5-phenylpenta-2,4-dienoic acid | 185152-35-6

• 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-phenylpenta-2,4-dienoic acid
• 英文别名: (4E)-5-phenylpenta-2,4-dienoic acid；cinnamylidenacetic acid；β-Styrylacrylsaeure
• CAS: 185152-35-6
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: FEIQOMCWGDNMHM-HQMTTWOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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-phenylpenta-2,4-dienoic acid 在 氢氟酸 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 以63%的产率得到(4E)-5-phenylpenta-2,4-dienoyl fluoride and (4Z)-5-phenylpenta-2,4-dienoyl fluoride
  参考文献：
  名称：

  N-叔丁基三唑基亚烷基：α，β-不饱和酰基偶氮对映选择性（3 + 2）环化的催化剂

  摘要：

  但（基）不徒劳：的范围ñ -叔已经制备丁基取代triazolylidene N-杂环卡宾。其中，吗啉酮衍生的催化剂（1）被证明最适合从供体-受体环丙烷和α，β-不饱和酰基氟对映体选择性合成环戊烷。通过13 C NMR分析，该催化剂的性能与催化剂的电子性质相关。MS ＝分子筛，TMS ＝三甲基甲硅烷基。

  DOI：

  10.1002/anie.201304081
• 作为产物：
  描述：

  (2E,4E)-5-Phenyl-penta-2,4-dienoic acid methyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 水 、 二乙二醇 为溶剂， 反应 0.25h， 以100%的产率得到5-phenylpenta-2,4-dienoic acid
  参考文献：
  名称：

  Polymer-Assisted Solution-Phase Synthesis Under Combined Ultrasound and Microwave Irradiation: Preparation of α,β-Unsaturated Esters and Carboxylic Acids, Key Intermediates of Novel Sigma Ligands

  摘要：

  The optimal conditions to prepare ,-unsaturated methyl esters via Wittig reaction combining polymer-assisted solution-phase synthesis (PASPS) methodology and simultaneous ultrasound and microwave irradiation were established. The effects of temperature, solvent, and irradiation time were discussed. Results clearly indicated the superiority of combined ultrasound and microwave-assisted procedure over microwave-assisted methodology. Moreover, an efficient PASPS procedure to prepare ,-unsaturated carboxylic acids via tandem Wittig olefination and hydrolysis reaction was developed under combined ultrasound and microwave irradiation. Generally, a good conversion of aldehydes to acids was observed. The optimized protocols allowed us to quickly prepare a small collection of either ,-unsaturated esters or carboxylic acids, key intermediates for the drug-discovery process of new sigma ligands.

  DOI：

  10.1080/00397910902738112

文献信息

• Ni-Catalyzed Site-Selective Dicarboxylation of 1,3-Dienes with CO₂
  作者：Andreu Tortajada、Ryo Ninokata、Ruben Martin

  DOI：10.1021/jacs.7b13220

  日期：2018.2.14

  A site-selective catalytic incorporation of multiple CO2 molecules into 1,3-dienes en route to adipic acids is described. This protocol is characterized by its mild conditions, excellent chemo- and regioselectivity and ease of execution under CO2 (1 atm), including the use of bulk butadiene and/or isoprene feedstocks.

  描述了一种位点选择性催化将多个 CO2 分子结合到 1,3-二烯到己二酸的过程中。该协议的特点是条件温和，具有出色的化学和区域选择性，并且在 (1 atm) 下易于执行，包括使用散装丁二烯和/或异戊二烯原料。
• Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids
  作者：Xiao-Yu Lu、Jin-Song Li、Shi-Qun Wang、Yu-Jing Zhu、Yue-Ming Li、Lu-Yu Yan、Jia-Mei Li、Jin-Yu Wang、Hai-Pin Zhou、Xiu-Tao Ge

