methyl 4-(4-methoxyphenyl)but-2-ynoate | 445234-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-(4-methoxyphenyl)but-2-ynoate
• 英文别名: 2-Butynoic acid, 4-(4-methoxyphenyl)-, methyl ester
• CAS: 445234-72-0
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: XNDRQCDZTQQKRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 、 methyl 4-(4-methoxyphenyl)but-2-ynoate 在 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 以96%的产率得到methyl (E)-3-[(E)-5-[(2R)-3,3-dimethyloxiran-2-yl]-3-methylpent-2-enoxy]-4-(4-methoxyphenyl)but-2-enoate
  参考文献：
  名称：

  Oxygen-containing analogues of juvenile hormone III

  摘要：

  Juvenile hormone III (JH-III) controls several aspects of insect development, and analogues of JH-III are widely used as insect control agents. Recent reports suggest that these compounds may also perturb the normal development of crustaceans, and perhaps other aquatic species. In an attempt to prepare more highly degradable (and thus less environmentally persistent) mimics of JH-III, we prepared a series of analogues incorporating vinyl ether functionality. The stability of these compounds in water or warm, moist air was evaluated, revealing two distinct decomposition pathways. Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.103
• 作为产物：
  描述：

  4-甲氧基溴苄 、 丙炔酸甲酯 在 copper(l) iodide 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以75%的产率得到methyl 4-(4-methoxyphenyl)but-2-ynoate
  参考文献：
  名称：

  Operationally Simple Copper-Promoted Coupling of Terminal Alkynes with Benzyl Halides

  摘要：

  Benzyl chlorides and bromides are shown to undergo copper-promoted coupling with a variety of terminal alkynes including, for the first time, electron-poor acetylenes such as methyl propiolate. The reaction permits easy access to a wide range of (functionalized) benzyl-substituted propiolates (as well as several related alkynes) from commercially available benzyl halides. These products should in turn function as useful building blocks for the synthesis of previously inaccessible (functionalized) benzyl-substituted heterocycles.

  DOI：

  10.1021/jo900444x

文献信息

• Enantioselective Intermolecular Radical C–H Amination
  作者：Li-Mei Jin、Pan Xu、Jingjing Xie、X. Peter Zhang

  DOI：10.1021/jacs.0c10415

  日期：2020.12.9

  noncovalent attractive interactions through fine-tuning of the remote substituents of the D2-symmetric chiral amidoporphyrin ligand. This noncovalent interaction strategy presents a solution that may be generally applicable in controlling reactivity and enantioselectivity in intermolecular radical reactions. The Co(II)-catalyzed intermolecular C-H amination, which operates under mild conditions with the C-H

  自由基反应在有机合成中具有许多固有优势，可能会影响有机分子构建的规划和实践。然而，自由基过程中对映选择性的控制仍然是长期存在的挑战之一。虽然最近在分子内自由基反应方面取得了重大进展，但分子间自由基反应中的不对称诱导的控制仍然提出了具有挑战性的问题。我们在此报告了一种催化方法，该方法通过基于 Co(II) 的金属自由基催化 (MRC) 控制对映选择性以及羧酸酯与有机叠氮化物的分子间自由基 CH 胺化的反应性。成功的关键在于通过微调 D2 对称手性酰胺卟啉配体的远程取代基来最大化非共价吸引力相互作用的催化剂开发。这种非共价相互作用策略提供了一种解决方案，可普遍适用于控制分子间自由基反应的反应性和对映选择性。Co(II) 催化的分子间 CH 胺化反应在温和条件下以 CH 底物为限制试剂，表现出广泛的底物范围和高化学选择性，为获得具有高对映选择性的有价值的手性氨基酸衍生物提供了有效途径。系统的机理研究揭示了基于
• Sulfoximidations of Benzylic C−H bonds by Photocatalysis
  作者：Han Wang、Duo Zhang、Carsten Bolm

  DOI：10.1002/anie.201801660

  日期：2018.5.14

  An efficient photocatalytic functionalization of compounds with benzylic C−H bonds by sulfoximidation in visible light is described. The mild reaction conditions allow the use of a broad array of substrates, including diarylmethane, alkyl arenes, arylacetonitrile, 2‐arylacetate, and alkynyl aryl methanes. The sulfoximidation process is highly chemoselective and leads to the corresponding sulfoximines

  描述了在可见光下通过亚磺酰亚胺化对具有苄基CH键的化合物进行的有效光催化功能化。温和的反应条件允许使用多种底物，包括二芳基甲烷，烷基芳烃，芳基乙腈，2-芳基乙酸酯和炔基芳基甲烷。亚磺酰亚胺化过程具有高度的化学选择性，并以通常良好的收率产生了相应的亚磺酰亚胺。机理研究表明，磺酰亚氨基自由基是中间的。
• Catalytic Enantioselective Carbon–Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C–H Bonds
  作者：Daniel T. Ziegler、Gregory C. Fu

  DOI：10.1021/jacs.6b08486

  日期：2016.9.21

  Benzylic alcohols and ethers are common subunits in bioactive molecules, as well as useful intermediates in organic chemistry. In this Communication, we describe a new approach to the enantioselective synthesis of benzylic ethers through the chiral phosphine-catalyzed coupling of two readily available partners, γ-aryl-substituted alkynoates and alcohols, under mild conditions. In this process, the

  苯甲醇和醚是生物活性分子中常见的亚基，也是有机化学中有用的中间体。在这篇通讯中，我们描述了一种通过手性膦催化偶联两个容易获得的伙伴，γ-芳基取代的炔酸酯和醇，在温和条件下对映选择性合成苄醚的新方法。在这个过程中，炔酸伙伴进行内部氧化还原反应。具体而言，苄基位置以良好的对映选择性氧化，炔烃被还原为烯烃。
• An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis
  作者：Keisuke Tonogaki、Miwako Mori

  DOI：10.1016/s0040-4039(02)00215-0

  日期：2002.3

  Synthesis of 1,3-diene from alkyne and ethylene (1 atm) was improved using ruthenium carbene complex 1b having heterocyclic carbene as a ligand. In this reaction, the heteroatom at the propargylic position was not required, although the reaction of alkyne with the first-generation ruthenium carbene complex 1a was affected by the substituent at the propargylic position. Various 1,3-dienes could be synthesized

  使用具有杂环卡宾作为配体的钌卡宾配合物1b，可以改善由炔烃和乙烯（1 atm）合成1,3-二烯的能力。在该反应中，尽管炔烃与第一代钌卡宾配合物1a的反应受到炔丙基位置上的取代基的影响，但在炔丙基位置上不需要杂原子。各种1，3-二烯可以由炔烃和乙烯合成。
• SYNTHESIS OF 1,3-DIENES FROM ALKYNES AND ETHYLENE: ACETIC ACID 2-METHYLENE-3-PHENETHYLBUT-3-ENYL ESTER
  作者：Mori, Miwako、Tonogaki, Keisuke、Kinoshita, Atsushi

  DOI：10.15227/orgsyn.081.0001

  日期：——