4-(4-methoxyphenyl)but-3-en-2-yl acetate | 158322-87-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)but-3-en-2-yl acetate
• CAS: 158322-87-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: FSXWBUZBQJPOBF-UHFFFAOYSA-N

物化性质

• 沸点：
  331.3±30.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)but-3-en-2-yl acetate 在 三甲基氯硅烷 、 lithium diisopropyl amide 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以77%的产率得到
  参考文献：
  名称：

  Ireland-Claisen rearrangement of secondary allyl acetate revisited: inevitable C-silylation circumvented by one-pot application of excessive LDA/TMSCl and TBAF

  摘要：

  Yield lowering C-silylation was found to be inevitable in all the six tested examples of stoichiometric LDA/TMSCl promoted Ireland-Claisen rearrangement of secondary allyl acetates. In order to circumvent this problem, a higher yielding protocol was devised after the isolated by-products were found to be excellent substrates for further rearrangement. Thus, excessive LDA/TMSCl was applied to achieve complete 3,3'-sigmatropic shift of the substrates, and the resulting mixtures of normal and alpha-silylated gamma,delta-unsaturated carboxylic acids was then desilylated by one-pot application of TBAF. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.071
• 作为产物：
  描述：

  对甲氧苯乙烯基甲基酮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(4-methoxyphenyl)but-3-en-2-yl acetate
  参考文献：
  名称：

  氢键促进的钯催化：使用手性双（亚砜）膦配体的不对称1,3-二取代烯丙基乙酸酯与吲哚的烯丙基烷基化

  摘要：

  DYKAT努力奋斗：新型的手性BiSO-P配体通过动态动力学不对称转化（DYKAT）有效地实现了前所未有的钯催化的吲哚与外消旋乙酸酯的吲哚不对称烯丙基烷基化反应。在配体的亚磺酰基和吲哚的NH之间形成的氢键在反应中起重要作用。

  DOI：

  10.1002/anie.201209485

文献信息

• Mechanism of Visible Light-Mediated Alkene Aminoarylation with Arylsulfonylacetamides
  作者：Anthony R. Allen、Jia-Fei Poon、Rory C. McAtee、Nicholas B. Watson、Derek A. Pratt、Corey R.J. Stephenson

  DOI：10.1021/acscatal.2c02577

  日期：2022.7.15

  Alkene aminoarylation with arylsulfonylacetamides via a visible light-mediated radical Smiles–Truce rearrangement represents a convenient approach to the privileged arylethylamine pharmacophore traditionally generated by circuitous, multistep sequences. Herein, we report detailed synthetic, spectroscopic, kinetic, and computational studies designed to interrogate the proposed mechanism, including the

  通过可见光介导的自由基 Smiles-Truce 重排，将烯烃与芳基磺酰基乙酰胺进行氨基芳基化，代表了一种传统上通过迂回、多步序列生成的特权芳基乙胺药效团的便捷方法。在此，我们报告了详细的合成、光谱、动力学和计算研究，旨在探讨所提出的机制，包括关键的芳基转移事件。这些数据与限速 1,4-芳基迁移一致，该迁移要么通过涉及自由基 Meisenheimer 类中间体的逐步过程发生，要么以依赖于芳烃电子和烯烃空间的协调方式发生。
• Enantioselective C3‐Allylation of Pyridines via Tandem Borane and Palladium Catalysis
  作者：Jun‐Jie Tian、Rui‐Rui Li、Gui‐Xiu Tian、Xiao‐Chen Wang

  DOI：10.1002/anie.202307697

  日期：2023.8.21

  A one-pot, three-step method for highly enantioselective C3-allylation reactions of pyridines was developed. The method involved borane-catalyzed dearomative pyridine hydroboration, palladium-catalyzed enantioselective allylation of the dearomatized intermediate, and finally oxidation by air. The method was applicable to a broad range of pyridines, N-heteroarenes, and allylic esters.

  开发了一种用于吡啶的高度对映选择性 C3 烯丙基化反应的一锅三步方法。该方法包括硼烷催化的脱芳基吡啶硼氢化反应、钯催化的脱芳基中间体的对映选择性烯丙基化反应，以及最后的空气氧化反应。该方法适用于多种吡啶、N-杂芳烃和烯丙酯。
• Hydrogen-Bond-Promoted Palladium Catalysis: Allylic Alkylation of Indoles with Unsymmetrical 1,3-Disubstituted Allyl Acetates Using Chiral Bis(sulfoxide) Phosphine Ligands
  作者：Le Du、Peng Cao、Junwei Xing、Yazhou Lou、Liyin Jiang、Liangchun Li、Jian Liao

  DOI：10.1002/anie.201209485

  日期：2013.4.8

  A DYKAT die hard: A new class of chiral BiSO‐P ligands were effective for an unprecedented palladium‐catalyzed asymmetric allylic alkylation of indoles with the racemic title acetates through a dynamic kinetic asymmetric transformation (DYKAT). The hydrogen bond formed between the sulfinyl group of the ligand and NH of indole plays an important role in the reaction.

  DYKAT努力奋斗：新型的手性BiSO-P配体通过动态动力学不对称转化（DYKAT）有效地实现了前所未有的钯催化的吲哚与外消旋乙酸酯的吲哚不对称烯丙基烷基化反应。在配体的亚磺酰基和吲哚的NH之间形成的氢键在反应中起重要作用。
• Ireland-Claisen rearrangement of secondary allyl acetate revisited: inevitable C-silylation circumvented by one-pot application of excessive LDA/TMSCl and TBAF
  作者：Di Liu、Xiaoming Yu

  DOI：10.1016/j.tetlet.2012.02.071

  日期：2012.4

  Yield lowering C-silylation was found to be inevitable in all the six tested examples of stoichiometric LDA/TMSCl promoted Ireland-Claisen rearrangement of secondary allyl acetates. In order to circumvent this problem, a higher yielding protocol was devised after the isolated by-products were found to be excellent substrates for further rearrangement. Thus, excessive LDA/TMSCl was applied to achieve complete 3,3'-sigmatropic shift of the substrates, and the resulting mixtures of normal and alpha-silylated gamma,delta-unsaturated carboxylic acids was then desilylated by one-pot application of TBAF. (c) 2012 Elsevier Ltd. All rights reserved.