3-Buten-2-one, 3-[(acetyloxy)(4-methylphenyl)methyl]- | 367487-95-4

• 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: 3-Buten-2-one, 3-[(acetyloxy)(4-methylphenyl)methyl]-
• 英文别名: [2-methylidene-1-(4-methylphenyl)-3-oxobutyl] acetate
• CAS: 367487-95-4
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: UQNSFQOHOKDDIR-UHFFFAOYSA-N

物化性质

• 沸点：
  357.6±42.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Buten-2-one, 3-[(acetyloxy)(4-methylphenyl)methyl]- 在 potassium carbonate 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 7.0h， 生成 1-[(5Z)-4-methyl-5-[(4-methylphenyl)methylidene]-1-(4-methylphenyl)sulfonyl-2,6-dihydropyridin-3-yl]ethanone
  参考文献：
  名称：

  Regioselective construction of polysubstituted pyridine ring from Baylis–Hillman adducts via sequential introduction of tosylamide, Michael reaction, aldol condensation, and elimination of TsH

  摘要：

  Facile synthetic method of polysubstituted pyridine derivatives was developed starting from the Baylis-Hillman adducts. The reaction involved sequential introduction of tosylamide, Michael addition, aldol condensation, elimination of p-toluenesulfinic acid, and isomerization process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.034

文献信息

• Chiral Phosphine-Catalyzed Enantioselective Construction of γ-Butenolides Through Substitution of Morita−Baylis−Hillman Acetates with 2-Trimethylsilyloxy Furan
  作者：Ying-Qing Jiang、Yong-Ling Shi、Min Shi

  DOI：10.1021/ja802422d

  日期：2008.6.1

  Chiral multifunctional phosphine (R)-N-(2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-yl)methanesulfonamide L2 or (R)-N-(2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-yl)acetamide L3 is an efficient catalyst in the allylic substitutions of MBH acetates 1 with 2-trimethylsilyloxy furan 2 to provide gamma-butenolides 3 in good to excellent yields and enantiomeric excesses in the presence of water.

  手性多功能膦 (R)-N-(2'-二苯基膦酰基-[1,1']联萘基-2-基)甲磺酰胺 L2 或 (R)-N-(2'-二苯基膦酰基-[1,1']联萘基- 2-基）乙酰胺 L3 是 MBH 乙酸酯 1 与 2-三甲基甲硅烷氧基呋喃 2 烯丙基取代的有效催化剂，以在水存在下以良好至极好的产率和对映体过量提供 γ-丁烯内酯 3。
• 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。
• Chiral Bifunctional Thiourea-Phosphane Organocatalysts in Asymmetric Allylic Amination of Morita-Baylis-Hillman Acetates
  作者：Hong-Ping Deng、Yin Wei、Min Shi

  DOI：10.1002/ejoc.201001660

  日期：2011.4

  A series of new chiral bifunctional thiourea-phosphane catalysts was synthesized and successfully applied in the catalytic, asymmetric allylic amination of Morita-Baylis-Hillman (MBH) acetates derived from the methyl vinyl ketone (MVK) or ethyl vinyl ketone (EVK) system, with phthalimide, affording the amination products in up to over 99 % yield and 90 % ee for a wide range of substrates derived from

  合成了一系列新型手性双官能硫脲-磷烷催化剂，并成功应用于甲基乙烯基酮（MVK）或乙基乙烯基酮（EVK）体系衍生的 Morita-Baylis-Hillman（MBH）乙酸酯的催化不对称烯丙基胺化反应，使用邻苯二甲酰亚胺，对于衍生自不同芳香醛的各种底物，胺化产物的产率高达 99% 以上，ee 高达 90%。
• FeCl₃and Yb(OTf)₃Mediated Conversion of Acetates of the Baylis–Hillman Adducts into (Z) and (E) Trisubstituted Alkenes
  作者：Palakodety Radha Krishna、V. Kannan、G. V. M. Sharma

  DOI：10.1081/scc-120027238

  日期：2004.12.31

  Abstract Anhydrous FeCl3 and Yb(OTf)3 are utilised as new reagents for the stereoselective isomerisation of acetates of the Baylis–Hillman adducts to both (Z) and (E) trisubstituted alkenes respectively.

  摘要 无水 FeCl3 和 Yb(OTf)3 被用作新试剂，分别将 Baylis-Hillman 加合物的乙酸酯立体选择性异构化为 (Z) 和 (E) 三取代烯烃。