1-(3,5-dibromo-phenyl)-but-3-en-1-ol | 865307-59-1

• 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: 1-(3,5-dibromo-phenyl)-but-3-en-1-ol
• 英文别名: 1-(3,5-Dibromophenyl)but-3-en-1-ol
• CAS: 865307-59-1
• 化学式: C₁₀H₁₀Br₂O
• 分子量: 305.997
• InChiKey: MLCCHMRFGDGYCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,5-dibromo-phenyl)-but-3-en-1-ol 在 Jones reagent 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 1-(3,5-Dibromophenyl)but-3-en-1-one
  参考文献：
  名称：

  分子氧与烯基肟的无金属自氧化硝基氧化

  摘要：

  描述了由亚硝酸叔丁酯介导的烯基肟的无金属好氧自氧化硝基氧化。分子氧用作氧化剂，避免使用有机捕集剂，例如2,2,6,6-四甲基哌啶1-氧基（TEMPO）。所需产物通常以高收率获得。

  DOI：

  10.1002/adsc.201600147
• 作为产物：
  描述：

  烯丙基三甲氧基硅烷 、 3,5-二溴苯甲醛 在 邻苯二酚 、 三乙胺 作用下， 反应 24.0h， 以84%的产率得到1-(3,5-dibromo-phenyl)-but-3-en-1-ol
  参考文献：
  名称：

  Phenylene Alkylene Dendrons with Site-Specific Incorporated Fluorescent Pyrene Probes

  摘要：

  [GRAPHICS]This report deals with the synthesis and the spectroscopic properties of two second generation (G2) dendrons with site-specific incorporated phenyl pyrene derivatives as solvatochromic fluorescent probes. The generations that do not carry the probe are equipped with volume dummies, pyrene moieties that do not show a solvatochromic effect. Two complementary G2 phenylene alkylene dendrons were synthesized using Suzuki-Miyaura cross coupling. Most of the reactions used in the 10-step sequence generating the target compounds proceeded in good yields. The incorporated probes can be selectively photoexcited and show solvatochromic shifts that are of the same magnitude as for the free probes in a homogeneous solvent environment. In addition to the chargetransfer fluorescence, a broad emission band is observed that is assigned to an intramolecular exciplex formation between the aryl pyrene chromophores.

  DOI：

  10.1021/jo050302p

文献信息

• Transition-metal-free oxychlorination of alkenyl oximes: in situ generated radicals with tert-butyl nitrite
  作者：Xiao-Wei Zhang、Zu-Feng Xiao、Mei-Mei Wang、Yan-Jun Zhuang、Yan-Biao Kang

  DOI：10.1039/c6ob01374k

  日期：——

  Oxychlorination of alkenyl oximes is harder compared to the analogous oxybromination or oxyiodination because of the difficulty associated with the formation of chlorine cations or radicals. A transition-metal-free oxychlorination of alkenyl oximes has been developed, using t-BuONO as a dual oxidant and AlCl3 as a chlorine source. This convenient and practical method has been used to construct chloroisoxazolines

  与类似的氧溴化或氧碘化相比，烯基肟的氧氯化更难，因为与形成氯阳离子或自由基有关的困难。已经开发出一种无过渡金属的烯基肟的氧氯化方法，该方法使用t -BuONO作为双氧化剂，并使用AlCl 3作为氯源。这种方便实用的方法已被用于以中等至良好的产率构建氯异恶唑啉，而N-氯代琥珀酰亚胺（NCS）未能促进该反应。
• Ruthenium-Catalyzed Direct Transformation of Alkenyl Oximes to 5-Cyanated Isoxazolines: A Cascade Approach Based on Non-Stabilized Radical Intermediate
  作者：Dan-Jun Wang、Bei-Yi Chen、Yi-Qi Wang、Xiao-Wei Zhang

  DOI：10.1002/ejoc.201701651

  日期：2018.3.22

  A convenient method offers an easy access to 5‐cyanated isoxazolines in good to high yields and shows good functional group tolerance and high efficiency. In this protocol, tert‐butyl nitrte plays a dual role, acting as an oxidant as well as a nitrogen source. Remarkably, this new reaction avoids using any toxic radical initiator or cyanide reagents and constructs C–O and C≡N triple bonds in a single‐step

  简便的方法可以轻松获得高产或高收率的5-氰化异恶唑啉，并显示出良好的官能团耐受性和高效率。在该协议中，硝酸叔丁酯起着双重作用，既充当氧化剂又充当氮源。值得注意的是，这种新反应避免了使用任何有毒的自由基引发剂或氰化物试剂，并且一步一步即可构建C–O和C≡N三键。