5-phenyl-4-penten-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-phenyl-4-penten-1-ol
• 英文别名: 5-phenyl-pent-4-en-1-ol；5-Phenyl-4-pentenol；5-phenylpent-4-en-1-ol
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: QBQBSEZWJAWWCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  5-phenyl-4-penten-1-ol 在 platinum(IV) oxide potassium dihydrogenphosphate 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 38.59h， 生成 Methyl 3-cyano-3-hydroxy-4-(5-phenylpentylsulfanyl)butanoate
  参考文献：
  名称：

  ATP-Citrate Lyase as a Target for Hypolipidemic Intervention. Design and Synthesis of 2-Substituted Butanedioic Acids as Novel, Potent Inhibitors of the Enzyme

  摘要：

  ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of a-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme, The best compounds, 58, 68, 71, 74 have reversible K-i's in the 1-3 mu M range against the isolated rat enzyme, As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP-citrate lyase.

  DOI：

  10.1021/jm960167w
• 作为产物：
  描述：

  5-苯基-4-戊炔-1-醇 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到5-phenyl-4-penten-1-ol
  参考文献：
  名称：

  Pd（II）催化的[4 + 2]杂环序列用于多杂环生成

  摘要：

  报道了一种新的Pd（II）催化的级联序列，用于从简单的起始原料形成多杂环。该序列适用于吲哚和吡咯底物，并且可以接受一定范围的取代基。该反应被认为是通过Pd（II）催化的C–H活化的Heck反应进行的，然后是第二个Pd（II）催化的aza-Wacker反应，每个序列有两个Cu（II）介导的Pd（0）转换。该序列可以被认为是正式的[4 + 2]杂环化。

  DOI：

  10.1021/acs.orglett.8b02543
• 作为试剂：
  描述：

  在 5-phenyl-4-penten-1-ol 作用下， 以 乙酸乙酯 为溶剂， 以77 %的产率得到
  参考文献：
  名称：

  CN116655602

  摘要：

  公开号：

文献信息

• Intramolecular Anodic Olefin Coupling Reactions and the Synthesis of Cyclic Amines
  作者：Hai-Chao Xu、Kevin D. Moeller

  DOI：10.1021/ja910586v

  日期：2010.3.3

  Anodic olefin coupling reactions using a tosylamine trapping group have been studied. The cyclizations are favored by the use of a less-polar radical cation and more basic reaction conditions. The most significant factor for obtaining good yields of cyclic product is the use of the more basic reaction conditions. However, a number of factors including the nature of both the solvent and the electrolyte

  已经研究了使用甲苯磺胺捕获基团的阳极烯烃偶联反应。使用极性较小的自由基阳离子和碱性更强的反应条件有利于环化。获得良好的环状产物收率的最重要因素是使用更碱性的反应条件。然而，包括所用溶剂和电解质的性质在内的许多因素会影响环化的产率。环化允许快速合成取代的脯氨酸和哌啶酸类型的衍生物。
• Palladium-Catalyzed Aerobic Oxidative Cyclization of Aliphatic Alkenyl Amides for the Construction of Pyrrolizidine and Indolizidine Derivatives
  作者：Dan Yang、Kai-Yip Lo、Liu Ye

  DOI：10.1055/s-0036-1588502

  日期：2017.8

  An efficient palladium-catalyzed aerobic oxidative cyclization has been developed to synthesize a variety of pyrrolizidine and indolizidine derivatives from simple aliphatic alkenyl amides in moderate to good yields. The reaction features the capability of accessing various N-heterocycles and the use of molecular oxygen (1 atm) as the green oxidant.

  已经开发出一种有效的钯催化的有氧氧化环化反应，以中等至良好的产率从简单的脂肪族烯基酰胺合成各种吡咯里西啶和吲哚里西啶衍生物。该反应具有访问各种 N-杂环的能力和使用分子氧 (1 atm) 作为绿色氧化剂的能力。
• Alkoxyl Radicals Generated under Photoredox Catalysis: A Strategy for anti‐Markovnikov Alkoxylation Reactions
  作者：Anne‐Laure Barthelemy、Béatrice Tuccio、Emmanuel Magnier、Guillaume Dagousset

  DOI：10.1002/anie.201806522

  日期：2018.10.15

  involves alkoxyl radicals generated from N‐alkoxypyridinium salts. A wide range of alkenes are smoothly difunctionalized in an anti‐Markovnikov fashion, affording various functionalized alkyl alkyl ethers. Notably, this mild process tolerates a number of functional groups and is efficiently carried out under both batch and flow conditions. Importantly, electron paramagnetic resonance (EPR) experiments

  本文报道的是一种新型的光氧化还原催化的醚合成方法，它涉及由N-烷氧基吡啶鎓盐生成的烷氧基自由基。各种各样的烯烃以反马尔可夫尼可夫的方式平稳地进行双官能化，从而提供了各种官能化的烷基烷基醚。值得注意的是，这种温和的方法可以耐受许多官能团，并且可以在间歇和流动条件下有效地进行。重要的是，通过自旋俘获进行了电子顺磁共振（EPR）实验，以表征参与该自由基/阳离子过程的自由基中间体。
• Intramolecular cyclization of acetylenic homoallylic ketones mediated by the addition of stannyl radicals; a short facile pathway to α-methylene-β-substituted cyclopentanones
  作者：Eun Lee、Chang-Uk Hur、Jeong-Ho Park

  DOI：10.1016/s0040-4039(01)93939-5

  日期：1989.1

  α-(Stannyl)methylenecyclopentanones are obtained by tributylstannane addition reactions of acetylenic homoallylic ketones. α-Methylenecyclopentanones are produced upon destannylation.

  通过炔属均烯丙基酮的三丁基锡烷加成反应获得α-（苯乙烯基）亚甲基环戊酮。α-亚甲基环戊酮在脱锡时产生。
• Metal-Free Oxyaminations of Alkenes Using Hydroxamic Acids
  作者：Valerie A. Schmidt、Erik J. Alexanian

  DOI：10.1021/ja204255e

  日期：2011.8.3

  A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations

  描述了一种自由基介导的无金属烯烃氧胺化方法。该方法利用烯烃加成中脒氧基自由基的独特反应性，使用简单的偶氮二甲酸二异丙酯 (DIAD) 作为自由基陷阱提供一般的双官能化。该协议利用该过程的分子内性质，在所有情况下提供单一区域异构体。环状烯烃的双官能化提供了使用当前方法无法获得的具有高立体选择性的反式氧胺化产物，补充了顺式选择性氧胺化过程。