用 DMSO 作为溶剂和酸作为添加剂才能实现溴醇形成的高选择性。尽管有多种副产物（环氧化物、二溴化物、二醇），所提议的起始试剂、添加剂和溶剂的组合允许选择性地形成溴醇或其醚。溴醇以高产率获得，高达 96%，在配备玻璃碳和高电流密度铂电极的未分割电化学电池中具有广泛的底物范围。