(E)-5-cyclononen-1-one | 52920-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-cyclononen-1-one
• 英文别名: E-cyclonon-5-enone；(E)-cyclonon-5-en-1-one；(5E)-cyclonon-5-en-1-one；(E)-1-Cyclononene-6-one
• CAS: 52920-64-6
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: QKGZGNQTMCUFOI-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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)-5-cyclononen-1-one 在 Porcine pancreatic lipase type II 、 potassium hydride 作用下， 以 乙二醇二甲醚 、 正己烷 为溶剂， 反应 1.0h， 生成 (-)-(1E,5E)-cyclonona-1,5-dien-1-yl acetate
  参考文献：
  名称：

  Dynamic Chirality of (E)-5-Cyclononen-1-one and its Enolate

  摘要：

  It has been found that (E)-5-cyclononen-1-one (2a) exhibits marginal planar chirality owing to an insufficient topological constraint, whereas the enolates 3 derived from 2a show robust planar chirality. Enantioenriched enolates are easily prepared by enzymatic hydrolysis, and they show an ability to serve as chiral nucleophiles.

  DOI：

  10.1021/ja1092375
• 作为产物：
  描述：

  2-氯环戊酮 在 potassium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (E)-5-cyclononen-1-one
  参考文献：
  名称：

  Dynamic Chirality of (E)-5-Cyclononen-1-one and its Enolate

  摘要：

  It has been found that (E)-5-cyclononen-1-one (2a) exhibits marginal planar chirality owing to an insufficient topological constraint, whereas the enolates 3 derived from 2a show robust planar chirality. Enantioenriched enolates are easily prepared by enzymatic hydrolysis, and they show an ability to serve as chiral nucleophiles.

  DOI：

  10.1021/ja1092375

文献信息

• The Pauson–Khand reaction of medium sized trans-cycloalkenes
  作者：Agustí Lledó、Aida Fuster、Marc Revés、Xavier Verdaguer、Antoni Riera

  DOI：10.1039/c3cc41005f

  日期：——

  Medium sized trans-cycloalkenes are unusually reactive in the intermolecular Pauson-Khand reaction (PKR) with regard to typical monocyclic alkenes. This is due to the ring strain imparted by the E stereochemistry. The PKR of these alkenes offers a modular, regioselective and straightforward entry to trans fused [n.3.0] bicyclic scaffolds (n = 6-8).

  就典型的单环烯烃而言，中型反式环烯烃在分子间Pauson-Khand反应（PKR）中具有异常的反应性。这是由于E立体化学赋予的环应变。这些烯烃的PKR为反式[n.3.0]双环支架（n = 6-8）提供了模块化，区域选择性和直接进入的途径。
• Synthesis and Stereochemical Behavior of (<i>E</i>)-Cyclononene Derivatives
  作者：Katsuhiko Tomooka、Hiroko Inoue、Kazunobu Igawa

  DOI：10.1246/cl.2011.591

  日期：2011.6.5

  A versatile synthetic approach to planar chiral molecules from (E)-5-cyclononen-1-one (1) has been developed; these molecules have multifunctionalities with (E)-cyclononene skeleton. The newly synthesized keto-ester 3 having central chirality shows labile planar chirality. In contrast, enol derivative 4 and enyne 5 show robust planar chirality.

  从 (E)-5-cyclonen-1-one (1) 到平面手性分子的多功能合成方法已经开发出来；这些分子具有(E)-环壬烯骨架的多功能性。新合成的酮酯 3 具有中心手性，显示出易变的平面手性。相比之下，烯醇衍生物 4 和炔类化合物 5 则表现出强劲的平面手性。
• A Facile Synthesis of 1,2-Divinylcycloalkanols and Their Behavior in the Oxy-Cope Rearrangement
  作者：Tetsuya Kato、Hisao Kondo、Masaki Nishino、Minoru Tanaka、Go Hata、Akihisa Miyake

  DOI：10.1246/bcsj.53.2958

  日期：1980.10

  2-chlorocycloalkanones with vinylmagnesium chloride gives 1,2-divinylcycloalkanols. Divinylation proceeds via a rearrangement of initially formed 2-chloro-1-vinylcycloalkanols to 2-vinylcycloalkanones followed by further vinylation of 2-vinylcycloalkanones. Thermal sigmatropic rearrangement of 1,2-divinylcycloalkanols gives 5-cycloalken-1-ones in good yields. The influence of the size of rings on the

  2-氯环烷酮与乙烯基氯化镁反应生成1,2-二乙烯基环烷醇。二乙烯基化通过最初形成的 2-氯-1-乙烯基环烷醇重排为 2-乙烯基环烷酮，然后 2-乙烯基环烷酮的进一步乙烯基化而进行。1,2-二乙烯基环烷醇的热sigmatropic重排以良好的产率得到5-环烯-1-酮。讨论了环的大小对反应途径的影响。
• Carbocyclic ring expansion reactiuon VIA radical chain processes
  作者：Jack E. Baldwin、Robert M. Adlington、Jeremy Robertson

  DOI：10.1016/0040-4020(89)80003-1

  日期：1989.1
• Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes
  作者：Andrew S. Kende、Clara E. Mota Nelson、Sébastien Fuchs

  DOI：10.1016/j.tetlet.2005.09.125

  日期：2005.11

  Medium-ring olefinic ketone and lactone enolsilanes were subjected to palladium(II)-mediated cycloalkenylation conditions. Diverse bicyclic ring products were obtained in moderate to good yields. The effect of olefin geometry and ring size is discussed. (c) 2005 Elsevier Ltd. All rights reserved.