1-(4-bromophenyl)-2-(1,3-dioxolan-2-yl)ethanone | 117372-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-bromophenyl)-2-(1,3-dioxolan-2-yl)ethanone
• 英文别名: 1-(4-bromo-phenyl)-2-[1,3]dioxolan-2-yl-ethanone；1-(4-Brom-phenyl)-2-[1,3]dioxolan-2-yl-aethanon；1-(4-Bromophenyl)-2-(1,3-dioxolan-2-yl)ethanone
• CAS: 117372-49-3
• 化学式: C₁₁H₁₁BrO₃
• 分子量: 271.111
• InChiKey: SEYZZJSEGGRCRG-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C
• 沸点：
  372.5±27.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-4'-溴-beta-氯丙烯酰苯 在 氢氧化钾 、 乙二醇 作用下， 生成 1-(4-bromophenyl)-2-(1,3-dioxolan-2-yl)ethanone
  参考文献：
  名称：

  Kotschetkow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2570,2573; engl. Ausg. S. 2533, 2536

  摘要：

  DOI：

文献信息

• Visible-Light-Driven Denitrogenative C–C Bond Formation and Oxidative Difunctionalization of Vinyl Azides
  作者：Adinath Majee、Santosh Sing Sardar、Aramita De、Satyajit Pal、Subhankar Sarkar、Sougata Santra、Grigory V. Zyryanov

  DOI：10.1055/a-2131-3208

  日期：2024.2

  A newer synthetic protocol has been developed to synthesize α-oxyalkyl ketones from vinyl azides under transition-metal-free reaction conditions. The reaction proceeds in the presence of organic photoredox catalyst rose bengal, an oxidant tert-butyl hydroperoxide (TBHP), and ethers. A broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, which readily

  开发了一种新的合成方案，可以在无过渡金属的反应条件下从乙烯基叠氮化物合成 α-氧基烷基酮。该反应在有机光氧化还原催化剂玫瑰红（一种氧化剂叔胺）的存在下进行-丁基氢过氧化物（TBHP）和醚。人们发现多种取代的乙烯基叠氮化物在可见光照射下可以顺利反应，这很容易提供相关产品。已经进行了一些对照实验来提出可能的机制。该过程由乙烯基叠氮化物的自由基加成引发，这触发了由二氮损失驱动的级联断裂机制，稳定的醚自由基最终产生α-氧基烷基酮。该方法提供了一种简单、温和、直接、新颖的制备α-烷氧基酮的范例。
• Regioselective Oxyalkylation of Vinylarenes Catalyzed by Diatomite-Supported Manganese Oxide Nanoparticles
  作者：Huayin Sun、Yonghui Zhang、Fengfeng Guo、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/jo2026367

  日期：2012.4.6

  A regioselective oxyalkylation reaction of vinylarenes with cyclic ethers was developed under the catalysis of a new heterogeneous catalyst, the diatomite-supported Mn3O4 nanoparticles (SMONP-1). The use of this heterogeneous catalyst provided a novel approach for the synthesis of alpha-carbonyled beta-alkylated aryl derivatives via a sp(3) C-H bond functionalization under mild aerobic conditions.
• CuBr-Mediated Oxyalkylation of Vinylarenes under Aerobic Conditions via Cleavage of sp³ C−H Bonds α to Oxygen
  作者：Kai Cheng、Lehao Huang、Yuhong Zhang

  DOI：10.1021/ol900947d

  日期：2009.7.2

  A novel difunctionalization reaction of vinylarenes with cyclic ethers has been developed by copper catalysis via direct activation of alpha-sp(3) C-H bonds of oxygen in the presence of 1-1.2 equiv of TBHP under mild aerobic conditions. The reaction shows excellent regioselectivities and good functional group tolerance to give the oxyalkylated products of vinylarenes.