3-氯-3-(4-甲氧基苯基)丙烯醛 | 14063-79-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 中文名称: 3-氯-3-(4-甲氧基苯基)丙烯醛
• 中文别名: (2Z)-3-氯-3-(4-甲氧苯基)丙-2-烯醛
• 英文名称: (Z)-3-chloro-3-(4-methoxyphenyl)acrylaldehyde
• 英文别名: beta-Chloro-p-methoxycinnamaldehyde；(Z)-3-chloro-3-(4-methoxyphenyl)prop-2-enal
• CAS: 14063-79-7
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: ZDHOBXVUKIFNBV-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：

  3-氯-3-(4-甲氧基苯基)丙烯醛 在 sodium sulfide 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.17h， 生成 4-(5-(4-Methoxyphenyl)thiophen-2-yl)benzenamine
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationship of novel thiophene derivatives for β-amyloid plaque imaging

  摘要：

  Novel 2,5-diphenylthiophene derivatives were synthesized and structure activity relationship with regard to A beta plaque binding was studied. Binding affinities of these compounds were found to range from 3.9 to >1000 nM, depending on the substitution patterns on the phenyl ring. The fluoroethyl-substituted thiophene derivatives showed excellent binding affinities. These compounds may be useful for the development of novel PET tracers for the imaging of beta-amyloid plaques in the brain of patients with Alzheimer's disease. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.055
• 作为产物：
  描述：

  3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one 在 三氯氧磷 、 水 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 26.0h， 以98%的产率得到3-氯-3-(4-甲氧基苯基)丙烯醛
  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

• Base-Promoted Intermolecular Cyclization of Substituted 3-Aryl(Heteroaryl)-3-chloroacrylaldehydes and Tetrahydroisoquinolines: An Approach to Access Pyrrolo[2,1-<i>a</i>]isoquinolines
  作者：Ziqi Yang、Ning Lu、Zhonglin Wei、Jungang Cao、Dapeng Liang、Haifeng Duan、Yingjie Lin

  DOI：10.1021/acs.joc.6b01781

  日期：2016.12.2

  We have developed a new base-promoted intermolecular cascade cyclization reaction of substituted 3-aryl(heteroaryl)-3-chloroacrylaldehydes and tetrahydroisoquinolines in one pot. The reaction provides a facile and practical synthesis of pyrrolo[2,1-a]isoquinolines. A number of pyrrolo[2,1-a]isoquinolines were synthesized in moderate to high yields (up to 97%).

  我们已经开发了一种新的碱促进的在一锅中取代的3-芳基（杂芳基）-3-氯丙烯醛和四氢异喹啉的分子间级联环化反应。该反应提供了吡咯并[2，1- a ]异喹啉的简便实用的合成方法。合成了许多吡咯并[2,1- a ]异喹啉，中度至高产率（高达97％）。
• A Useful One-Pot Procedure for Obtaining 2-Aryl-5-nitrothiophenes from Bromonitromethane and 3-Aryl-3-chloro-propenals
  作者：Gilbert Kirsch、Juan Rodríguez-Domínguez、David Thomae、Pierre Seck

  DOI：10.1055/s-2007-1000881

  日期：2008.1

  A one-pot procedure was developed to prepare new 2-aryl-5-nitrothiophenes efficiently from bromonitromethane and 3-chloro-3-aryl-propenals. Nitrothiophenes were synthesized in good yields with a simple and easy workup procedure.

  成功开发了一种一步法，以溴硝基甲烷和3-氯-3-芳基丙烯醛为原料高效合成新型2-芳基-5-硝基噻吩。该方法合成硝基噻吩产率高，操作简便，后处理步骤简单。
• Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents
  作者：Pravin S. Bhale、Hemant V. Chavan、Sakharam B. Dongare、Sadanand N. Shringare、Yoginath B. Mule、Samadhan S. Nagane、Babasaheb P. Bandgar

