2-(2-乙酰基苯氧基)-1-溴乙烷 | 52191-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(2-乙酰基苯氧基)-1-溴乙烷
• 英文名称: 2-(2-acetylphenoxy)-1-bromoethane
• 英文别名: 2'-(2-bromoethoxy)acetophenone；2-(2-bromoethoxy)acetophenone；1-[2-(2-Bromoethoxy)phenyl]ethan-1-one；1-[2-(2-bromoethoxy)phenyl]ethanone
• CAS: 52191-14-7
• 化学式: C₁₀H₁₁BrO₂
• mdl: MFCD04635887
• 分子量: 243.1
• InChiKey: BDCJLOGWIWITNO-UHFFFAOYSA-N

物化性质

• 熔点：
  43 °C
• 沸点：
  315.1±22.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-乙酰基苯氧基)-1-溴乙烷 在 sodium hydride 、 三氯氧磷 作用下， 生成 5-chloro-2,3-dihydro-1-benzoxepin-4-carboxaldehyde
  参考文献：
  名称：

  Structure-based design of thienobenzoxepin inhibitors of PI3-kinase

  摘要：

  Starting from thienobenzopyran HTS hit 1, co-crystallization, molecular modeling and metabolic analysis were used to design potent and metabolically stable inhibitors of PI3-kinase. Compound 15 demonstrated PI3K pathway suppression in a mouse MCF7 xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.124
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 1,2-二溴乙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以60%的产率得到2-(2-乙酰基苯氧基)-1-溴乙烷
  参考文献：
  名称：

  基于 McMurry 耦合的几何纯对称和不对称羟基芪的有效合成策略

  摘要：

  使用低价钛 (LVT) 试剂 (TiCl 4 -Zn-THF) 对乙烯-二氧基束缚的对称和不对称芳族双（羰基）醚进行分子内还原脱氧，得到相应环状二苯乙烯的可色谱分离的 E/Z 异构体，进一步得到脱烷基化以获得几何纯的羟基芪。另一方面，束缚双（羰基）醚与 TiCl 3 -Li-THF 的分子内 McMurry 偶联通过苯酚官能团的原位脱烷氧基化直接提供对称和不对称菲。这是通过LVT路线合成不对称菲的第一份报告。

  DOI：

  10.1055/s-2003-41004

文献信息

• Microwave-assisted synthesis of 1,3-dialkyl ethers of calix[4]arenes: application to the synthesis of cesium selective calix[4]crown-6 ionophores
  作者：Sandip K. Nayak、Manoj K. Choudhary

  DOI：10.1016/j.tetlet.2011.10.142

  日期：2012.1

  phenolic-OH groups of calix[4]arenes with various alkyl halides/tosylates and K2CO3 under microwave irradiation afforded 1,3-dialkoxycalix[4]arenes in their cone conformation only as predominant/sole product in good yields (71–85%). The protocol was found to be much superior to conventional heating both in terms of yield and reaction time. Some of the 1,3-dialkoxycalix[4]arenes were elaborated further

  微波辐射下杯[4]芳烃的苯酚-OH基与各种烷基卤化物/甲苯磺酸酯和K 2 CO 3的部分醚化，仅以主要/单一产物的形式提供1,3-二烷氧基杯[4]芳烃，其圆锥构象仅为高收率（71–85％）。发现该方案在产率和反应时间方面均比常规加热好得多。一些1,3-二烷氧基杯[4]芳烃被进一步精制为铯选择性杯[4]冠6离子载体的合成。
• Cyclization of 2-(2-bromoethoxy)-acetophenones and 5-(ω-haloalkoxy)-1,5-dihydro-2<i>H</i>-pyrrol-2-ones – Formation of five- to eight-membered oxygen-containing heterocycles via intramolecular alkylation
  作者：Kirill V Nikitin、Nonna P Andryukhova

  DOI：10.1139/v04-011

  日期：2004.5.1

  Under basic conditions (lithium diisopropylamide or sodium hydride in THF) 2-(2-bromoethoxy)-acetophenones were transformed to 3,4-dihydro[1]benzoxepin-5(2H)-ones (homochromanones) in high yields. ...

  在碱性条件下（THF 中的二异丙基氨基锂或氢化钠），2-(2-溴乙氧基)-苯乙酮以高产率转化为 3,4-二氢[1] 苯并氧杂-5(2H)-酮（高色满酮）。...
• Sodium Bromide-Catalyzed Oxidation of Secondary Benzylic Alcohols Using Aqueous Hydrogen Peroxide as Terminal Oxidant
  作者：Takashi Nagano、Hiromi Komagawa、Yukako Maejima

  DOI：10.1055/s-0035-1560549

  日期：——

  A halide salt, hydroperoxide and AcOH catalyst system was applied to the oxidation of secondary benzylic alcohols. This simple system can be applied to a variety of secondary benzylic alcohols and scaled up for gram-scale preparation. High secondary benzylic alcohol selectivity of the present method is demonstrated in hydroxyketone synthesis. Based on several experimental results, a catalytic cycle for our oxidation is proposed.
• An Efficient Synthetic Strategy for Geometrically Pure Symmetrical and Unsymmetrical Hydroxystilbenes via McMurry Coupling
  作者：Subrata Chattopadhyay、Narayan V. Mayekar、Sandip K. Nayak

  DOI：10.1055/s-2003-41004

  日期：——

  Intramolecular reductive deoxygenation of ethylene-dioxy tethered symmetrical and unsymmetrical aromatic bis(carbonyl) ethers with the low-valent titanium (LVT) reagent (TiCl 4 -Zn-THF) yielded chromatographically separable E/Z-isomers of corresponding cyclic stilbenes which were further dealkylated to obtain geometrically pure hydroxystilbenes. The intramolecular McMurry coupling of the tethered bis(carbonyl)

  使用低价钛 (LVT) 试剂 (TiCl 4 -Zn-THF) 对乙烯-二氧基束缚的对称和不对称芳族双（羰基）醚进行分子内还原脱氧，得到相应环状二苯乙烯的可色谱分离的 E/Z 异构体，进一步得到脱烷基化以获得几何纯的羟基芪。另一方面，束缚双（羰基）醚与 TiCl 3 -Li-THF 的分子内 McMurry 偶联通过苯酚官能团的原位脱烷氧基化直接提供对称和不对称菲。这是通过LVT路线合成不对称菲的第一份报告。
• Structure-based design of thienobenzoxepin inhibitors of PI3-kinase
  作者：Steven T. Staben、Michael Siu、Richard Goldsmith、Alan G. Olivero、Steven Do、Daniel J. Burdick、Timothy P. Heffron、Jenna Dotson、Daniel P. Sutherlin、Bing-Yan Zhu、Vickie Tsui、Hoa Le、Leslie Lee、John Lesnick、Cristina Lewis、Jeremy M. Murray、Jim Nonomiya、Jodie Pang、Wei Wei Prior、Laurent Salphati、Lionel Rouge、Deepak Sampath、Steve Sideris、Christian Wiesmann、Ping Wu

  DOI：10.1016/j.bmcl.2011.04.124

  日期：2011.7

  Starting from thienobenzopyran HTS hit 1, co-crystallization, molecular modeling and metabolic analysis were used to design potent and metabolically stable inhibitors of PI3-kinase. Compound 15 demonstrated PI3K pathway suppression in a mouse MCF7 xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.