3-phenyl-5-propyl-2-cyclohexenone | 137204-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-phenyl-5-propyl-2-cyclohexenone
• 英文别名: 3-Phenyl-5-propylcyclohex-2-en-1-one
• CAS: 137204-62-7
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: PSJRFFNKFAGYNA-UHFFFAOYSA-N

物化性质

• 沸点：
  322.0±32.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-三甲基硅烷-1-己炔 在 sodium hydroxide 、 正丁基锂 、 双三氟甲烷磺酰亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 3-phenyl-5-propyl-2-cyclohexenone
  参考文献：
  名称：

  Brønsted Acid-Promoted Cyclizations of Siloxyalkynes with Arenes and Alkenes

  摘要：

  We have described the first Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes to afford substituted tetralone and cyclohexenone derivatives. The most notable aspect of the carbocyclizations involving siloxyalkynes is the ability to employ a range of substrates that are not restricted to those containing electron-rich arenes and alkenes. The key mechanistic feature of the reaction is the generation of a highly reactive ketenium ion upon protonation of siloxyalkyne. We believe that the low nucleophilicty of the counteranion is crucial for enabling the formation and effective interception of this highly reactive intermediate.

  DOI：

  10.1021/ja046586x

文献信息

• Aldol Reaction and Robinson-Type Annelation Catalyzed by Lanthanoid Triisopropoxides
  作者：Tamon Okano、Yoshikazu Satou、Motoshi Tamura、Jitsuo Kiji

  DOI：10.1246/bcsj.70.1879

  日期：1997.8

  Lanthanoid triisopropoxides are active catalysts for aldol reactions. Aldehydes give the corresponding β-hydroxyaldehydes at low temperatures in good yields, whereas ketones are less reactive, but form condensation products at high temperatures. Exceptionally, γ- or δ-diketones easily undergo condensation to give five- and six-membered unsaturated ketones in high yields. The lanthanoid propoxides, catalyzing the Michael addition of ketones to α,β-unsaturated ketones, which give δ-diketones, are also good catalysts for the Robinson-type annelation. In these reactions, the catalytic activity of the lanthanum propoxide is higher than those of the heavy lanthanoid propoxides, and is almost comparable to that of sodium isopropoxide. Since aluminum triisopropoxide shows poor activity, the lanthanoid propoxides are considerably basic for trivalent metal alkoxides.

  镧系三异丙醇盐是醛醇反应的活性催化剂。在低温下，醛能够高效地生成相应的β-羟基醛，而酮的反应活性较低，但在高温下会形成缩合产物。特别地，γ-或δ-二酮很容易发生缩合反应，以高产率生成五元和六元的非饱和酮。镧系异丙醇盐还具有催化酮对α,β-非饱和酮的迈克尔加成反应，这种反应会生成δ-二酮，同时也是罗宾逊型环加成反应的良好催化剂。在这些反应中，镧异丙醇盐的催化活性高于重镧系异丙醇盐，几乎可与钠异丙醇盐相媲美。由于铝三异丙醇盐的活性较差，镧系异丙醇盐相对于三价金属醇盐具有相当强的碱性。
• Brønsted acid-promoted cyclizations of siloxy alkynes with unactivated arenes, alkenes, and alkynes
  作者：Liming Zhang、Jianwei Sun、Sergey A. Kozmin

  DOI：10.1016/j.tet.2006.06.037

  日期：2006.12

  found that trifluoromethane sulfonimide (HNTf2) proved to be a superior promoter of these reactions compared to a range of other Brønsted acids. This finding could be attributed to a high acidity of HNTf2 in aprotic organic solvents combined with a low nucleophilicity of the NTf2− anion. Depending on the nature of the nucleophile, the carbocyclizations proceeded either via 6-endo-dig or 5-endo-dig manifolds

  在本文中，我们描述了开发新的碳-碳键形成过程的一般概念，该概念基于布朗斯台德酸介导的甲硅烷氧基炔烃的活化作用，然后有效截获所得的高反应性离子通过未活化的芳烃，烯烃或炔烃。我们发现，与一系列其他布朗斯台德酸相比，三氟甲烷磺酰亚胺（HNTf 2）被证明是这些反应的优良促进剂。这一发现可以归因于HNTf的高酸度2与所述NTF的低亲核性组合非质子有机溶剂2 -阴离子。根据亲核试剂的性质，碳环化可通过6-endo-dig或5个内挖式歧管。在1-甲硅烷基-1,5-二炔的情况下，环化反应伴随着卤化物的抽象或芳基化。
• Dienediolates of unsaturated carboxylic acids in synthesis. Synthesis of cyclohexenones and polycyclic ketones by tandem Michael-Dieckmann decarboxylative annulation of unsaturated carboxylic acids.
  作者：María J. Aurell、Pablo Gaviña、Ramon Mestres

  DOI：10.1016/s0040-4020(01)86973-8

  日期：1994.2

  Substituted 2-cyclohexenones 4 to 7 and hexaxydronaphthalenones and hexahydroindenones 13 to 18 are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of acyclic and alicyclic unsaturated carboxylic acids to the lithium salts of the same or other unsaturated carboxylic acids.

  通过将无环和脂环式不饱和羧酸的二烯二醇锂串联加入相同或其他不饱和羧酸的锂盐中来制备取代的2-环己烯酮4至7和六氢萘二烯酮和六氢茚并酮13至18。
• Dienediolates of Unsaturated Carboxylic Acids in Synthesis. Tandem Michael Diechmann Synthesis of Substituted 2-Cyclohexenones
  作者：M. J. Aurell、P. Gaviña、S. Gil、A. Tortajada、R. Mestres

  DOI：10.1080/00397919108021772

  日期：1991.9

  3,5-Disubstituted 2-Cyclohexenones are prepared by tandem Michael-Dieckmann addition of lithium dienediolates of dimethylacrylic and beta-methylcinnamic acids to lithium carboxylates of unsaturated carboxylic acids.
• Aurell Maria J., Gavina Pablo, Mestres Ramon, Tetrahedron, 50 (1994) N 8, S 2571-2582
  作者：Aurell Maria J., Gavina Pablo, Mestres Ramon

  DOI：——

  日期：——