4-苯基环己基-1-烯-1-羧酸 | 143287-94-9

• 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: 4-苯基环己基-1-烯-1-羧酸
• 英文名称: 4-phenylcyclohex-1-ene-1-carboxylic acid
• 英文别名: 4-phenylcyclohexene-1-carboxylic acid
• CAS: 143287-94-9
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: YRZUQRSZZQQEBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  4-苯基环己基-1-烯-1-羧酸 在 chromium(VI) oxide 、 dimethyl sulfide borane 、 硫酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 (1s,4s)-4-phenylcyclohexane-1-carboxylic acid
  参考文献：
  名称：

  First Structure−Activity Relationship Study on Dopamine D₃ Receptor Agents with N-[4-(4-Arylpiperazin-1-yl)butyl]arylcarboxamide Structure

  摘要：

  Structure-affinity relationships of N-[4-(4-arylpiperazin-1-yl)butyl]arylcarboxamides as D-3 receptor ligands have been well characterized but not structure-activity relationships. In a first attempt to clarify this issue, seven 1-(2,3dichlorophenyl)piperazine derivatives and their 2-methoxyphenyl counterparts were prepared by varying the arylcarbox-amide moiety. They were tested for D3 receptor binding affinities and in the Eu-GTP binding assay in order to evaluate their intrinsic activity. We have found that the intrinsic activity strongly depended on the nature of the arylearboxamide moiety.

  DOI：

  10.1021/jm050729o
• 作为产物：
  描述：

  4-苯基-环己烷羧酸 在 水 、 permanganate(VII) ion 作用下， 生成 4-苯基环己基-1-烯-1-羧酸
  参考文献：
  名称：

  Rassow, Justus Liebigs Annalen der Chemie, 1894, vol. 282, p. 143

  摘要：

  DOI：

文献信息

• Cobalt-catalyzed carboxylation of aryl and vinyl chlorides with CO₂
  作者：Yanwei Wang、Xiaomei Jiang、Baiquan Wang

  DOI：10.1039/d0cc06451c

  日期：——

  The transition-metal-catalyzed carboxylation of aryl and vinyl chlorides with CO2 is rarely studied, and has been achieved only with a Ni catalyst or combination of palladium and photoredox. In this work, the cobalt-catalyzed carboxylation of aryl and vinyl chlorides and bromides with CO2 has been developed. These transformations proceed under mild conditions and exhibit a broad substrate scope, affording

  很少研究用CO 2过渡金属催化的芳基和氯乙烯的羧化，仅使用Ni催化剂或钯与光氧化还原的混合物即可实现。在这项工作中，已经开发出了用CO 2进行钴催化的芳基，氯乙烯和溴化物的羧化反应。这些转化在温和的条件下进行，并显示出较宽的底物范围，以高至高收率提供了相应的羧酸。
• Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts
  作者：Katsuya Shimomaki、Tomoya Nakajima、Joaquim Caner、Naoyuki Toriumi、Nobuharu Iwasawa

  DOI：10.1021/acs.orglett.9b01340

  日期：2019.6.21

  A visible-light-driven carboxylation of aryl and alkenyl triflates with CO2 is developed by using a combination of Pd and photoredox catalysts. This reaction proceeds under mild conditions and can be applied to a wide range of substrates including acyclic alkenyl triflates.

  通过使用Pd和光氧化还原催化剂的组合，可见光驱动的芳基和烯基三氟甲磺酸酯与CO 2的羧化反应。该反应在温和的条件下进行，可用于多种底物，包括无环烯基三氟甲磺酸酯。
• Cobalt- and Nickel-Catalyzed Carboxylation of Alkenyl and Sterically Hindered Aryl Triflates Utilizing CO₂
  作者：Keisuke Nogi、Tetsuaki Fujihara、Jun Terao、Yasushi Tsuji

  DOI：10.1021/acs.joc.5b02307

  日期：2015.11.20

  cobalt-catalyzed reductive carboxylation reaction of alkenyl trifluoromethanesulfonates (triflates) has been developed. By employing Mn powder as a reducing reagent under 1 atm pressure of CO2 at room temperature, diverse alkenyl triflates can be converted to the corresponding α,β-unsaturated carboxylic acids. Moreover, the carboxylation of sterically hindered aryl triflates proceeds smoothly in the presence of

  已经开发了烯基三氟甲磺酸盐（三氟甲磺酸酯）的高效钴催化的还原羧化反应。通过在室温下在CO 2的1个大气压下使用Mn粉作为还原剂，可以将多种烯基三氟甲磺酸酯转化为相应的α，β-不饱和羧酸。此外，在镍或钴催化剂的存在下，位阻芳基三氟甲磺酸酯的羧化反应平稳进行。
• Activation of Aryl and Vinyl Triflates by Palladium and Electron Transfer – Electrosynthesis of Aromatic and α,β-Unsaturated Carboxylic Acids from Carbon Dioxide
  作者：Anny Jutand、Serge Négri

  DOI：10.1002/(sici)1099-0690(199809)1998:9<1811::aid-ejoc1811>3.0.co;2-v

  日期：1998.9

  The electrochemical reduction of aryl and vinyl triflates in the presence of CO2 and a catalytic amount of palladium results in the formation of aromatic and α,β-unsaturated carboxylic acids. Aryl and vinyl triflates usually undergo palladium-catalysed cross-coupling reactions with nucleophiles. Their reactivity has been reversed in the presence of an electron source, so that they react with electrophiles

  在 CO2 和催化量的钯存在下，芳基和乙烯基三氟甲磺酸酯的电化学还原导致芳族和 α,β-不饱和羧酸的形成。芳基和乙烯基三氟甲磺酸酯通常与亲核试剂发生钯催化的交叉偶联反应。在存在电子源的情况下，它们的反应性会发生逆转，因此它们会与亲电子试剂（如 CO2）发生反应。该反应通过芳基或乙烯基三氟甲磺酸酯的 C-O 键通过氧化加成到钯 (0) 络合物进行活化，然后通过电子转移由此形成的芳基或乙烯基钯 (II) 络合物进行活化。
• Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO₂ Catalyzed by Cuprous Halide
  作者：Junting Hong、Onkar S. Nayal、Fanyang Mo

  DOI：10.1002/ejoc.202000288

  日期：2020.5.22

  Three kinds of alkenyl boron compounds were effectively transformed into the corresponding α, β‐unsaturated carboxylic acids in moderate to high yields through a cuprous halide catalyzed carboxylation with CO2. The advantages of this method include low cost, mild conditions, simple operation, broad scope, and external ligand free.

  通过卤化亚铜与CO 2催化的羧化作用，三种中烯基硼化合物可有效地转化为相应的α，β-不饱和羧酸。该方法的优点包括成本低，条件温和，操作简单，适用范围广以及无需外部配体。