6-phenyl-5-hexenoic acid

• 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: 6-phenyl-5-hexenoic acid
• 英文别名: 6-phenylhex-5-enoic acid
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: GPGLPAFSJGVMEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-phenyl-5-hexenoic acid 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 sodium methylate 、 二异丁基氢化铝 、 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 21.09h， 生成 Methyl 3-oxo-4-(6-phenylhexylsulfanyl)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-溴戊酸 在 dimsyl sodium 作用下， 以 二甲基亚砜 为溶剂， 反应 19.5h， 生成 6-phenyl-5-hexenoic acid
  参考文献：
  名称：

  基于分子间羟醛缩合的新型环断裂

  摘要：

  通过分子内羟醛缩合的环裂解和重构，然后在乙缩醛化条件下（BF 3 /乙二醇）的Grob断裂，被开发成基于分子间羟醛缩合的新型环裂解。在该反应的基础上，将（R，R）-3，5-二甲基环己酮转化为具有间规甲基功能的手性直链化合物。还研究了基于交叉的分子间羟醛缩合的开环反应，并讨论了反应途径。

  DOI：

  10.1016/s0040-4020(01)81545-3

文献信息

• Cyclization of 5-hexenyl radicals from nitroxyl radical additions to 4-pentenylketenes and from the acyloin reaction
  作者：Huda Henry-Riyad、Thomas T Tidwell

  DOI：10.1139/v03-076

  日期：2003.6.1

  Photochemical Wolff rearrangements were used to form 5-substituted-4-pentenylketenes 1a–1d (RCH=CHCH2XCH2CH=C=O: 1a R = H, X = CH2; 1b R = Ph, X = CH2; 1c R = c-Pr, X = CH2; 1d R = H, X = O), which...

  光化学沃尔夫重排用于形成 5-取代-4-戊烯基烯酮 1a??1d (RCH=CHCH2XCH2CH=C=O: 1a R = H, X = CH2; 1b R = Ph, X = CH2; 1c R = c- Pr, X = CH2; 1d R = H, X = O), 其中...
• Synthesis and Evaluation of Novel 2,2-Dimethylthiochromanones as Anti-Leishmanial Agents
  作者：Seán Coll、Mohammad Alhazmi、Patrícia de Aguiar Amaral、Sandra Bourgeade-Delmas、Anne-Cécile Le Lamer、James W. Barlow

  DOI：10.3390/molecules26082209

  日期：——

  based on natural products reported to possess anti-leishmanial action, and their synthetic derivatives. All compounds were elaborated via the key intermediate 2,2,6-trimethoxythiochromanone, which was modified at the benzylic position to afford various ester, amine and amide analogues, substituted by chains of varying lipophilicity. Upon testing in Leishmania, IC50 values revealed the most potent compounds

  在这项工作中，我们描述了一系列基于据报道具有抗利什曼作用的天然产物及其合成衍生物的设计和合成。所有化合物均通过关键中间体2,2,6-三甲氧基硫代苯并二氢吡喃酮进行精制，该中间体在苄基位置进行修饰，得到各种酯，胺和酰胺类似物，并用亲脂性不同的链取代。在利什曼原虫中进行测试后，IC 50值显示出最有效的化合物为苯基烯基和卤代烷基酰胺11a和11e，IC 50值分别为10.5和7.2μM。
• New tandem radical cyclizations directed toward the synthesis of crinipellin A
  作者：C. Eric Schwartz、Dennis P. Curran

  DOI：10.1021/ja00181a033

  日期：1990.12

  tandem radical cyclization strategy for the construction of the congested angular triquinane portion of the naturally occurring tetraquinane crinipellin A. The preparation and cyclization of three 5,5-disubstituted-1,4-dimethyl-1,3-cyclopentadienes are detailed. This cyclization strategy results in a 1,4-functionalization of the cyclopentadiene nucleus, mediated by an allylic radical cyclization. Each

  我们描述了一种新的串联自由基环化策略，用于构建天然四喹烷 crinipellin A 的拥挤角三喹烷部分。 详细介绍了三个 5,5-二取代-1,4-二甲基-1,3-环戊二烯的制备和环化. 这种环化策略导致环戊二烯核的 1,4-官能化，由烯丙基环化介导。每次串联环化以 5:1 的比例产生两种非对映体三喹烷。次要的非对映异构体对 crinipellin A 的 D 环异丙基具有正确的相对立体化学。还描述了与自由基环化平行的串联阳离子环化
• Nitroxyl Radical Reactions with 4-Pentenyl- and Cyclopropylketenes:  New Routes to 5-Hexenyl- and Cyclopropylmethyl Radicals
  作者：Annette D. Allen、Michael F. Fenwick、Huda Henry-Riyad、Thomas T. Tidwell

