(E)/(Z)-cycloundec-2-enone | 115025-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)/(Z)-cycloundec-2-enone
• 英文别名: Cycloundec-2-enone；2-cycloundecenone；Cycloundec-2-en-1-one；cycloundec-2-en-1-one
• CAS: 115025-16-6
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: GYCVSJRJXSPDOH-UHFFFAOYSA-N

物化性质

• 沸点：
  272.2±10.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (E)/(Z)-cycloundec-2-enone 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 116.0h， 生成 12-Chloro-17-azatricyclo[8.7.1.011,16]octadeca-1(17),10(18),11(16)-triene
  参考文献：
  名称：

  关于（乙烯基乙烯基）磷光烷与相关化合物的反应。[ n ]（2,4）吡啶并[[ n ]（2,4）喹啉甲烷（n = 9–7）的新颖合成和性质

  摘要：

  [ n ]（2,4）pyridinophanes 13a–c（n  = 9–7）和14a–c（n  = 9–7）以及15a（n  = 9）和16a（n  ＝ 9）由3-氨基环己-2-烯酮和几种β-氨基烯酮与环烷-2-烯酮在烯胺-烷基化过程中的反应，随后的氨基与羰基官能团的缩合以及产物的脱氢组成在脱氢剂（10％Pd / C）存在下。具有喹啉骨架的环己烯酮环化的[ n ]（2,4）吡啶并吡啶13a–c可方便地转化为一系列[ n ]（2,4）喹啉并烷26a–c（n  = 9–7），包括已知的[8]（2,4）喹啉oph烷26b。在各种温度下的1 H NMR光谱证实了[7]（2,4）吡啶并[13]，14c和[7]（2,4）喹啉基环烷26c的七亚甲基链的动力学行为。桥翻转的能垒（ ΔG ‡ c）对于13c为11.3 kcal mol –1（ T c –10°C），对于14c为11.7 kcal mol

  DOI：

  10.1039/a904790e

文献信息

• Novel synthesis, static and dynamic properties, and structural characteristics of 5-cyano[n](2,4)pyridinophane-6-ones (n = 9–6) and their chemical transformations
  作者：Makoto Nitta、Tsuyoshi Sakakida、Hideo Miyabara、Hiroyuki Yamamoto、Shin-ichi Naya

  DOI：10.1039/b416013d

  日期：——

  chains for [7](2,4)- and [6](2,4)pyridinophane-6-one derivatives 12c and 12d. The energy barrier (Delta G(++)) of the bridge flipping of 12c is estimated to be 12.0 kcal mol(-1)(T(c)= 0 degree C). On the other hand, compound 12d undergoes pseudorotation (conformational change of the methylene chain) at room temperature, and does not undergo bridge flipping even at 150 degree C in DMSO-d(6). The energy

  5-氰基[n]（2,4）吡啶啉-6-酮12a-d（n = 9、8、7和6）的新颖合成包括使氰基乙酰胺与环烷-2-烯酮反应。根据其光谱性质，循环伏安法和理论计算，研究了它们的静态和动态特性以及结构特性。在不同温度下的（1）H和（13）C NMR光谱已阐明[7]（2,4）-和[6]（2,4）吡啶并-6-6衍生物12c的亚甲基链的动力学行为。和12d。12c的桥翻转的能垒（Delta G（++））估计为12.0 kcal mol（-1）（T（c）= 0摄氏度）。另一方面，化合物12d在室温下进行假旋转（亚甲基链的构象变化），并且即使在DMSO-d（6）中在150℃下也不发生桥翻转。发现亚甲基链12d的假旋转的能垒（Delta G（++））为10.5 kcal mol（-1）（T（c）=-25摄氏度），因此有两个稳定构象的如理论计算所预测的那样确定12d的六亚甲基桥。还通过X射线晶体学分析确定12
• On the Reactions of (Vinylimino)phosphoranes and Related Compounds. 27. A Short New Synthesis of Azuleno[2,1-b]pyridines and Azuleno-Annulated [n](2,4)Pyridinophanes
  作者：Makoto Nitta、Takuya Akie、Yukio Iino

  DOI：10.1021/jo00085a018

  日期：1994.3

  A short new synthesis of azuleno[2,1-b]pyridines 6a-g consists of the reaction of 2-aminoazulene (4) with acyclic alpha,beta-unsaturated ketones and aldehydes in an enamine-alkylation process, subsequent condensation of the amino group with a carbonyl function, and dehydrogenation in the presence of Pd/C. Similarly, the reaction of 4 with alpha,beta-unsaturated cycloalkenones gives azuleno-annulated [n](2,4)pyridinophanes 12a-c (n = 9-7) and dihydrogenated analogue 11d (n = 6). Compound 11d is converted to azuleno-annulated [6](2,5)pyridinophane 12d by treatment with DDQ. H-1 NMR spectroscopy at various temperatures shows dynamic behavior for the oligomethylene chains of [7]- and [6](2,4)pyridinophanes 12c,d. The energy barriers (DELTAG(c)double dagger) for the bridge flipping are 10.8 kcal/mol (T(c), -30-degrees-C) for 12c and 18.1 kcal/mol (T(c), 90-degrees-C) for 12d. Although the strain of 12c,d increases as the chainlength becomes shorter, the pyridine ring of 12c,d can flex more easily than that of the corresponding unannulated [n] (2,4)pyridinophanes. The deformation of the pyridine ring of 12a-d is also suggested by red shifts of the UV and H-1 NMR spectra. The pK(a) values of 12a-d are independent of the size of the methylene bridge, suggesting that the energy differences between the protonated and nonprotonated forms are almost the same for 12a-d.
• Is pseudorotation the operational pathway for bond shifting within [8]annulenes? Probe of planarization requirements by 1,3-annulation of the cyclooctatetraene ring. Kinetic analysis of racemization and 2-D NMR quantitation of .pi.-bond alternation and ring inversion as a function of polymethylene chain length
  作者：Leo A. Paquette、Ting Zhong Wang、Jihmei Luo、Charles E. Cottrell、Amy E. Clough、Larry B. Anderson

  DOI：10.1021/ja00157a038

  日期：1990.1
• Studies on Pyrimidine-annulated Heterocycles: Synthesis and Dynamic Properties of [n](2,4)Pyridinophanes (n = 11, 9, 8, 6)
  作者：Makoto Nitta、Hiroyuki Yamamoto、Hidekazu Takeda

  DOI：10.3987/com-00-8895

  日期：——
• Kanomata, Nobuhiro; Nitta, Makoto, Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1119 - 1126
  作者：Kanomata, Nobuhiro、Nitta, Makoto

  DOI：——

  日期：——