8-oxocyclooctene-1-carbonitrile | 634929-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-oxocyclooctene-1-carbonitrile
• CAS: 634929-00-3
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: XAVNEWYDQUQWRZ-UHFFFAOYSA-N

物化性质

• 沸点：
  283.8±30.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  40.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-oxocyclooctene-1-carbonitrile 、 在 zinc(II) chloride 作用下， 反应 1.0h， 以82%的产率得到Ethyl 5-bromo-2-(2-cyano-3-oxocyclooctyl)pentanoate
  参考文献：
  名称：

  K2CO3/NaI-Induced Cyclization of ω-Bromo α-Cyano Ketones: A New Annulation Approach for the Formation of Carbalkoxycyclohexane Ring System

  摘要：

  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.

  DOI：

  10.1055/s-0031-1290386

文献信息

• 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。
• 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.