4-methyl-5-phenylpent-2,4-dienal | 86395-64-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methyl-5-phenylpent-2,4-dienal
• 英文别名: 4-methyl-5-phenylpenta-2,4-dienal；4-Methyl-5-phenyl-2,4-pentadienal
• CAS: 86395-64-4
• 化学式: C₁₂H₁₂O
• 分子量: 172.227
• InChiKey: NMMYKIHZWBNDFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 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-甲基-1-乙酰基-1H-吲哚 、 4-methyl-5-phenylpent-2,4-dienal 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以45%的产率得到
  参考文献：
  名称：

  Iron-Mediated Domino Interrupted Iso-Nazarov/Dearomative (3 + 2)-Cycloaddition of Electrophilic Indoles

  摘要：

  An efficient domino reaction combining different classes of pericyclic reactions leads to chiral complex polycyclic indoline-based architectures from achiral starting materials under mild conditions. This practical method is based on the ability of iron(III) chloride to promote both 4 pi electrocyclizations of 2,4-dienals and the C2-C3 umpolung of N-acetylindoles during the dearomative (3 + 2) cycloadditions.

  DOI：

  10.1021/acs.orglett.6b02613

文献信息

• Copper and Rhodium Relay Catalysis for Selective Access to <i>cis</i>-2,3-Dihydroazepines
  作者：You Li、Han Luo、Zongyuan Tang、Yingzi Li、Luan Du、Xiaolan Xin、Shanshan Li、Baosheng Li

  DOI：10.1021/acs.orglett.1c02262

  日期：2021.8.20

  access synthetically challenging cis-2,3-dihydroazepines is reported. The reaction starts with readily available dienals, alkynes, and sulfonyl azides as the substrates and employs copper and rhodium as relay catalysts. Key steps include a copper-catalyzed reaction between an alkyne and a sulfonyl azide to form a triazole intermediate. The subsequent activation of this triazole intermediate by a rhodium

  报告了一种新的催化协议，用于访问具有合成挑战性的顺式-2,3-二氢氮杂。该反应以容易获得的二烯醛、炔烃和磺酰叠氮化物作为底物开始，并使用铜和铑作为中继催化剂。关键步骤包括炔烃和磺酰叠氮化物之间的铜催化反应，以形成三唑中间体。随后用铑催化剂活化该三唑中间体，随后与二烯醛底物反应，最终产生二氢氮杂产物。产品的区域和立体化学被认为是通过立体定向旋转 8π-电环化过程来控制的，以对抗可能的竞争性 6π-电环化过程。
• Cycloisomerization of Conjugated Trienones and Isomeric 2<i>H</i>-Pyrans: Unified Strategy toward Cyclopenta[<i>b</i>]furans
  作者：Martín J. Riveira、Gastón N. Quiroga、Ernesto G. Mata、Vincent Gandon、Mirta P. Mischne

  DOI：10.1021/acs.joc.5b00818

  日期：2015.6.19

  Conjugated trienones and isomeric 2H-pyrans were found to engage in a novel cycloisomerization cascade toward cyclopenta[b]furan derivatives. Knoevenagel chemistry and pericyclic reactions meet again to expand the polyene-carbonyl manifold.
• In Situ Generation of Cyclopentadienol Intermediates from 2,4-Dienals. Application to the Synthesis of Spirooxindoles via a Domino Polycyclization
  作者：Anne-Sophie Marques、Jérôme Marrot、Isabelle Chataigner、Vincent Coeffard、Guillaume Vincent、Xavier Moreau

  DOI：10.1021/acs.orglett.7b03934

  日期：2018.2.2

  An efficient domino polycyclization combining different classes of pericyclic reactions leads to complex spiroxindoles under mild conditions. This domino process represents a rare example of an in situ formation of cyclopentadienol derivatives from an interrupted iso-Nazarov electrocyclization of 2,4-dienals and their use in [4 + 2] cycloaddition reactions. According to the reaction conditions, different polycyclic architectures are obtained in good yields and excellent diastereoselectivities.