  DOI：10.1021/jo0102922

  日期：2001.8.1

  in hydrocarbon solvents. The reactions of these ketenes with the nitroxyl radicals tetramethylpiperidinyloxyl (TEMPO, TO*) and tetramethylisoindoline-2-oxyl (TMIO, IO*) form carboxy substituted 5-hexenyl and cyclopropylmethyl radicals which are either trapped by a second nitroxyl radical or undergo rearrangements followed by trapping. The rate constant of the reaction of 4a with TEMPO was similar to

  4-戊烯基酮4a和9以及环丙基烯酮3a，13、14（RCH = C = O）是通过光化学Wolff重排生成的，并且在室温下在烃类溶剂中被IR观察为相对长寿的物种。这些烯酮与硝基氧基四甲基哌啶基氧基（TEMPO，TO *）和四甲基异吲哚啉-2-氧基（TMIO，IO *）的反应形成羧基取代的5-己烯基和环丙基甲基，它们被第二个硝基氧基所俘获或进行重排通过诱捕。4a与TEMPO的反应速率常数与n-BuCH = C = O（1b）相似，而3a的反应速率高4.3倍，表明初始自由基的环丙基稳定性。
• Development of an Enzyme-Linked Immunosorbent Assay for the Determination of the Linear Alkylbenzene Sulfonates and Long-Chain Sulfophenyl Carboxylates Using Antibodies Generated by Pseudoheterologous Immunization
  作者：Javier Ramón-Azcón、Roger Galve、Francisco Sánchez-Baeza、M.-Pilar Marco

  DOI：10.1021/ac051141s

  日期：2006.1.1

  ELISA methods have been developed for screening contamination of water resources by linear alkyl benzene sulfonates (LAS) or the most immediate degradation products, the long chain sulfophenyl carboxylates, SPCs. The assay uses antibodies raised through pseudoheterologous immunization strategies using an equimolar mixture of two immunogens (SFA−KLH and 13C13-SPC−KLH) prepared by coupling N-(4-alkylphenyl)sulfonyl-3-aminopropanoic acid (SFA) and p-(1-carboxy-13-tridecyl)phenylsulfonic acid (13C13-SPC) to keyhole limpet hemocyanin (KLH). The immunizing haptens have been designed to address recognition versus two different epitopes of the molecule. The SFA hapten maximizes recognition of the alkyl moiety while preserving the complexity of the different alkyl chains present in the LAS technical mixture. The 13C13-SPC hapten addresses recognition of the common and highly antigenic phenylsulfonic group. The antisera raised using this strategy have been shown to be superior to those obtained through homologous immunization procedures using a single substance. By using an indirect ELISA format, LAS and long-chain SPCs can be detected down to 1.8 and 0.2 μg L-1, respectively. Coefficients of variation of 6 and 12% within and between assays, respectively, demonstrate immunoassay reproducibility. The assay can be used in media with a wide range of pH and ionic strength values. Preliminary experiments performed to assess matrix effects have demonstrated the potential applicability of the method as a screening tool to assess contamination by these types of surfactants in natural water samples.

  已经开发出 ELISA 方法来筛查直链烷基苯磺酸盐 (LAS) 或最直接的降解产物长链磺基苯磺酸盐 (SPC) 对水资源的污染。该测定使用通过伪异源免疫策略产生的抗体，使用通过偶联 N-(4-烷基苯基)磺酰基-3-氨基丙酸 (SFA) 和 p-( 1-羧基-13-十三烷基)苯磺酸 (13C13-SPC) 生成匙孔血蓝蛋白 (KLH)。免疫半抗原被设计用于识别分子的两个不同表位。 SFA 半抗原最大限度地识别烷基部分，同时保留 LAS 技术混合物中存在的不同烷基链的复杂性。 13C13-SPC 半抗原可识别常见且高抗原性的苯磺酸基团。使用这种策略产生的抗血清已被证明优于使用单一物质通过同源免疫程序获得的抗血清。通过使用间接 ELISA 格式，可以分别检测低至 1.8 和 0.2 μg L-1 的 LAS 和长链 SPC。测定内和测定间的变异系数分别为 6% 和 12%，证明了免疫测定的重现性。该测定可用于具有广泛 pH 值和离子强度值的介质。为评估基质效应而进行的初步实验已证明该方法作为筛选工具的潜在适用性，以评估天然水样中这些类型的表面活性剂的污染。