(2E)-2-(Acetoxymethyl)-3-phenylprop-2-enenitrile | 177838-08-3

• 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: (2E)-2-(Acetoxymethyl)-3-phenylprop-2-enenitrile
• 英文别名: (2Z)-2-acetoxymethyl-3-phenyl prop-2-enenitrile；(E)-2-cyano-3-phenylallyl acetate；[(E)-2-cyano-3-phenylprop-2-enyl] acetate
• CAS: 177838-08-3
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: XOUJBRJTVHIJJM-KPKJPENVSA-N

物化性质

• 沸点：
  369.3±37.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 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：

  N-烯丙基对甲苯磺酰胺 、 (2E)-2-(Acetoxymethyl)-3-phenylprop-2-enenitrile 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以60%的产率得到N-[(Z)-2-cyano-3-phenylprop-2-enyl]-4-methyl-N-prop-2-enylbenzenesulfonamide
  参考文献：
  名称：

  Ring-closing metathesis toward the synthesis of 2,5-dihydrofuran and 2,5-dihydropyrrole skeletons from Baylis–Hillman adducts

  摘要：

  We have developed an efficient method for the synthesis of 2,5-dihydrofuran and 15-dihydropyrrole skeletons from the simply modified Baylis-Hillman adducts via RCM reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.047
• 作为产物：
  描述：

  3-acetoxy-2-methylene-3-phenylpropionitrile 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(2E)-2-(Acetoxymethyl)-3-phenylprop-2-enenitrile
  参考文献：
  名称：

  TMSOTf 催化的 Baylis 乙酸酯的立体选择性异构化 - Hillman 加合物

  摘要：

  Baylis-Hillman 加合物的乙酸酯的 TMSOTf 催化异构化，即 3-乙酰氧基-3-芳基-2-亚甲基丙酸甲酯和 3-乙酰氧基-3-芳基-2-亚甲基丙腈提供甲基 (2E)-2-(乙酰氧基甲基)-分别描述了 3-arylprop-2-enoates 和 (2E)-2-(acetoxymethyl)-3-arylprop-2-enenitros。

  DOI：

  10.1055/s-2000-6372

文献信息

• Palladium-catalyzed arylation of methyl 2-(acetoxymethyl)acrylate: a convenient synthesis of rearranged Morita–Baylis–Hillman acetates
  作者：Ko Hoon Kim、Jin Woo Lim、Hyun Ju Lee、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2012.11.026

  日期：2013.1

  Palladium-catalyzed arylation of methyl 2-(acetoxymethyl)acrylate with aryl iodides afforded the primary acetates of Morita–Baylis–Hillman adducts in good yields with high stereoselectivity under mild conditions (50 °C).

  2-（乙酰氧基甲基）丙烯酸甲酯与芳基碘化物的钯催化芳基化反应可在温和的条件下（50°C）以良好的产率和高的立体选择性提供森田-贝利斯-希尔曼加合物的初级乙酸酯。
• 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。
• Bismuth triflate-catalyzed rearrangement of acetates of the Baylis–Hillman adducts into (E)-trisubstituted alkenes
  作者：Thierry Ollevier、Topwe M. Mwene-Mbeja

  DOI：10.1016/j.tet.2008.03.053

  日期：2008.5

  In the presence of a catalytic amount of bismuth triflate, methyl 3-acetoxy-3-aryl-2-methyl-enepropanoates and 3-acetoxy-3-aryl-2-methylenepropanitriles were smoothly converted into methyl (2E)-2-(acetoxymethyl)-3-arylprop-2-enoates and (2E)-2-(acetoxymethyl)-3-arylprop-2-enenitriles, respectively. A remarkable reversal in stereochemical directions from ester to nitrile was observed. 3-Aryl-3-hydroxy-2-methylenepropanoates and 3-aryl-3-hydroxy-2-methylenepropanitriles could be easily obtained as Baylis-Hillman adducts from methyl acrylate and acrylonitrile, respectively. The overall process is an efficient isomerization of the Baylis-Hillman adducts to the corresponding cinnamyl derivatives. The isomerization reaction proceeded rapidly and afforded smoothly the cinnamyl acetates in moderate to very good yields using catalytic amounts of Bi(OTf)(3)center dot 4H(2)O (10 mol%). (c) 2008 Elsevier Ltd. All rights reserved.