(3E)-4-phenyl-3-butenoic hydroxamic acid | 114142-28-8

• 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: (3E)-4-phenyl-3-butenoic hydroxamic acid
• 英文别名: trans-N-hydroxy-4-phenylbut-3-enamide；(3E)-N-hydroxy-4-phenylbut-3-enamide；(E)-N-hydroxy-4-phenylbut-3-enamide；Cinnamyl hydroxamic acid
• CAS: 114142-28-8
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: PJEPLMBYFDATIS-QPJJXVBHSA-N

物化性质

• 熔点：
  135-137 °C
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E)-4-phenyl-3-butenoic hydroxamic acid 在 溴 作用下， 生成 benzyl (3-bromo-5-oxo-2-phenylpyrrolidin-1-yl) carbonate
  参考文献：
  名称：

  γ-substituent effects on the oxidative cyclization of o-acyl β,γ-unsaturated hydroxamates

  摘要：

  DOI：

  10.1016/s0040-4039(01)91346-2
• 作为产物：
  描述：

  反-苯乙烯乙酸 在 草酰氯 、 盐酸羟胺 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (3E)-4-phenyl-3-butenoic hydroxamic acid
  参考文献：
  名称：

  通过 π 受体酞菁配体实现的铁催化烯烃氧酰胺化获得 β-内酰胺

  摘要：

  在此，我们报告了利用束缚二恶唑酮作为类氮芥前体来生产有价值的β-内酰胺支架的铁催化烯烃酰胺化的发展。机理研究表明，酞菁配体相对较强的 π 接受能力对于生成关键的三重态铁-亚胺基自由基中间体至关重要，从而能够以高非对映选择性结合氧亲核试剂进行4-外-三内酰胺化。这种环化方法很容易扩展到高效的 γ-内酰胺合成（TON > 300）。

  DOI：

  10.1021/jacs.1c12125

文献信息

• New Preparation of (<i>Z</i>)-1-Phenyl-3-cyano-2-propen-1-ones
  作者：Houssam Trabulsi、Gérard Rousseau

  DOI：10.1080/00397911.2010.497598

  日期：2011.7.15

  Abstract Reaction of γ-phenyl-β,γ-unsaturated hydroxamates with bis(collidine)bromine(I) hexafluorophosphate led to the formation of cyclic bromo imidates. Reaction of these with triethylamine led to the formation of 3-cyano-2-propen-1-ones with good yields by a fragmentation reaction.

  摘要 γ-苯基-β,γ-不饱和异羟肟酸酯与双（可力丁）溴（I）六氟磷酸酯反应生成环状溴亚胺酸酯。这些与三乙胺的反应导致通过裂解反应以良好的产率形成 3-cyano-2-propen-1-ones。
• Tethered Aminohydroxylation (TA) Reaction of Amides
  作者：Timothy J. Donohoe、Cedric K. A. Callens、Amber L. Thompson

  DOI：10.1021/ol900631y

  日期：2009.6.4

  The first examples of amide-tethered aminohydroxylation reactions, catalyzed by osmium, showing that the use of N−O-based reoxidants are essential for success, are reported. The system that is described is compatible with a variety of different alkene substitution patterns and ring sizes and works with low loadings in both cyclic and acyclic systems. The levels of diastereoselectivity that were observed

  据报道，催化的酰胺束缚的氨基羟基化反应的第一个例子表明，使用基于N-O的再氧化剂对成功至关重要。所描述的系统与多种不同的烯烃取代方式和环大小兼容，并且在环状和非环状系统中均以低负荷运行。对于在有机合成中使用立体选择性TA反应而言，对于在烯丙基和烯丙基位置上的取代基都观察到的非对映选择性水平很好。
• Preparation of Imino Lactones by Electrophilic Cyclization of β,γ-Unsaturated Hydroxamates: Formation of 3-Cyanoprop-2-en-1-ones through Fragmentation Reactions
  作者：Houssam Trabulsi、Régis Guillot、Gérard Rousseau

  DOI：10.1002/ejoc.201000376

  日期：2010.10

  Treatment of γ-disubstituted β,γ-unsaturated hydroxamates with bis(collidine)bromine(I) hexafluorophosphate led mainly to the formation of cyclic bromo imidates - the thermodynamic products. Unsaturated cyclic imidates were then obtained by treatment with triethylamine. With γ-aryl β,γ-unsaturated hydroxamates, the corresponding cyclic bromo imidates were also obtained. On treatment with triethylamine

  用双（可力丁）溴（I）六氟磷酸酯处理 γ-二取代的 β,γ-不饱和异羟肟酸酯主要导致环状溴亚胺酸酯（热力学产物）的形成。然后通过用三乙胺处理获得不饱和环状亚胺酸酯。用γ-芳基β,γ-不饱和异羟肟酸酯，也得到了相应的环状溴亚胺酸酯。然而，在用三乙胺处理时，这些化合物通过裂解反应以良好的产率形成 3-cyanoprop-2-en-1-ones。
• N-hydroxy γ-lactams or cyclic N-hydroxy imidates from the organoselenium-induced cyclization of β,γ-unsaturated hydroxamic acids
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Francesca Marini

  DOI：10.1039/c39940000221

  日期：——

  The organoselenium-induced ring-closure reactions of γ-substituted β, γ-unsaturated hydroxamic acids afforded cyclic phenylseleno N-hydroxy imidates or phenylseleno N-hydroxy γ-lactams as the kinetically or thermodynamically controlled products, respectively.

  有机硒诱导的γ-取代的β、γ-不饱和异羟肟酸的闭环反应分别提供环状苯基硒基N-羟基亚氨酸盐或苯基硒基N-羟基γ-内酰胺作为动力学或热力学控制的产物。
• A sulfur-containing diselenide as an efficient chiral reagent in asymmetric selenocyclization reactions
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Luana Bagnoli、Claudio Santi、Andrea Temperini

  DOI：10.1016/s0957-4166(01)00248-8

  日期：2001.6

  Treatment of the di-2-[(IS)-1-(methylthio)ethyl]phenyl diselenide with bromine and silver triflate afforded the corresponding selenyl triflate which was used in situ as a strongly electrophilic selenium reagent to effect the asymmetric synthesis of oxygen- or nitrogen-containing heterocycles. Cyclic ethers, lactones, lactams or N-protected pyrrolidines have been prepared in good yield with complete regioselectivity and high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.