4,4-Dimethyl-6-oxocyclohexene-1-carbonitrile | 1268673-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4-Dimethyl-6-oxocyclohexene-1-carbonitrile
• 英文别名: 4,4-dimethyl-6-oxocyclohexene-1-carbonitrile
• CAS: 1268673-92-2
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: AVHANSHJUOCUCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 3-oxo-4-pentenoate 、 4,4-Dimethyl-6-oxocyclohexene-1-carbonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以69%的产率得到(4aSR,8aSR)-4a-cyano-2-hydroxy-7,7-dimethyl-5-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  纳扎罗夫试剂与 2-氰基-2-环烯酮的双迈克尔加成反应：顺式稠合双环系统的替代方法

  摘要：

  开发了 2-氰基-2-环烯酮与纳扎罗夫试剂的高度立体选择性环化反应，该反应由 1,8-二氮杂双环 [5.4.0] 十一碳-7-烯 (DBU) 催化，形成密集功能化的双环系统。

  DOI：

  10.1055/s-0033-1340299

文献信息

• Conia-ene annulation of the α-cyano β-TMS-capped alkynyl cycloalkanone system and its synthetic application
  作者：Chih-Lung Chin、Cheng-Feng Liao、Hsing-Jang Liu、Ying-Chieh Wong、Ming-Tsang Hsieh、Prashanth K. Amancha、Chun-Ping Chang、Kak-Shan Shia

  DOI：10.1039/c1ob05591g

  日期：——

  Under catalysis with ZnI2, an effective annulation process of ω-silylacetylenic α-cyano ketones, leading to the formation of various bicyclic frameworks characterized with a TMS-containing methylenecyclopentane ring, has been developed.

  在 ZnI2 的催化下，开发了一种有效的Ï-硅乙炔基δ-±-氰基酮环化过程，从而形成了以含 TMS 的亚甲基环戊烷环为特征的各种双环框架。
• Palladium(ii) acetate mediated oxidative cyclization of ω-unsaturated α-cyano ketones for facile construction of methylenecyclohexane ring system
  作者：Min-Tsang Hsieh、Kak-Shan Shia、Hsing-Jang Liu、Sheng-Chu Kuo

  DOI：10.1039/c2ob25161b

  日期：——

  construction of the structurally attractive methylenecyclohexane ring was developed through a convenient 1,4-addition of 4-pentenylmagnesium bromide to 2-cyano-2-cycloalkenones followed by a Pd(II)-mediated oxidative cyclization of the resulting ω-unsaturated α-cyano ketones. Based on this newly developed protocol, polycyclic adducts bearing various ring sizes and substitutions can be prepared in moderate to

  通过方便的1,4-加成反应，开发了一种高效的环状结构方法，用于构建结构吸引人的亚甲基环己烷环。 4-戊烯基溴化镁生成2-氰基-2-环烯酮，然后经Pd（II）介导的所得ω-不饱和α-氰基酮的氧化环化反应。基于这种新开发的方案，可以以中等至高收率制备带有各种环大小和取代基的多环加合物。
• Autoxidative Annulation Cascade of the α-Cyano β-TMS-capped Alkynyl Cycloalkanone System
  作者：Ying-Chieh Wong、Min-Tsang Hsieh、Prashanth K. Amancha、Chih-Lung Chin、Cheng-Feng Liao、Chun-Wei Kuo、Kak-Shan Shia

  DOI：10.1021/ol102947u

  日期：2011.3.4

  The autoxidative annulation cascade promoted by an a.-cyano beta-TMS-capped alkynyl cycloalkanone system under catalysis with pyridine in one oxygen atmosphere has proven to be highly viable. On the basis of this newly developed protocol, a variety of highly functionalized bicyclic frameworks can be effectively constructed.
• K2CO3/NaI-Induced Cyclization of ω-Bromo α-Cyano Ketones: A New Annulation Approach for the Formation of Carbalkoxycyclohexane Ring System
  作者：Hsing-Jang Liu、Min-Tsang Hsieh、Che-Hao Tu、Kak-Shan Shia、Sheng-Chu Kuo

  DOI：10.1055/s-0031-1290386

  日期：2012.7

  An operationally simple and highly effective annulation process, making use of ZnCl2-catalyzed Michael addition and K2CO3/NaI-induced cyclization as key manipulations, has been developed to construct various bicyclic systems with a high level of functionalization valuable for further synthetic elaboration.
• Double Michael Addition Reactions of the Nazarov Reagent with 2-Cyano-2-Cycloalkenones: An Alternative Approach to cis-Fused Bicyclic Systems
  作者：Hsing-Jang Liu、Min-Tsang Hsieh、Che-Hao Tu、Yen-Ku Wu、Kak-Shan Shia、Sheng-Chu Kuo

  DOI：10.1055/s-0033-1340299

  日期：——

  A highly stereoselective annulation reaction of 2-cyano-2-cycloalkenones with the Nazarov reagent catalyzed by 1,8-diaza­bicyclo[5.4.0]undec-7-ene (DBU), leading to densely functionalized bicyclic systems, is developed.

  开发了 2-氰基-2-环烯酮与纳扎罗夫试剂的高度立体选择性环化反应，该反应由 1,8-二氮杂双环 [5.4.0] 十一碳-7-烯 (DBU) 催化，形成密集功能化的双环系统。