5-苯基-3-己烯-2-酮 | 60405-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-苯基-3-己烯-2-酮
• 英文名称: 5-phenyl-3-hexene-2-one
• 英文别名: 5-phenyl-hex-3-en-2-one；3-Hexen-2-one, 5-phenyl-；5-phenylhex-3-en-2-one
• CAS: 60405-50-7
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: ALFALFNFEGCXJO-UHFFFAOYSA-N

物化性质

• LogP：
  2.333 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-苯基-3-己烯-2-酮 在 copper(II) bis(trifluoromethanesulfonate) 、 三苯基膦 、 四甲基胍 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到
  参考文献：
  名称：

  铜催化不饱和化合物与空气的有氧氧化

  摘要：

  描述了一种温和且操作简单的铜催化乙烯基有氧氧化 β,γ-和 α,β-不饱和酯。该方法具有收率好、底物范围广、化学选择性和区域选择性好、官能团耐受性好等特点。该方法还能够氧化β,γ-和α,β-不饱和醛、酮、酰胺、腈和砜。此外，本催化体系适用于双乙烯基和三乙烯基氧化。发现四甲基胍 (TMG) 作为碱的作用至关重要，但我们也推测它可以作为三氟甲磺酸铜 (II) 的配体来生产活性铜​​ (II) 催化剂。进行的机械实验表明，通过烯丙基铜 (II) 物质存在一个合理的反应途径。最后，

  DOI：

  10.1021/jacs.8b01886
• 作为产物：
  描述：

  2-苯基丙醛 、 1-三苯基膦-2-丙酮 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 5-苯基-3-己烯-2-酮
  参考文献：
  名称：

  Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

  摘要：

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.039

文献信息

• Tandem hydroformylation/aldol condensation reactions: Synthesis of unsaturated ketones from olefins
  作者：László Kollár、Péter Pongrácz

  DOI：10.1016/j.jorganchem.2018.04.031

  日期：2018.7

  yields can be achieved with several ketones using styrene and α-methylstyrene as substrate in hydroformylation reaction. Linear aldehydes proved to be more active in aldol condensation step, furthermore, aromatic and cyclic ketones are also feasible coupling partners to generate the corresponding unsaturated ketones. Contrary to the preceding literature, ketones possessing α-methylene group(s) showed

  在酸性助催化剂的存在下，在合成气气氛下，乙烯基芳族化合物和酮的铂催化串联加氢甲酰化/醛醇缩合反应生成相应的α，β-不饱和酮。在原位事实证明，在各种应用条件下，用各种配体改性后生成的催化剂都是有效的。酸的存在会促进副反应，例如烯烃底物的氢化和醛的副反应分别氢化成相应的烷烃和醇。有趣的是，缩合产物的氢化不是优选的，通过GC-MS只能检测到痕量的饱和产物。通常，在苯乙烯和α-甲基苯乙烯的加氢甲酰化反应中，使用几种酮可以实现中等收率。线性醛被证明在醇醛缩合步骤中更具活性，此外，芳族和环状酮也是可行的偶联伙伴，以生成相应的不饱和酮。与先前的文献相反，
• An efficient and stereoselective Wittig–Horner synthesis of acyclic α-enones with barium hydroxide as solid catalyst
  作者：Carlos Alvarez-Ibarra、Selma Arias、Gabriel Bañón、María J. Fernández、Miguel Rodríguez、Vicente Sinisterra

  DOI：10.1039/c39870001509

  日期：——

  Wittig–Horner reactions under interfacial solid–liquid conditions using activated barium hydroxide catalyst C-200 produce acyclic α-enones with high yields and selectivities.

  使用活化的氢氧化钡催化剂C-200在界面固液条件下进行的Wittig-Horner反应产生了高产率和高选择性的无环α-烯酮。
• Catalytic Enantioselective Synthesis of Vicinal Dialkyl Arrays
  作者：Anthoni W. van Zijl、Wiktor Szymanski、Ferrnando López、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/jo8010649

  日期：2008.9.19

  With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.