  DOI：10.1039/c9cc04795f

  日期：——

  A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as

  已开发出Pd催化的α，β-不饱和羧酸与环状和非环状环氧化物的脱羧交叉偶联。β-单取代的和β-二取代的不饱和羧酸以及共轭二烯不饱和羧酸都是合适的反应底物。以中等至良好的产率获得了取代的均烯丙基醇。获得的产物为有利于环状环氧化物的抗非对映异构体的非对映异构体的混合物。这项工作提供了一种改性复杂的包含α，β-不饱和羧酸的有机分子的方法。
• Electrochemical Intermolecular Monofluoroalkylation of α,β-Unsaturated Carboxylic Acids and Heteroaromatics with 2-Fluoromalonate Esters
  作者：Zhong-Wei Hou、Ting Jiang、Ting-Xia Wu、Lei Wang

  DOI：10.1021/acs.orglett.1c03284

  日期：2021.11.5

  An electrochemical approach for the preparation of monofluorides from α,β-unsaturated carboxylic acids and heteroaromatics with readily available 2-fluoromalonate esters as monofluoroalkyl radical precursors has been developed. The electrosynthesis employs ferrocene (Cp2Fe) as a catalyst in a simple undivided cell with a broad substrate scope, which obviates the need for sacrificial oxidizing reagents

  已经开发了一种用于从 α,β-不饱和羧酸和杂芳烃制备单氟化物的电化学方法，使用容易获得的 2-氟丙二酸酯作为单氟烷基自由基前体。电合成采用二茂铁 (Cp 2 Fe) 作为催化剂，在一个简单的未分割电池中，底物范围广泛，无需牺牲氧化剂。
• Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis
  作者：Pan Xu、Ablimit Abdukader、Kaidong Hu、Yixiang Cheng、Chengjian Zhu

  DOI：10.1039/c3cc48598f

  日期：——

  A visible-light-induced decarboxylative trifluoromethylation of alpha,beta-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed. The corresponding trifluoromethylated alkenes were obtained in moderate to high yields with excellent functional group tolerance at ambient temperature. Preliminary mechanistic analyses suggest a radical-type mechanism.

  公开了使用Togni试剂作为CF 3源的可见光诱导的α，β-不饱和羧酸的脱羧三氟甲基化。以中等至高产率获得了相应的三氟甲基化烯烃，其在环境温度下具有优异的官能团耐受性。初步的机械分析表明是一种激进型机制。
• Knoevenagel-Doebner condensation promoted by chitosan as a reusable solid base catalyst
  作者：Nagaraj Anbu、Surendran Hariharan、Amarajothi Dhakshinamoorthy

  DOI：10.1016/j.mcat.2019.110744

  日期：2020.3

  although Knoevenagel-Doebner condensation reaction has been reported with many organocatalysts including proline, no attempts were made to develop heterogeneous catalysts with environmental concerns. Considering these factors in mind, the title reaction is studied with chitosan as a heterogeneous solid base catalyst for the synthesis of α,β-unsaturated carboxylic acids through the condensation followed

  使用天然存在的生物聚合物开发绿色和可持续性工艺正成为替代传统催化系统的合适方法之一，传统催化系统会产生大量具有高风险因素的副产物。在这种情况下，尽管已经报道了Knoevenagel-Doebner与包括脯氨酸在内的许多有机催化剂的缩合反应，但未尝试开发涉及环境问题的多相催化剂。考虑到这些因素，以壳聚糖为多相固体碱催化剂研究了标题反应，该反应通过缩合然后脱羧反应合成α，β-不饱和羧酸。壳聚糖具有许多优势，例如浸出，可重复使用性测试，广泛的底物范围，并以更高的纯度提供所需产品的更高产量。粉末X射线衍射（XRD），傅立叶变换红外光谱（FT-IR），扫描电子显微镜（SEM）和元素分析表明，在优化反应条件下，催化前后壳聚糖的结构完整性和形态没有重大变化。情况。