Acetic acid 2-cyano-1-(2,4-dichloro-phenyl)-allyl ester | 367487-91-0

• 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: Acetic acid 2-cyano-1-(2,4-dichloro-phenyl)-allyl ester
• 英文别名: [2-Cyano-1-(2,4-dichlorophenyl)prop-2-enyl] acetate
• CAS: 367487-91-0
• 化学式: C₁₂H₉Cl₂NO₂
• 分子量: 270.115
• InChiKey: IDVCTLUGGIGJBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-cyano-1-(2,4-dichloro-phenyl)-allyl ester 在 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 生成 5-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  碘介导通过烯丙基腙中间体从 MBH 乙酸酯一锅法合成 1,4,5-取代吡唑

  摘要：

  描述了通过 Morita-Baylis-Hillman 乙酸酯和肼之间以烯丙基腙为中介的碘介导反应，一锅法区域选择性合成 1,4,5-吡唑。

  DOI：

  10.1002/ejoc.202300355
• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 吡啶 、 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid 2-cyano-1-(2,4-dichloro-phenyl)-allyl ester
  参考文献：
  名称：

  碘介导通过烯丙基腙中间体从 MBH 乙酸酯一锅法合成 1,4,5-取代吡唑

  摘要：

  描述了通过 Morita-Baylis-Hillman 乙酸酯和肼之间以烯丙基腙为中介的碘介导反应，一锅法区域选择性合成 1,4,5-吡唑。

  DOI：

  10.1002/ejoc.202300355

文献信息

• Expeditious synthesis of 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrimidin-2-ones and 3,4,6,7,8,9-hexahydro-pyrimido[1,2-a]pyrimidin-2-ones
  作者：Richa Pathak、Sanjay Batra

  DOI：10.1016/j.tet.2007.06.115

  日期：2007.9

  convenient synthesis of new 5,6,7,8-tetrahydro-imidazo[1,2-a]pyrimidin-2-ones and 3,4,6,7,8,9-hexahydro-pyrimido[1,2-a]pyrimidin-2-ones from the Baylis–Hillman adducts of acrylonitrile and their derivatives is described. A common strategy employed to achieve the syntheses of title compounds involved generation of diamines from different Baylis–Hillman derivatives followed by treatment with cyanogen bromide

  新5,6,7,8-四氢-咪唑并[1,2的方便合成一个]嘧啶-2-酮和-3,4,6,7,8,9-六氢-嘧啶并[1,2一描述了来自丙烯腈的Baylis-Hillman加合物的] pyrimidin-2-ones及其衍生物。用于合成标题化合物的常用策略涉及从不同的Baylis-Hillman衍生物生成二胺，然后在回流温度下用溴化氰处理以引发双分子内环化。
• Montmorillonite K10 Clay-Microwave Assisted Isomerisation of Acetates of the Baylis-Hillman Adducts: A Facile Method of Stereoselective Synthesis of (E)-Trisubstituted Alkenes
  作者：Ponnusamy Shanmugam、Paramasivan Raja Singh

  DOI：10.1055/s-2001-16040

  日期：——

  Montmorillonite K10-microwave assisted stereoselective isomerisation of acetates of the Baylis-Hillman adducts furnished (E)-trisubstituted alkenes in high yields. A comparative study of this reaction with Mont-K10, ion-exchanged clay (Fe3+-Mont-K10) and acid treated regional natural Kaolinite clay and the efficiency of these clays in this reaction is described.

  蒙特莫里隆石K10-微波辅助立体选择性异构化贝利斯-希尔曼加成物的醋酸酯，生成高产率的(E)-三取代烯烃。文中描述了该反应与蒙特-K10、离子交换粘土（Fe3+-蒙特-K10）和酸处理的地方天然高岭土的比较研究，以及这些粘土在该反应中的效率。
• Studies on montmorillonite K10-microwave assisted isomerisation of Baylis–Hillman adduct. Synthesis of E-trisubstituted alkenes and synthetic application to lignan core structures by vinyl radical cyclization
  作者：Ponnusamy Shanmugam、Paramasivan Rajasingh

  DOI：10.1016/j.tet.2004.07.067

  日期：2004.10

  The isomerisation of acetates from the Baylis–Hillman adducts with Mont.K10 clay-microwave combination furnished E-trisubstituted alkenes in high yield. The simple Baylis–Hillman adducts with trimethyl orthoformate and unsaturated alcohols under clay catalytic condition gave densely functionalised-isomerized products under solvent free condition. Application of the propargyl derivatives thus obtained

  来自Baylis-Hillman加合物的乙酸盐与Mont.K10粘土-微波混合物的异构化反应可提供高收率的E-三取代烯烃。在黏土催化条件下，简单的Baylis-Hillman与原甲酸三甲酯和不饱和醇的加合物可在无溶剂条件下得到稠密的官能化异构化产物。从Baylis-Hillman加合物与炔丙醇的异构化反应中获得的炔丙基衍生物的应用已在三氢化正丁基锡氢化物介导的乙烯基自由基环化反应合成木脂素核心结构中得到证明。
• A Facile Construction of 6-(Arylmethyl)imidazo[1,2-<i>a</i>]pyrimidin-7-ylamines from Allylamines Derived from Baylis-Hillman Adducts
  作者：Somnath Nag、Amita Mishra、Sanjay Batra

  DOI：10.1002/ejoc.200800448

  日期：2008.9

  A facile and convenient synthesis of substituted imidazo[1,2-a]pyrimidin-7-ylamines from the allylamine derivatives afforded by the Baylis–Hillman acetates of substituted benzaldehydes and heterocyclic aldehydes by treatment with cyanamide is described. Interestingly, the allylamines afforded by heterocyclic aldehydes, which undergo fast Baylis–Hillman reaction, were discovered to undergo a one-pot

  描述了一种由取代苯甲醛和杂环醛的 Baylis-Hillman 醋酸酯通过用氰胺处理得到的烯丙胺衍生物，简单方便地合成取代的咪唑并 [1,2-a] 嘧啶-7-基胺。有趣的是，杂环醛提供的烯丙胺经过快速 Baylis-Hillman 反应，被发现进行一锅反应，而由所有其他醛衍生的烯丙胺通过两步程序反应。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Trifluoroacetic acid: a more effective and efficient reagent for the synthesis of 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones and 3-arylmethyl-2-amino-quinolines from Baylis–Hillman derivatives via Claisen rearrangement
  作者：Richa Pathak、Sudharshan Madapa、Sanjay Batra

  DOI：10.1016/j.tet.2006.10.053

  日期：2007.1

  Trifluoroacetic acid has been discovered to be a highly effective and efficient reagent for the tandem Claisen rearrangement and cyclization reaction to yield 3-arylmethylene-3,4-dihydro-1H-quinolin-2-ones from compounds obtained from the SN2 reaction between anilines and acetyl derivatives of Baylis–Hillman adducts of acrylates in the presence of DABCO. In contrast, similar compounds obtained from

  已经发现三氟乙酸是用于串联克莱森重排和环化反应以从由S N 2反应获得的化合物产生3-芳基亚甲基-3,4-二氢-1 H-喹啉-2-酮的高效和高效试剂。DABCO存在下苯胺与丙烯酸Bayis-Hillman加合物的乙酰基衍生物之间的关系。相反，在三氟乙酸处理下，从Baylis-Hillman丙烯腈加成物的乙酰基衍生物获得的类似化合物通过串联Claisen重排，环化和异构化直接提供3-芳基甲基-2-氨基-喹啉。