3,4-dihydroxy-1-phenyl-1-butanone | 86542-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydroxy-1-phenyl-1-butanone
• 英文别名: 3,4-dihydroxy-1-phenylbutan-1-one；(rac)-3,4-dihydroxy-1-phenylbutan-1-one
• CAS: 86542-12-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: XXHBLDVZBROWQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-phenylbut-3-en-1-one oxime 在 甲醇 、 水 、 铁粉 、 氯化铵 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 36.0h， 生成 3,4-dihydroxy-1-phenyl-1-butanone
  参考文献：
  名称：

  肟激进晋升双加氧，Oxyamination，和烯的Diamination：异恶唑啉和循环硝酮的合成

  摘要：

  出速度：分子内除了肟基团到CC键的通过使用DEAD和TEMPO，得到4,5- dihydroisoxazoles作为结果实现一个C  O键形成，5-外-trig环化。γ，δ不饱和酮肟也反应至C，得到环状硝酮 N键的形成。这些反应为未活化烯烃的邻位双官能化提供了一种无金属的方法。

  DOI：

  10.1002/anie.201203799

文献信息

• Oxime Radical Promoted Dioxygenation, Oxyamination, and Diamination of Alkenes: Synthesis of Isoxazolines and Cyclic Nitrones
  作者：Bing Han、Xiu-Long Yang、Ran Fang、Wei Yu、Chao Wang、Xiao-Yong Duan、Shuai Liu

  DOI：10.1002/anie.201203799

  日期：2012.8.27

  Up the tempo: The intramolecular addition of oxime radicals to CC bonds was achieved by using DEAD and TEMPO to give 4,5‐dihydroisoxazoles as a result of a CO bond‐forming, 5‐exo‐trig cyclization. γ,δ‐Unsaturated ketoximes also reacted to afford cyclic nitrones through CN bond formation. The reactions offer a metal‐free approach for the vicinal difunctionalization of unactivated alkenes.

  出速度：分子内除了肟基团到CC键的通过使用DEAD和TEMPO，得到4,5- dihydroisoxazoles作为结果实现一个C  O键形成，5-外-trig环化。γ，δ不饱和酮肟也反应至C，得到环状硝酮 N键的形成。这些反应为未活化烯烃的邻位双官能化提供了一种无金属的方法。
• Reduction of .DELTA.2-isoxazolines. 3. Raney nickel catalyzed formation of .beta.-hydroxy ketones
  作者：Dennis P. Curran

  DOI：10.1021/ja00356a021

  日期：1983.9

  On determine les conditions optimales de transformation d'isoxazolines-2 en β-hydroxycetones en utilisant un catalyseur Ni de Raney, l'acide borique, un melange 5/1 methanol/eau et l'hydrogene gazeux

  确定最佳条件转化 d'isoxazolines-2 en β-hydroxycetones en utilisant un catalyseur Ni de Raney, l'acide borique, un melange 5/1 甲醇/eau et l'hydrogene Gazeux
• Chloramphenicol base chemistry. Part 10 1 : Asymmetric synthesis of α -hydroxy chiral alcohols via intramolecular Michael additions of γ -hydroxy- α , β -unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts
  作者：Haifeng Wang、Linjie Yan、Yan Wu、Fener Chen

  DOI：10.1016/j.tet.2017.03.076

  日期：2017.5

  γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE

  我们已经开发了氯霉素碱脲催化的γ-羟基-α，β-不饱和烯酮的分子内迈克尔加成。所得产物的氧化提供了以良好的效率和对映选择性容易地获得相应的α-羟基手性醇的反应，该反应显示出广泛的底物范围。通过合成（R）-2-羟基-4-苯基丁酸（R）-2-羟基-4-苯基丁酸酯进一步证明了该方法的实用性，这是构建ACE抑制剂盐酸贝那普利的关键组成部分。
• WATER-BASED EXTRUSION PRIMER FOR POLYETHYLENE
  申请人：Henkel AG & Co. KGaA

  公开号：EP3699247A1

  公开（公告）日：2020-08-26

  The invention relates to a specific method of manufacturing a multilayer laminate. Additionally, the invention is directed to a multilayer laminate obtained by the method according to the invention and to the use of a specific aqueous coating composition comprising at least one specific copolymer as extrusion primer.

  本发明涉及一种制造多层层压板的特殊方法。此外，本发明还涉及一种通过本发明方法获得的多层层压板，以及使用一种包含至少一种特定共聚物的特定水性涂料组合物作为挤出底漆。
• Enantioselective, Organocatalytic Oxy-Michael Addition to γ/δ-Hydroxy-α,β-enones:  Boronate-Amine Complexes as Chiral Hydroxide Synthons
  作者：De Run Li、Andiappan Murugan、J. R. Falck

  DOI：10.1021/ja076802c

  日期：2008.1.1

  An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.