5,5-dimethyl-3-(2-phenylethynyl)cyclohex-2-enone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-dimethyl-3-(2-phenylethynyl)cyclohex-2-enone
• 英文别名: 5,5-dimethyl-3-(phenylethynyl)cyclohex-2-enone；3-(2-phenylethynyl)-5,5-dimethylcyclohex-2-enone；5,5-Dimethyl-3-(2-phenylethynyl)cyclohex-2-en-1-one；5,5-dimethyl-3-(2-phenylethynyl)cyclohex-2-en-1-one
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: BMLRUUXGLLLNKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-3-(2-phenylethynyl)cyclohex-2-enone 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以56%的产率得到5,5-dimethyl-3-(5-phenyl-2H-triazol-4-yl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Design, Synthesis, and Diversification of 3,5-Substituted Enone Library

  摘要：

  This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloacklition sequence. The library was analyzed by principal component analysis to examine its diversity.

  DOI：

  10.1021/co200070m
• 作为产物：
  描述：

  3-碘-5,5-二甲基环己-2-烯-1-酮 在 sodium tetrahydroborate 、 正丁基锂 、 对甲苯磺酸 、 溶剂黄146 作用下， 反应 18.0h， 生成 5,5-dimethyl-3-(2-phenylethynyl)cyclohex-2-enone
  参考文献：
  名称：

  有机硒化合物上的羰基转座

  摘要：

  羰基共轭乙烯基硒化物通过有机金属试剂加成反应进行1,3和1,5-羰基转座序列，然后进行酸水解。

  DOI：

  10.1016/s0040-4020(97)00454-7

文献信息

• Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Alkenyl Tosylates for the Synthesis of Enynones
  作者：Subeen Yu、Eunjeong Cho、Jimin Kim、Sunwoo Lee

  DOI：10.1021/acs.joc.7b02175

  日期：2017.10.20

  A palladium-catalyzed decarboxylative coupling reaction was developed for the synthesis of 3-(1-alkynyl)-2-cyclohexen-1-ones. A variety of alkynyl carboxylic acids were coupled with 3-oxocyclohexenyl tosylates to afford the corresponding enynones in good to excellent yields. The developed catalytic system is phosphine free and showed good tolerance toward various functionalities such as chloride, cyano

  开发了钯催化的脱羧偶联反应，用于合成3-（1-炔基）-2-环己烯-1-酮。将各种炔基羧酸与3-氧代环己烯基甲苯磺酸酯偶联，以良好至优异的产率提供相应的烯酮。先进的催化体系不含膦，对各种功能（如氯，氰基，硝基，酯，醛和醇基）表现出良好的耐受性。另外，与丙炔基甲苯磺酸酯的反应中，苯基丙酸比苯基乙炔表现出更高的反应性。
• Photocycloaddition of Conjugated Cyclohex-2-enones to 2,3-Dimethylbuta-1,3-diene
  作者：Inga Inhülsen、Kerstin Schmidt、Paul Margaretha

  DOI：10.1002/hlca.201000042

  日期：——

  3 and 4, whereas, under these conditions, 3‐(alk‐1‐ynyl)cyclohex‐2‐enones 5 give only one cyclobutane adduct 6 regio‐ and diastereoselectively. In contrast, 3‐(alk‐1‐ynyl)‐2‐methylcyclohex‐2‐enones 10 undergo [2+2]‐cycloaddition to the same diene exclusively at the C≡C bond to afford hitherto unknown 3‐cyclobutenylcyclohex‐2‐enones 11.

  上照射，在2,3-二甲基丁-1,3-二烯的存在下，萘-2-酮1是定量和区域选择性转化成非对映异构环丁烷加合物的混合物3和4，而在这些条件下，3-（烷基-1-炔基）环己-2-烯酮5仅选择性地产生一个环丁烷和非对映体的环丁烷加合物6。相反，3-（alk-1-ynyl）-2-methylcyclohex-2-enones 10仅在C≡C键上与同一二烯进行[2 + 2]-环加成反应，从而提供迄今未知的3-cyclobutenylcyclohex-2-烯酮11。
• The coupling of butylvinyltellurides with organometallic reagents catalysed by nickel complexes
  作者：Cristiano Raminelli、João Gargalaka、Cláudio C. Silveira、João V. Comasseto

  DOI：10.1016/j.tet.2007.06.057

  日期：2007.9

  Vinylic tellurides couple efficiently with sp, sp(2) and sp(3) hybridised organometallic compounds (Li, MgX and Zn species) in the presence of dichloro-bis( triphenylphosphine) nickel(II) as catalyst. (c) 2007 Elsevier Ltd. All rights reserved.
• Carbonyl transposition on organoselenium compounds
  作者：João V. Comasseto、Wai L. Lo、Nicola Petragnani

  DOI：10.1016/s0040-4020(97)00454-7

  日期：1997.6

  Carbonyl conjugated vinylic selenides undergo 1,3 and 1,5-carbonyl transposition sequences through organometallic reagents addition reactions followed by acid hydrolysis.

  羰基共轭乙烯基硒化物通过有机金属试剂加成反应进行1,3和1,5-羰基转座序列，然后进行酸水解。
• Design, Synthesis, and Diversification of 3,5-Substituted Enone Library
  作者：Juhienah Khalaf、Maria E. Estrella-Jimenez、Matthew J. Shashack、Sharangdhar S. Phatak、Shuxing Zhang、Scott R. Gilbertson

  DOI：10.1021/co200070m

  日期：2011.7.11

  This paper describes the synthesis of a 300 member library of 3,5-substituted enones. The synthesis starts with 6 different bromoenones that are accessed from the corresponding 1,3 diones. These bromides are then diversified by Suzuki coupling with a variety of aromatic and vinyl boronic acids. Additionally a small series of triazoles was synthesized by a Sonogashira coupling reaction dipolar cycloacklition sequence. The library was analyzed by principal component analysis to examine its diversity.