4,5-dimethoxy-2-(oct-1-ynyl)benzaldehyde | 928833-54-9

• 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-(oct-1-ynyl)benzaldehyde
• 英文别名: 4,5-Dimethoxy-2-oct-1-ynylbenzaldehyde
• CAS: 928833-54-9
• 化学式: C₁₇H₂₂O₃
• 分子量: 274.36
• InChiKey: WVICITHMKYXHHA-UHFFFAOYSA-N

物化性质

• 熔点：
  43-46 °C
• 沸点：
  418.5±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  4,5-dimethoxy-2-(oct-1-ynyl)benzaldehyde 在 水 、 silver trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以71%的产率得到2-(1-(3-hexyl-6,7-dimethoxy-1H-isochromen-1-yl)-2-oxooctyl)-4,5-dimethoxybenzaldehyde
  参考文献：
  名称：

  Discovery of Chemical Reactions through Multidimensional Screening

  摘要：

  Multidimensional reaction screening of ortho-alkynyl benzaldehydes with a variety of catalysts and reaction partners was conducted in an effort to identify new chemical reactions. Reactions affording unique products were selected for investigation of preliminary scope and limitations.

  DOI：

  10.1021/ja0674744
• 作为产物：
  描述：

  1-辛炔 、 6-溴藜芦醛 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以81%的产率得到4,5-dimethoxy-2-(oct-1-ynyl)benzaldehyde
  参考文献：
  名称：

  Discovery of Chemical Reactions through Multidimensional Screening

  摘要：

  Multidimensional reaction screening of ortho-alkynyl benzaldehydes with a variety of catalysts and reaction partners was conducted in an effort to identify new chemical reactions. Reactions affording unique products were selected for investigation of preliminary scope and limitations.

  DOI：

  10.1021/ja0674744

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）。
• Discovery of new antimalarial chemotypes through chemical methodology and library development
  作者：Lauren E. Brown、Ken Chih-Chien Cheng、Wan-Guo Wei、Pingwei Yuan、Peng Dai、Richard Trilles、Feng Ni、Jing Yuan、Ryan MacArthur、Rajarshi Guha、Ronald L. Johnson、Xin-zhuan Su、Melissa M. Dominguez、John K. Snyder、Aaron B. Beeler、Scott E. Schaus、James Inglese、John A. Porco

  DOI：10.1073/pnas.1017666108

  日期：2011.4.26

  In an effort to expand the stereochemical and structural complexity of chemical libraries used in drug discovery, the Center for Chemical Methodology and Library Development at Boston University has established an infrastructure to translate methodologies accessing diverse chemotypes into arrayed libraries for biological evaluation. In a collaborative effort, the NIH Chemical Genomics Center determined IC ₅₀ ’s for Plasmodium falciparum viability for each of 2,070 members of the CMLD-BU compound collection using quantitative high-throughput screening across five parasite lines of distinct geographic origin. Three compound classes displaying either differential or comprehensive antimalarial activity across the lines were identified, and the nascent structure activity relationships (SAR) from this experiment used to initiate optimization of these chemotypes for further development.

  为了扩展药物发现中使用的化学文库的立体化学和结构复杂性，波士顿大学化学方法和文库发展中心建立了一个基础设施，用于将访问多样化化学类型的方法转化为用于生物评估的排列文库。在合作努力中，美国国立卫生研究院化学基因组中心确定了CMLD-BU化合物收藏中2,070个成员对疟原虫的IC₅₀活性，使用定量高通量筛选跨越五种不同地理起源的寄生虫系列。识别出三种化合物类别，在这些系列中显示出不同或综合的抗疟疾活性，并利用这次实验的初生结构活性关系（SAR）来启动这些化学类别的优化，以进一步发展。
• Synthesis of Pyrrolo-isoquinolines Related to the Lamellarins Using Silver-Catalyzed Cycloisomerization/Dipolar Cycloaddition
  作者：Shun Su、John A. Porco

  DOI：10.1021/ja072737v

  日期：2007.6.1

  Synthesis of pyrrolo-isoquinolines related to the lamellarin alkaloids employing silver-catalyzed cycloisomerization−dipolar cycloaddition of alkynyl N-benzylidene glycinates is described. Mechanistic studies revealed Ag(I)-catalyzed cycloisomerization to an azomethine ylide as a key step for formation of angular pyrrolo-isoquinolines.

  描述了使用银催化的环异构化 - 炔基 N-亚苄基甘氨酸酯的偶极环加成合成与层状生物碱相关的吡咯并异喹啉。机理研究表明，Ag(I) 催化的环异构化为偶氮甲碱叶立德是形成角形吡咯并异喹啉的关键步骤。
• Transformation of Reactive Isochromenylium Intermediates to Stable Salts and Their Cascade Reactions with Olefins
  作者：Zhi-Long Hu、Wen-Jian Qian、Sheng Wang、Shaozhong Wang、Zhu-Jun Yao

  DOI：10.1021/ol9019524

  日期：2009.10.15

  reactive isochromenylium intermediates to the corresponding storable and stable reagents has been achieved, and a number of isochromenylium tetrafluoroborates (ICTBs, 1) have been conveniently prepared and characterized. Direct metal-free treatment of isochromenylium tetrafluoroborate 1a with olefins afforded a variety of polycyclic frameworks 4 via mild cascade reactions. Starting from the prefunctionalized

  已经实现了反应性异戊二烯中间体向相应的可储存和稳定试剂的转化，并且已经方便地制备和表征了许多异丁烯四氟硼酸酯（ICTBs，1）。用轻度的级联反应直接用烯烃对四氟硼酸异铬烯鎓1a进行无金属直接处理，得到了多种多环骨架4。从预官能化的邻炔基苯甲醛开始，还开发了一种一锅无金属的分子内级联环化成2,3-二氢菲咯啉-4（1 H）-一衍生物的方法。