(Z)-β-bromo-β-(4-methoxyphenyl)acrolein | 244625-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (Z)-β-bromo-β-(4-methoxyphenyl)acrolein
• 英文别名: (Z)-3-bromo-3-(4-methoxyphenyl)acrylaldehyde；(Z)-3-bromo-3-(4-methoxyphenyl)acrolein；(Z)-3-bromo-3-(4-methoxyphenyl)prop-2-enal
• CAS: 244625-26-1
• 化学式: C₁₀H₉BrO₂
• 分子量: 241.084
• InChiKey: AORLAQOLHIYLPO-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-β-bromo-β-(4-methoxyphenyl)acrolein 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到3,4-二甲氧基苯乙炔
  参考文献：
  名称：

  The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones

  摘要：

  Studies directed at the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones from (Z)-3-aryl-3-haloenoic acids are described The successful strategy relies on the preparation of (Z)-3-aryl-3-haloenoic acids from acetophenones through the corresponding (Z)-3-aryl-3-haloenals and the conversion of the (Z)-3-aryl-3-haloenoic acids to (Z)-5-benzylidene-4-aryl-5H-furan-2-ones The furanones were subsequently treated with primary amines and dehydrated to the corresponding (Z)-5-benzylidene-4-arylpyrrol-2(5H)-one (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.080
• 作为产物：
  描述：

  3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one 在 三溴氧磷 、 水 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到(Z)-β-bromo-β-(4-methoxyphenyl)acrolein
  参考文献：
  名称：

  The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones

  摘要：

  Studies directed at the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones from (Z)-3-aryl-3-haloenoic acids are described The successful strategy relies on the preparation of (Z)-3-aryl-3-haloenoic acids from acetophenones through the corresponding (Z)-3-aryl-3-haloenals and the conversion of the (Z)-3-aryl-3-haloenoic acids to (Z)-5-benzylidene-4-aryl-5H-furan-2-ones The furanones were subsequently treated with primary amines and dehydrated to the corresponding (Z)-5-benzylidene-4-arylpyrrol-2(5H)-one (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.080

文献信息

• 一种呋喃大环化合物制备方法及制备的呋喃大环化合物和应用
  申请人：华南理工大学

  公开号：CN113214283B

  公开（公告）日：2022-09-30

  本发明公开了一种呋喃大环化合物的制备方法及其制备的呋喃大环化合物和应用。本发明的制备方法是以大环炔烯醛化合物为原料在金属催化下发生成环反应。本发明的制备方法操作简单，步骤简便，效率高，原子利用率高达100％。反应原料大环炔烯醛化合物可以由环酮类化合物或烷基醇类化合物经过工艺成熟，效率很高的几步反应得到。本发明的方法得到一种结构全新并且特殊的呋喃大环化合物，其可以作为基元单位合成一系列低聚呋喃化合物，有潜在的光学应用价值。
• Synthesis and stereochemistry of β-aryl-β-haloacroleins: useful intermediates for the preparation of (Z ) and (E )-2-en-4-ynecarbaldehydes and for the synthesis of rubrolides
  作者：Damien Prim、Alexia Fuss、Gilbert Kirsch、Artur M. S. Silva

  DOI：10.1039/a900286c

  日期：——

  The synthesis of α-substituted β-aryl-β-haloacroleins by two different pathways is presented. The determination of their stereochemistry by NOE experiments is reported for the first time. Furthermore, we describe the preparation of 2-en-4-ynecarbaldehydes and access to rubrolide derivatives from β-aryl-β-haloacroleins.

  提出了通过两种不同途径合成α-取代的β-芳基-β-卤代丙烯醛的方法。首次报道了通过NOE实验确定其立体化学。此外，我们描述了2-en-4-炔甲醛的制备方法以及从β-芳基-β-卤代丙烯醛中获得Rubrolide衍生物的方法。
• Functionalized Alkenylzinc Reagents Bearing Carbonyl Groups: Preparation by Direct Metal Insertion and Reaction with Electrophiles
  作者：Christoph Sämann、Matthias A. Schade、Shigeyuki Yamada、Paul Knochel

  DOI：10.1002/anie.201302058

  日期：2013.9.2

  cyclic and acyclic alkenylzinc reagents bearing functional groups such as aldehyde, keto, and ester groups were readily prepared by either direct zinc insertion in the presence of LiCl or by magnesium insertion in the presence of LiCl and ZnCl2. Subsequent functionalization reactions, such as Negishi cross‐couplings, acylations, and allylations, furnished polyfunctional compounds in excellent yields

  带有官能团如醛基，酮基和酯基的高度官能化的环状和无环烯基锌试剂可以通过在LiCl存在下直接锌插入或在LiCl和ZnCl 2存在下通过镁插入而容易地制备。随后的官能化反应（例如Negishi交叉偶联，酰化和烯丙基化）以优异的收率提供了多官能化合物。
• Base-Promoted One-Pot Sequential Phosphite Addition and 5-exo-dig Cyclization of Enynals: A Facile Route to Trisubstituted Furans
  作者：K. Kumara Swamy、Anasuyamma Uravakilli、Ramesh Kotikalapudi

  DOI：10.1055/s-0033-1340865

  日期：——

  using the same substrates leads to a diene product. An easy route for the synthesis of trisubstituted furans has been demonstrated. One-pot sequential phosphite (H-phosphonate) addition to alkynylaldehydes (enynals) promoted by tripotassium phosphate leads to trisubstituted furans (phosphono-furans) via 5-exo-dig cyclization of the phosphono-alkynol intermediates. In contrast, in the presence of silver(I)

  摘要 已经证明了合成三取代呋喃的简便方法。由磷酸三钾促进的向炔基醛（烯醛）中加一锅的连续亚磷酸酯（H-膦酸酯）通过膦酰基-炔醇中间体的5-外-环化作用导致三取代的呋喃（膦酰基-呋喃）。相反，在四氟硼酸银（I）的存在下，使用相同底物的反应产生二烯产物。 已经证明了合成三取代呋喃的简便方法。由磷酸三钾促进的向炔基醛（烯醛）中加一锅的连续亚磷酸酯（H-膦酸酯）通过膦酰基-炔醇中间体的5-外-环化作用导致三取代的呋喃（膦酰基-呋喃）。相反，在四氟硼酸银（I）的存在下，使用相同底物的反应产生二烯产物。
• Synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives from β-halo styrene derivatives and their application in the synthesis of trisubstituted pyridines
  作者：Vijayalakshmi Bandi、Veerababurao Kavala、Che-Hao Hsu、Ashok Konala、Bharath Kumar Villuri、Trimurtulu Kotipalli、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1039/c7ra07128k

  日期：——

  approach for the synthesis of functionalized unsymmetrical 1,3-butadiene-3-yne derivatives is reported starting from β-halo styrene and phenyl acetylene derivatives in the presence of PdCl2 and CuI catalysts. Functional groups such as aldehyde, cyano and ester groups are well tolerated and afford the desired functionalized dienynes. Further, these 1,3-buta-diene-3-yne derivatives are utilized for the

  据报道，在PdCl 2和CuI催化剂存在下，从β-卤代苯乙烯和苯基乙炔衍生物开始合成官能化的不对称1,3-丁二烯-3-炔衍生物的方法。诸如醛基，氰基和酯基的官能团具有良好的耐受性，并提供所需的官能化二烯。此外，这些1，3-丁二烯-3-炔衍生物被用于合成新的三取代的吡啶衍生物。