3-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde | 1224712-71-3

• 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: 3-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde
• 英文别名: 3-methoxy 2-(3-phenyl-prop-2-ynyloxy)-benzaldehyde；3-Methoxy-2-(3-phenylprop-2-ynoxy)benzaldehyde
• CAS: 1224712-71-3
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: AXUCLBMXWVJBEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde 在 哌啶 、 sodium hydride 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 dimethyl 2-(3-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)phenyl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Lewis酸催化的环丙烷1,1-二酯与炔烃的分子内[3 + 2]环加成反应，合成环戊[c]苯甲基骨架

  摘要：

  提出了一种有效的方法，该方法通过路易斯酸催化的环丙烷1,1-二酯的分子内[3 + 2]环加成炔与环炔构筑环戊[ c ]色烯骨架。可以在一个步骤中以中等至极好的产率（高达94％）形成两个新的熔合循环，并且可以在简单的反应条件下将产物转化为具有生物活性的巴比妥酸衍生物（1）。

  DOI：

  10.1002/asia.201200104
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 三溴化磷 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 3-methoxy-2-((3-phenylprop-2-yn-1-yl)oxy)benzaldehyde
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of Functionalized 2H-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis

  摘要：

  An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, brow, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.

  DOI：

  10.1021/jo2000012

文献信息

• N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes
  作者：Akkattu T. Biju、Nathalie E. Wurz、Frank Glorius

  DOI：10.1021/ja102130s

  日期：2010.5.5

  The N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated alkynes to provide alpha,beta-unsaturated ketones is reported. In addition, a rare case of an efficient and selective dually NHC-catalyzed cascade reaction involving the hydroacylation of alkynes and a subsequent intermolecular Stetter reaction allows the formation of chromanones containing a 1,4-diketone moiety.

  报道了 N-杂环卡宾 (NHC) 催化的未活化炔烃的加氢酰化，以提供 α、β-不饱和酮。此外，涉及炔烃加氢酰化和随后的分子间 Stetter 反应的高效和选择性双重 NHC 催化级联反应的罕见情况允许形成含有 1,4-二酮部分的色满酮。
• NHC‐Stabilized Radicals in the Formal Hydroacylation Reaction of Alkynes
  作者：Jenny Phan、Stephanie‐M. Ruser、Kirsten Zeitler、Julia Rehbein

  DOI：10.1002/ejoc.201801185

  日期：2019.1.23

  Mechanistic details of transformations catalyzed by N‐heterocyclic carbenes (NHC) are currently of great interest, targeting questions on the active catalyst in operation and the structure and reactivity of key intermediates. These mechanistic studies are driven by the need to understand the big impact of subtle changes on the catalyst system on its reactivity, as well as to clarify the situation around

  目前，正受到N-杂环卡宾（NHC）催化的转化机理的详细研究，针对操作中的活性催化剂以及关键中间体的结构和反应性提出了疑问。这些机理研究的动力是需要了解催化剂体系的细微变化对其反应性的巨大影响，以及阐明经典催化循环中难以捉摸的中间体的情况。在醛的活化过程中，被广泛称为布雷斯洛中间体的烯胺结构的形成被广泛接受。但是，以前我们可以证明，该烯醇除了通过其离子反应途径外，还可以通过与起始原料一起进行氧化还原过程来遵循自由基途径。在本研究中，我们旨在阐明这些自由基途径是否是更普遍的现象，特别是在炔烃的正式加氢酰化反应中。自由基种类的观察以及自由基和离子途径中关键元素步骤的计算分析可能会导致基于NHC稳定碳自由基的化学的进一步发展。
• Boron trifluoride–etherate in fluorinated alcohols: A powerful promoter system for intramolecular alkyne–aldehyde metathesis of o-(3-arylpropargyloxy)benzaldehydes
  作者：Arup Jyoti Das、Runjun Devi、Sajal Kumar Das

  DOI：10.1016/j.tetlet.2018.10.040

  日期：2018.11

  Boron trifluoride-etherate (BF3 center dot OEt2) in 2,2,2-trifluoroethanol (TFE) was found to be a highly efficient promoter system for the intramolecular alkyne-aldehyde metathesis of o-(3-arylpropargyloxy)benzaldehydes. The reaction produces the corresponding 3-aroyl-2H-chromenes in excellent yields under metal free conditions. (C) 2018 Elsevier Ltd. All rights reserved.
• Iron-Catalyzed Synthesis of Functionalized 2<i>H</i>-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis
  作者：Krishnendu Bera、Soumen Sarkar、Srijit Biswas、Sukhendu Maiti、Umasish Jana

  DOI：10.1021/jo2000012

  日期：2011.5.6

  An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, brow, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.
• Lewis Acid‐Catalyzed Intramolecular [3+2] Cycloaddition of Cyclopropane 1,1‐Diesters with Alkynes for the Synthesis of Cyclopenta[ <i>c</i> ]chromene Skeletons
  作者：Xiao‐Feng Xia、Xian‐Rong Song、Xue‐Yuan Liu、Yong‐Min Liang

  DOI：10.1002/asia.201200104

  日期：2012.7

  An efficient method to construct cyclopenta[c]chromene skeletons by Lewis acid‐catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1‐diesters with alkynes is presented. Two new fused cycles can be formed in one step in moderate to excellent yields (up to 94 %), and the products can be converted into bioactive barbituric acid derivatives (1) under simple reaction conditions.

  提出了一种有效的方法，该方法通过路易斯酸催化的环丙烷1,1-二酯的分子内[3 + 2]环加成炔与环炔构筑环戊[ c ]色烯骨架。可以在一个步骤中以中等至极好的产率（高达94％）形成两个新的熔合循环，并且可以在简单的反应条件下将产物转化为具有生物活性的巴比妥酸衍生物（1）。