3-环戊基环己酮 | 27608-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-环戊基环己酮
• 英文名称: 3-cyclopentylcyclohexanone
• 英文别名: 3-Cyclopentylcyclohexan-1-one
• CAS: 27608-11-3
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: AXLUILPBCDDHGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  255.4±8.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium dichromate 、 硫酸 、 水 作用下， 生成 3-环戊基环己酮
  参考文献：
  名称：

  Mousseron; Mousseron-Canet, Bulletin de la Societe Chimique de France, 1956, p. 1220,1224

  摘要：

  DOI：

文献信息

• Reductive free-radical alkylations and cyclisations mediated by 1-alkylcyclohexa-2,5-diene-1-carboxylic acids
  作者：Paul A. Baguley、John C. Walton

  DOI：10.1039/a802024h

  日期：——

  1-alkylcyclohexa-2,5-diene-1-carboxylic acids were prepared by Birch reduction–alkylation of benzoic acid and their efficiency as mediators of alkyl radical chain addition and cyclisation processes was investigated. Reductive alkylations were respectably successful, even with only one or two equivalents of alkene, for secondary, tertiary and benzylic radicals. Reaction of 1-[2-(cyclohex-2-enyloxy)ethyl]cyclohexa-2

  通过对苯甲酸进行Birch还原-烷基化反应，制备了一系列1-烷基环六-2,5-二烯-1-羧酸，并研究了它们作为烷基链加成和环化过程的介质的效率。对于仲，叔和苄基，即使仅使用一或两个当量的烯烃，还原烷基化也相当成功。1-反应[2-（环己-2-烯基氧基）乙基]环己-2,5-二烯-1-羧酸，得到的产品外切- TRIG -cyclisation，即7-氧杂二环[4.3.0]壬烷，在产率与氢化三丁基锡诱导的3-（2'-碘乙氧基）环己烯的环化反应相当。这以及exo-和end的隔离1- [2-（6,6-二甲基双环[3.1.1]庚-2-烯-2-基甲氧基）乙基]环六-2,5-二烯-1-羧酸的环化产物确定闭环也可以用这些试剂令人满意地介导。制剂完全不含金属污染物，并且在添加或环化之前完全不存在烷基的直接还原。然而，所需的产物伴随有烷基苯，以及引发剂分解的副产物，并且这种复杂的后处理。在反式的桦木还原烷基化中未能获得1-
• Direct β-Alkylation of Ketones and Aldehydes via Pd-Catalyzed Redox Cascade
  作者：Chengpeng Wang、Guangbin Dong

  DOI：10.1021/jacs.8b03530

  日期：2018.5.16

  report a direct β-alkylation of ketones and aldehydes with simple alkyl bromides through a Pd-catalyzed redox-cascade strategy. The use of a Cu cocatalyst is important for improved efficiency. The reaction is redox-neutral, without the need for strong acids or bases. Both cyclic and acyclic ketones, as well as α-branched aldehydes, are suitable substrates for coupling with secondary and tertiary alkyl

  我们报告了通过 Pd 催化的氧化还原级联策略用简单的烷基溴对酮和醛进行直接 β-烷基化。铜助催化剂的使用对于提高效率很重要。该反应是氧化还原中性的，不需要强酸或强碱。环状和无环酮以及α-支化醛都是与仲和叔烷基溴偶联的合适底物。Zanapezil 的简明正式合成是使用这种 β-烷基化方法实现的。
• Preparation of 1-phenylcyclohexa-2,5-diene-1-carboxylates and their use in free-radical mediated synthesesElectronic supplementary information (ESI) available: experimental procedures for the preparation of 1,4-dihydrobiphenyl,9 1-deuterio-1,4-dihydrobiphenyl, 1-phenylcyclohexa-2,5-diene-1-carboxylic acid with 3,4-dihydrobiphenyl-3-carboxylic acid, 2-(cyclohex-2-enyloxy)ethyl 1-phenylcyclohexa-2,5-diene-1-carboxylate and non-1-en-6-ol. Experimental details of the reactions of cyclopentyl 1-phenylcyclohexa-2,5-diene-1-carboxylate with cyclohexenone, methyl acrylate, methyl methacrylate, acrylonitrile and cyclohexene are included. See http://www.rsc.org/suppdata/p1/b1/b110527m/
  作者：Paul A. Baguley、Leon V. Jackson、John C. Walton