  DOI：10.1016/j.bmcl.2017.02.052

  日期：2017.4

  they possess high anti-tumor activities. Among them, compound 5e and 5a demonstrated excellent activity against breast carcinoma (GI50 <0.1 and 4μM respectively) as good as adriamycin (GI50 <0.1μM). The compounds were also screened against the normal Vero monkey cell line, which showed moderate selectivity against inhibition of cancer cells. The effect of extended conjugation on activity authenticated

  在本研究中，通过使3-氰基乙酰吲哚2与3-氯-3-苯基-丙烯醛4反应，可以合成一系列扩展的共轭δ-氯-α-氰基取代的吲哚基查耳酮（5a-p）。哌啶。新合成化合物的结构解释基于化学和光谱学证据。对合成化合物体外针对MCF-7（乳腺癌）细胞系的抗肿瘤评价表明，它们具有很高的抗肿瘤活性。其中，化合物5e和5a表现出优异的抗乳腺癌活性（分别为GI50 <0.1和4μM）和阿霉素（GI50 <0.1μM）。还针对正常的Vero猴细胞系筛选了该化合物，后者对癌细胞的抑制作用表现出中等的选择性。通过将化合物5a，5i和5m的活性谱与其简单类似物进行比较，证实了延长的共轭对活性的影响。在合成的化合物中，除了具有显着的抗氧化潜力外，还发现5i和5l是活性抗炎药。这些结果表明这些化合物可能用于设计和开发新型抗乳腺癌药物。
• Ugi Reaction Followed by Intramolecular Diels-Alder Reaction and Elimination of HCl: One-Pot Approach to Arene-Fused Isoindolinones
  作者：Jianjun Huang、Xiaochen Du、Kristof Van Hecke、Erik V. Van der Eycken、Olga P. Pereshivko、Vsevolod A. Peshkov

  DOI：10.1002/ejoc.201700747

  日期：2017.8.17

  A one-pot procedure involving a four-component Ugi reaction followed by an intramolecular Diels–Alder reaction/HCl elimination cascade has been developed to provide rapid access to the isoindolinone framework in a diversity-oriented fashion. The scope of the process has been investigated with respect to all four components, and a comparison between the one-pot and sequential approaches is given. The

  已经开发了一种涉及四组分 Ugi 反应，然后是分子内 Diels-Alder 反应/HCl 消除级联反应的一锅法，以提供以多样性为导向的异吲哚酮框架的快速访问。已经针对所有四个组件研究了该过程的范围，并给出了一锅法和顺序方法之间的比较。已经探索了通过 Suzuki 耦合进行后期一锅功能化的可能性。
• Stereoselective One-Pot Sequential Dehydrochlorination/<i>trans</i> -Hydrofluorination Reaction of β-Chloro-α,β-unsaturated Aldehydes or Ketones: Facile Access to (<i>Z</i> )-β-Fluoro-β-arylenals/β-Fluoro-β-arylenones
  作者：Jingli Zhang、Liran Liu、Junxin Duan、Lianghu Gu、Bifeng Chen、Taolei Sun、Yuefa Gong

  DOI：10.1002/adsc.201700981

  日期：2017.12.19

  high potential as a fluorinated synthon in organic synthesis. However, control of the Z/E stereoselectivity of multi‐substituted monofluoroalkene products in one‐pot reactions still remains a challenge. An unprecedented one‐pot approach for the highly regio‐ and stereoselective preparation of functionalized (Z)‐β‐monofluoro tri‐substituted alkenes from readily available β‐chloro‐α,β‐unsaturated aldehydes

  一氟烯烃亚结构作为有机合成中的氟化合成子显示出很高的潜力。然而，在一锅反应中控制多取代一氟烯烃产物的Z / E立体选择性仍然是一个挑战。对于从容易获得的β-氯代-α，β-不饱和醛或酮进行高度区域和立体选择性制备官能化（Z）-β-单氟三取代烯烃的空前单锅方法已被探索。机理研究表明，该反应是通过将底物脱氯化氢而生成炔基醛/酮，然后将其反式引发的。-氟化氢。值得一提的是，具有适当碱性和亲核性的氟化剂在促进（Z）-β-氟-β-芳基三取代单氟烯烃的形成中起着关键作用。