3-环戊基环戊烷-1-酮 | 27610-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-环戊基环戊烷-1-酮
• 英文名称: 3-cyclopentylcyclopentan-1-one
• 英文别名: [1,1'-bi(cyclopentan)]-3-one；3-cyclopentylcyclopentanone；bicyclopentyl-3-one；Bicyclopentyl-3-on；3-Oxo-1-cyclopentyl-cyclopentan；3-Cyclopentylcyclopentanon
• CAS: 27610-86-2
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: KCQKDYIMZAIYIP-UHFFFAOYSA-N

物化性质

• 沸点：
  74-75 °C(Press: 1.3 Torr)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为产物：
  描述：

  3-羟基-1-环戊基环戊烷 在 potassium dichromate 、 硫酸 作用下， 生成 3-环戊基环戊烷-1-酮
  参考文献：
  名称：

  374.将环戊二烯转化为新的双环戊基衍生物；质子磁共振波谱测定结构

  摘要：

  DOI：

  10.1039/jr9610001939

文献信息

• Copper-catalyzed conjugate additions of organozirconocenes. Synthetic and mechanistic studies.
  作者：Peter Wipf、Wenjing Xu、Jacqueline H. Smitrovich、Roman Lehmann、Luigi M. Venanzi

  DOI：10.1016/s0040-4020(01)85058-4

  日期：1994.2

  broad range of functional groups are tolerated in the conjugate addition process. Unsaturated N-acyl oxazolidinones give high diastereoselectivities for the formation of the new asymmetric carbon. The resulting zirconium enolates can be used for tandem aldol addition reactions to aldehydes. Depending on the type of copper salt used, slow or fast formation of copper mirror occurs, but no intermediate

  在3–10 mol％的Cu（l）盐（例如CuBr·S Me 2或CuCN）存在下，烷基锆茂金属很容易添加到α，β-不饱和酮，醛和砜中。反应产率对路易斯酸和碱的存在敏感。在共轭加成过程中可以耐受立体位阻以及广泛的官能团。不饱和氮-酰基恶唑烷酮类对形成新的不对称碳具有高的非对映选择性。所得的烯醇锆可用于醛醇的串联醇醛加成反应。根据所用铜盐的类型，会发生缓慢或快速形成铜镜的现象，但是在光谱学上没有检测到中间的铜物种。因此，提出了一种机理，该机理涉及路易斯酸性的锆茂并烯的烯酮络合，然后烷基取代基的内球转移到螯合的Cu（l）上。
• 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。
• Photomediated synthesis of β-alkylketones from cycloalkanes
  作者：Daniele Dondi、Anna Maria Cardarelli、Maurizio Fagnoni、Angelo Albini

  DOI：10.1016/j.tet.2006.03.028

  日期：2006.6

  beta-Cycloalkyl ketones are prepared through a photomediated radical addition reaction onto enones starting from the corresponding alkanes (i.e., cyclopentane, -hexane, -heptane, -dodecane and adamantane). The alkyl radicals are generated via hydrogen abstraction by either an organic (benzophenone) or an inorganic (tetrabutyl ammonium decatungstate, TBADT) photomediator. Isolated yields vary in the range 30-80%. Benzophenone has to be considered as a reagent, since it is used in an equimolar amount with respect to enone and is completely consumed in the reaction. On the contrary, TBADT is shown to behave as a photocatalyst, which is active for at least 50 cycles. The potential of photomediated reactions for the generation of radicals from unusual precursors and the synthetic significance of this method are discussed. (c) 2006 Elsevier Ltd. All rights reserved.
• Transmetalation reactions of alkylzirconocenes: copper-catalyzed conjugate addition to enones
  作者：Peter Wipf、Jacqueline H. Smitrovich

  DOI：10.1021/jo00023a006

  日期：1991.11

  Rapid hydrozirconation of alkenes by zirconocene hydrochloride, followed by addition of 1 equiv of enone and catalytic amounts of Cu(I) salts, led to the corresponding 1,4-addition products in moderate to high yields and provided the first protocol for in situ preparation of alkyl cuprates from alkenes.
• v. Braun; Kamp; Kopp, Chemische Berichte, 1937, vol. 70, p. 1750,1758
  作者：v. Braun、Kamp、Kopp

  DOI：——

  日期：——