  DOI：10.1039/b110527m

  日期：2002.1.23

  Synthetic routes to pure 1-phenylcyclohexa-2,5-diene-1-carboxylic acid and derived esters were developed. Esters containing appropriately unsaturated side chains generated the corresponding alkenyl radicals and hence gave good yields of 5-exo ring closure products in organotin-free reactions. Extrusion of phenyl radicals from the intermediate cyclohexadienyl type radicals was not observed, and this alternative β-scission did not compete under any conditions. Yields from alkylations of olefins in analogous intermolecular processes were, however, poor. As a spin-off from the research, it was found that 1-phenylcyclohexa-2,5-diene-1-carboxylic acid (6) was a useful source of hydroxyformyl (formate) radicals in organic solvents.

  开发了纯 1-苯基环己-2,5-二烯-1-羧酸及其衍生酯的合成路线。含有适当不饱和侧链的酯类可生成相应的烯基自由基，因此在无有机锡反应中，5-外环闭合产物的产量很高。没有观察到苯基自由基从中间的环己二烯型自由基中挤出，而且这种替代性的 β 分裂在任何条件下都不会产生竞争。不过，在类似的分子间过程中，烯烃烷基化的产量很低。研究的一个附带成果是发现 1-苯基环己-2,5-二烯-1-羧酸（6）是有机溶剂中羟基甲酰（甲酸）自由基的有效来源。
• Regioselective radical ring-opening reaction of bicyclo[4.2.0]octan-2-ones promoted by samarium(II) iodide
  作者：Kiyomi Kakiuchi、Koichi Minato、Ken Tsutsumi、Tsumoru Morimoto、Hideo Kurosawa

  DOI：10.1016/s0040-4039(03)00085-6

  日期：2003.2

  Radical ring-opening reactions of bicyclo[4.2.0]octanones, its C6 alkyl derivatives, and tricyclic ketones promoted by SmI2 gave cyclohexanones via fission of the external cyclobutane bond. The CO2Me, CN, and phenyl derivatives led to the production of the eight-membered ring compounds through cleavage of the central cyclobutane bond. Using this regioselective reaction, the synthesis of (±)-acorenone

  双环[4.2.0]辛酮，其C6烷基衍生物和SmI 2促进的三环酮的自由基开环反应通过外部环丁烷键的裂变产生环己酮。CO 2 Me，CN和苯基衍生物通过裂解中央环丁烷键而导致生成八元环化合物。使用该区域选择性反应，实现了（±）-aco烯酮的合成。
• The photochemical cycloaddition reaction of 2-cyclohexenone with alkenes: Trapping of triplet 1,4-biradical intermediates with hydrogen selenide
  作者：David J. Maradyn、Alan C. Weedon

  DOI：10.1016/0040-4039(94)88255-x

  日期：1994.10

  the alkene that becomes bonded to the enone in the biradical intermediates. The yields of the trapped biradicals indicate that the regiochemistry of the photocycloaddition reaction is determined by the manner in which the biradicals partition between fragmentation to give ground state starting materials and closure to give product, and not by their relative rates of formation. The results suggest that

  在2-环己烯酮与烯烃环戊烯和乙氧基乙烯之间的光化学环加成反应中形成的三重1，4-双自由基中间体已被硒化氢定量捕集。双自由基的结构表明，它们是通过烯酮的2位和3位都键合到烯烃的一个末端上而形成的。在乙氧基乙烯的情况下，在双自由基中间体中，只有烯键取代度较低的末端才与烯酮键合。被捕获的双基自由基的产率表明，光环加成反应的区域化学是由双基自由基在断裂以给出基态起始材料和闭合以得到产物之间分配的方式决定的，而不是由它们的相对形成速率决定的。