5-phenyl-4-pentenoic 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: 5-phenyl-4-pentenoic acid
• 英文别名: Cinnamylessigsaeure；3-Styrylpropionic acid；5-phenylpent-4-enoic acid
• 化学式: C₁₁H₁₂O₂
• mdl: MFCD01926594
• 分子量: 176.215
• InChiKey: ISCHCBAXHSLKOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 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：

  5-phenyl-4-pentenoic acid 在 platinum(IV) oxide potassium dihydrogenphosphate 、 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 39.09h， 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-phenylpent-2-enoic acid 在 sodium hydroxide 作用下， 生成 5-phenyl-4-pentenoic acid
  参考文献：
  名称：

  Bougault, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911, vol. 152, p. 197

  摘要：

  DOI：

文献信息

• Hexafluoroisopropanol‐Promoted Haloamidation and Halolactonization of Unactivated Alkenes
  作者：Chenxiao Qi、Guillaume Force、Vincent Gandon、David Lebœuf

  DOI：10.1002/anie.202010846

  日期：2021.1.11

  intermediate is typically mentioned, but limited mechanistic evidence supports it. Reported here is an efficient metal‐ and oxidant‐free protocol to achieve the haloamidation of olefins, promoted by hexafluoroisopropanol, along with a DFT investigation of the mechanism. These findings should guide the future development of more complex transformations in the field of halofunctionalization.

  带有卤化物官能团的吡咯烷和哌啶衍生物是药物发现中的主要组成部分，因为卤化物可以充当后修饰的锚点。原则上，构建这些框架的最简单方法之一是烯烃的卤化。尽管在该领域已经取得了进展，特别是随着对映选择性形式的发展，但是该反应在反应性方面仍然充满局限性。此外，剩下的主要问题是了解工作机制。通常提到卤化中间产物的形成，但是有限的机械证据支持它。此处报道的是一种有效的无金属和氧化剂的方案，可实现由六氟异丙醇促进的烯烃的卤代酰胺化反应，以及对该机理的DFT研究。
• Gallium-catalyzed reductive lactonization of γ-keto acids with a hydrosilane
  作者：Norio Sakai、Shuhei Horikawa、Yohei Ogiwara

  DOI：10.1039/c6ra19286f

  日期：——

  Described herein is the GaCl3-catalyzed lactonization of γ-keto carboxylic acids in the presence of PhSiH3 leading to the direct preparation of γ-lactone derivatives. This reducing system showed a relatively wide functional group tolerance.

  本文描述了在PhSiH 3存在下GaCl 3催化的γ-酮羧酸的内酯化，从而直接制备γ-内酯衍生物。该还原体系显示出相对宽泛的官能团耐受性。
• Stereoselective synthesis of 4- or 5-substituted 2-benzyl- and 2-benzoylpyrrolidines by means of anodic oxidation of δ-alkenylamines
  作者：Masao Tokuda、Tohru Miyamoto、Hirotake Fujita、Hiroshi Suginome

  DOI：10.1016/s0040-4020(01)87064-2

  日期：——

  The anodic oxidation of the lithium amides of δ-alkenylamines 6a, 6b, 6c, 10a, and 10b gave stereoselectively cis-5-substituted 2-benzyl-1-methylpyrrolidines (7a,7b,7c) and 4-substituted 2-benzyl-1-methyl-pyrrolidines (11a, 11b) in high yields. The anodic oxidation of N-methoxyl compounds of δ-alkenylamines (12a, 12b) gave 5-substituted 2-benzoyl-1-methylpyrrolidines (13a, 13b).

  δ-alkenylamines的锂酰胺的阳极氧化6a，图6b，图6c，图10a，和图10b给出立体选择性顺-5-取代的2-苄基-1- methylpyrrolidines（7A，7B，7C）和4-取代的2-苄基1-甲基吡咯烷（11a，11b）高产率。δ-烯基胺的N-甲氧基化合物的阳极氧化（12a，12b）得到5-取代的2-苯甲酰基-1-甲基吡咯烷（13a，13b）。
• C(alkenyl)–H Activation via Six-Membered Palladacycles: Catalytic 1,3-Diene Synthesis
  作者：Mingyu Liu、Pusu Yang、Malkanthi K. Karunananda、Yanyan Wang、Peng Liu、Keary M. Engle

  DOI：10.1021/jacs.8b02124

  日期：2018.5.2

  prepare highly substituted 1,3-dienes from two different alkenes is described using a directed, palladium(II)-mediated C(alkenyl)-H activation strategy. The transformation exhibits broad scope across three synthetically useful substrate classes masked with suitable bidentate auxiliaries (4-pentenoic acids, allylic alcohols, and bishomoallylic amines) and tolerates internal nonconjugated alkenes, which

  描述了一种使用定向的、钯 (II) 介导的 C(烯基)-H 活化策略从两种不同的烯烃制备高度取代的 1,3-二烯的催化方法。该转化在三种合成有用的底物类别中表现出广泛的范围，这些底物被合适的双齿助剂（4-戊烯酸、烯丙醇和双烯丙基胺）掩盖，并且可以耐受内部非共轭烯烃，这些烯烃在此类化学中历来是具有挑战性的一类底物。催化转化是通过 MnO2 作为化学计量氧化剂或共催化 Co(OAc)2 和 O2 (1 atm) 实现的。进行了实验和计算研究以阐明对 C(烯基)-H 激活的偏好超过其他潜在途径。作为这项努力的一部分，
• Enantioselective bromolactonization of cis-1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst
  作者：Chong Kiat Tan、Chencheng Le、Ying-Yeung Yeung

  DOI：10.1039/c2cc31148h

  日期：——

  A facile, highly regio- and enantioselective amino-thiocarbamate-catalyzed bromolactonization of cis-1,2-disubstituted olefinic acids has been developed. The use of the enantio-enriched lactones in the synthesis of chiral synthetic intermediates is also demonstrated.

  已经开发了一种容易的，高度区域和对映选择性的氨基-硫代氨基甲酸酯催化的顺式1,2-二取代的烯烃酸的溴内酯化反应。还证明了对映体富集的内酯在手性合成中间体的合成中的用途。