4,5-dimethoxy-2-(p-tolylethynyl)benzaldehyde | 1310569-40-4

• 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: 4,5-dimethoxy-2-(p-tolylethynyl)benzaldehyde
• CAS: 1310569-40-4
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: RUZWYPDGQVQZSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-2-(p-tolylethynyl)benzaldehyde 在 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  由邻炔基苯甲醛和叠氮化三甲基硅一锅合成三唑稠合的异吲哚

  摘要：

  据报道，由邻炔基苯甲醛和三甲基硅烷基叠氮化物（TMSN 3）有效地一锅法合成1,2,3-三唑稠合的异吲哚。该反应通过形成二叠氮化物中间体和随后的分子内叠氮化物-炔烃环加成反应而进行，从而提供了一种新颖的途径来获得各种8-azido-8 H- [1,2,3] triazolo [5,1- a ] isoindoles高产。

  DOI：

  10.1016/j.tetlet.2018.03.002

文献信息

• Efficient Synthesis of Octahydrophenanthrene Derivatives with Mild Cascade Reactions of Isochromenylium Tetrafluoroborates and Bifunctional Styrenes
  作者：Lei Mo、Lin-Lin Wu、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1021/acs.orglett.5b01532

  日期：2015.7.2

  air-stable isochromenylium tetrafluoroborates and bifunctional styrenes containing a 1,3-diketone moiety has been developed, affording the corresponding single diastereomeric ocatahydrophenanthrene derivatives (21 examples, up to 86% yield). A cascade process of [4 + 2]-cyclization and subsequent intramolecular nucleophilic addition is proposed to generate the three new C–C bonds diastereoselectively in

  已经开发了一种高效的无催化剂的空气稳定的四氟硼酸异铬鎓与含有1,3-二酮部分的双官能苯乙烯的级联反应，从而提供了相应的单一非对映异构的ocatahydrophenanthrene菲衍生物（21个实例，产率高达86％）。提出了[4 + 2]-环化和随后的分子内亲核加成的级联过程，以在反应中非对映选择性地产生三个新的CC键。
• Metal-Free Decarboxylative Cyclization/Ring Expansion: Construction of Five-, Six-, and Seven-Membered Heterocycles from 2-Alkynyl Benzaldehydes and Cyclic Amino Acids
  作者：Srinivas Samala、Gajendra Singh、Ravi Kumar、Ravi Sankar Ampapathi、Bijoy Kundu

  DOI：10.1002/anie.201504429

  日期：2015.8.10

  A one pot synthesis of 1H‐benzo[g]indoles, tetrahydrobenzo[h]quinolines, and naphtho[1,2‐b]azepines from 2‐alkynyl benzaldehydes and cyclic amino acids is reported. The salient feature of the strategy involves formation of three new bonds (one CN and two CC bonds) by a metal‐free decarboxylation/cyclization/one‐carbon ring expansion sequence in one pot.

  据报道，由2-炔基苯甲醛和环状氨基酸一锅合成1 H-苯并[g]吲哚，四氢苯并[h]喹啉和萘并[1,2-b]氮杂。该策略的显着特征是通过在一个罐中进行无金属脱羧/环化/一碳环扩环来形成三个新键（一个CN和两个CC键）。
• Access to densely functionalized naphthalenes by organobase catalyzed domino reaction of 2-(2-formylaryl)acetophenones with nitroolefins
  作者：Anuradha Dagar、Soumen Biswas、Shaikh M. Mobin、Sampak Samanta

  DOI：10.1016/j.tetlet.2016.06.062

  日期：2016.7

  A series of new functionalized naphthalene derivatives having carbonyl and NO2 groups at C-1 and C-3 positions respectively have been prepared in good yields (63–75%) through a one-pot domino reaction of several 2-(2-formylaryl)acetophenone derivatives with a variety of aryl/heteroaryl-substituted 2-nitroolefins in EtOH as a green solvent at 75 °C under air using a catalytic amount of DABCO (30 mol %)

  通过一系列2-（2-甲酰基芳基）的一锅多米诺反应，已制备出一系列新的官能化萘衍生物，分别在C-1和C-3位置处具有羰基和NO 2基团。苯乙酮衍生物与各种芳基/杂芳基取代的2-硝基烯烃在EtOH中作为绿色溶剂，在75°C的空气中，使用催化量的DABCO（30 mol％）作为廉价的有机催化剂，作为绿色溶剂。这种经济实惠的过程足够友好，可以保留多种敏感功能，并显示出广泛的基材范围。此外，通过我们的合成方法建立了具有生物吸引力的N-（3-萘基取代的）吡咯骨架的高产率合成。
• Neighbouring Formyl Group Assisted Oxidation of o-Alkynylarenecarbaldehydes by an Iodine/Water System
  作者：Karuppusamy Sakthivel、Kannupal Srinivasan

  DOI：10.1002/ejoc.201001746

  日期：2011.5

  The oxidation of o-alkynylarenecarbaldehydes into tricarbonyl compounds by an iodine/water system is described. The reaction takes place via isochromenol intermediates formed by intramolecular assistance of the formyl group. The procedure was applied to various o-alkynylarenecarbaldehydes to afford the corresponding products in good to excellent yields.

  描述了通过碘/水系统将邻炔基芳烃甲醛氧化成三羰基化合物。该反应通过由甲酰基的分子内辅助形成的异色烯醇中间体发生。该程序应用于各种邻炔基芳烃甲醛，以良好到极好的收率提供相应的产品。
• Asymmetric Cascade Annulation Based on Enantioselective Oxa-Diels–Alder Cycloaddition of in Situ Generated Isochromenyliums by Cooperative Binary Catalysis of Pd(OAc)₂ and (<i>S</i>)-Trip
  作者：Shu-Yan Yu、Hao Zhang、Yang Gao、Lei Mo、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1021/ja405764p

  日期：2013.7.31

  An asymmetric cascade annulation between 2-hydroxystyrenes and 2-alkynylbenaldehyes or 1-(2-alkynylphenyl)ketones has been established with good to excellent enantioselectivities (up to >99.5% ee), on the basis of an enantioselective oxa-Diels-Alder cycloaddition of in situ generated metallo-isochromenylium intermediates, by cooperative binary catalysis of Pd(OAc)(2) and (S)-Trip. The developed methodology is workable for a broad spectrum of substrates and shows great efficiency in establishing dense multiple chiral centers including quaternary carbons of variable bridged ring systems. The mechanism study suggests that (S)-Trip plays multiple roles in assembling the reactants and controlling the stereoselectivity.