3-phenyl-2-nonen-4-ynal | 104429-45-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3-phenyl-2-nonen-4-ynal
• 英文别名: (Z)-3-phenylnon-2-en-4-ynal
• CAS: 104429-45-0
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: KRKYCYXTTHCYHK-NTCAYCPXSA-N

物化性质

• 沸点：
  343.6±31.0 °C(Predicted)
• 密度：
  0.994±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  3-phenyl-2-nonen-4-ynal 在 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 2-[(E)-2-methoxyhept-2-en-3-yl]-1-methylsulfonyl-3-phenylpyrrole
  参考文献：
  名称：

  Synthesis of Pyrroles through Coupling of Enyne-hydrazones with Fischer Carbene Complexes

  摘要：

  The coupling of enyne-imines with Fischer carbene complexes leads to the formation of alkenylpyrrole derivatives. Maximum yields of pyrrole adducts were obtained using N,N-dimethylhydrazones. A mechanism involving alkyne insertion followed by nucleophilic attack of the imine nitrogen at the intermediate alkenylcarbene complex was proposed.

  DOI：

  10.1021/ol034414j
• 作为产物：
  描述：

  (E)-beta-氯丙烯酰苯 在 乙醇 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 3-phenyl-2-nonen-4-ynal
  参考文献：
  名称：

  Eberbach, Wolfgang; Roser, Joachim, Heterocycles, 1985, vol. 23, # 11, p. 2797 - 2802

  摘要：

  DOI：

文献信息

• One‐Pot Tandem Catalysis: A Concise Route to Fused Bicyclic Scaffolds from Acyclic β‐Ketoesters and Alkynyl Aldehydes
  作者：Lu Liu、Lai Wei、Yong Lu、Junliang Zhang

  DOI：10.1002/chem.201001729

  日期：2010.10.18

  rapid and highly efficient route to fused polycyclic scaffolds from simple, readily available β‐ketoesters and alkynyl aldehydes was developed (see scheme) as a one‐pot reaction by combining three fundamental reactions, that is, the Knoevenagel condensation, Nazarov cyclization, and Conia‐ene reactions. Piperidinium acetate was found to be a tandem catalyst in these one‐pot reactions.

  “快速”合成：通过结合三个基本反应，即一锅反应，开发了一种快速，高效的方法，从简单易得的β-酮酸酯和炔醛制得稠合多环支架（见方案）。 Knoevenagel缩合，Nazarov环化和Conia-ene反应。发现乙酸哌啶是这些一锅法反应中的串联催化剂。
• Intramolecular Carboxyamidation of Alkyne‐Tethered <i>O</i>‐Acylhydroxamates through Formation of Fe(III)‐Nitrenoids
  作者：Siyuan Su、Yu Zhang、Peng Liu、Donald J. Wink、Daesung Lee

  DOI：10.1002/chem.202303428

  日期：2024.1.26

  induced spontaneous or 4-(dimethylamino)pyridine-catalyzed O→O or O→N acyl group migration can generate a wide variety of N,O-containing heterocycles. DFT study suggests the Fe-nitrenoid intermediate preferentially reacts in a radical manifold to mediates a stepwise C−N/C−O bond formation rather than a concerted [3+2] cycloaddition mechanism.

  Zip and shift : 炔烃束缚的O-酰基异羟肟酸酯的分子内羧酰胺化，然后是热诱导自发或4-(二甲氨基)吡啶催化的O→O或O→N酰基迁移，可以生成多种含N 、 O的杂环。 DFT 研究表明，Fe-氮烯类中间体优先在自由基流形中反应，介导逐步的 C−N/C−O 键形成，而不是协调一致的 [3+2] 环加成机制。
• Palladium-Catalyzed Alkoxycarbonylation of (<i>Z</i>)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates
  作者：G. Eray Akpınar、Melih Kuş、Muhammed Üçüncü、Erman Karakuş、Levent Artok

  DOI：10.1021/ol102989q

  日期：2011.2.18

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.
• Synthesis of Furan-Bridged 10-Membered Rings through [8 + 2]-Cycloaddition of Dienylfurans and Acetylenic Esters
  作者：Lei Zhang、Yu Wang、Clare Buckingham、James W. Herndon

  DOI：10.1021/ol050416n

  日期：2005.4.14

  The coupling of various dienylfurans with dimethyl acetylenedicarboxylate (DMAD) has been examined. In most cases this reaction proceeds via [8 + 2]-cycloaddition to afford furan-bridged 10-membered ring systems as a single diastereomer. Dienylfuran intermediates were generated using either a chromium carbene-based method or aldol-based methods. Reaction of [8 + 2]-cycloadducts with electrophilic reagents occurred selectively at the enol ether alkene.
• Synthesis of Pyrroles through Coupling of Enyne-hydrazones with Fischer Carbene Complexes
  作者：Yanshi Zhang、James W. Herndon

  DOI：10.1021/ol034414j

  日期：2003.6.1

  The coupling of enyne-imines with Fischer carbene complexes leads to the formation of alkenylpyrrole derivatives. Maximum yields of pyrrole adducts were obtained using N,N-dimethylhydrazones. A mechanism involving alkyne insertion followed by nucleophilic attack of the imine nitrogen at the intermediate alkenylcarbene complex was proposed.