5-(but-3-en-1-yloxy)benzo[d][1,3]dioxole | 195250-18-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(but-3-en-1-yloxy)benzo[d][1,3]dioxole
• 英文别名: 5-But-3-enoxy-1,3-benzodioxole
• CAS: 195250-18-1
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: LABNXTIQHDVUDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(but-3-en-1-yloxy)benzo[d][1,3]dioxole 在 双(乙腈)氯化钯(II) sodium carbonate 、 对苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以59%的产率得到4-methyl-6,7-methylenedioxy-2H-chromene
  参考文献：
  名称：

  通过PdII催化的氧化环化反应，可轻松构建苯并呋喃和亚甲基环系统。

  摘要：

  [反应：请参见文字]。我们在本文中报道了一锅法的发展，该方法用于将烯丙基芳基醚转化为2-甲基苯并呋喃（通过顺序的克莱森重排和氧化环化）和用于将芳基高烯丙基醚转化为苯甲基（通过直接氧化环化）。这两种反应都有可能通过常见的Pd催化途径进行，涉及烯烃活化，亲核攻击和β-氢化物消除。

  DOI：

  10.1021/ol051264z
• 作为产物：
  描述：

  芝麻酚 、 丁-3-烯-1-醇,4-甲基苯磺酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以50%的产率得到5-(but-3-en-1-yloxy)benzo[d][1,3]dioxole
  参考文献：
  名称：

  Intramolecular Photochemical Reactions of Bichromophoric 3-(Alkenyloxy)phenols and 1-(Alkenyloxy)-3-(alkyloxy)benzene Derivatives. Acid-Catalyzed Transformations of the Primary Cycloadducts

  摘要：

  Irradiation of 3-(alkenyloxy)phenols and 1-(alkenyloxy)-3-(alkyloxy)benzene derivatives, at lambda = 254 nm in acidic media, yields benzocyclobutenes, 3-alkylphenols, 3-alkylanisols, and 4-alkyl-1,2-dialkyloxybenzenes depending on the substitution pattern of the aromatic ring and the olefinic side chain. The final products are derived from an intramolecular [2 + 2] photocycloaddition and acidic rearrangements from a common intermediate.

  DOI：

  10.1021/jo970554t

文献信息

• Palladium-Catalyzed Carbonylative Cyclization of Aryl Alkenes/Alkenols: A New Reaction Mode for the Synthesis of Electron-Rich Chromanes
  作者：Shuang Li、Fuzhuo Li、Jianxian Gong、Zhen Yang

  DOI：10.1021/acs.orglett.5b00214

  日期：2015.3.6

  The Pd(II)-catalyzed intramolecular carbonylative cyclization reaction of aryl alkenes and aryl alkenols is reported for the synthesis of structurally diverse chromanes. PdCl2(CH3CN)2 was used as the catalyst and CuCl2 as the oxidant under the balloon pressure of CO. The reaction is conducted under mild conditions, and chromane-type esters and lactones can be generated in a highly regio- and stereoselective

  据报道，Pd（II）催化的芳基烯烃和芳基烯醇的分子内羰基化环化反应可合成结构多样的苯并二氢吡喃。在CO的球囊压力下，将PdCl 2（CH 3 CN）2用作催化剂，将CuCl 2用作氧化剂。反应在温和的条件下进行，并且可以在高区域和高纯度下生成苯并二氢吡喃型酯和内酯。立体选择性的方式。
• Copper‐Catalyzed 1,2‐Trifluoromethylation Carbonylation of Unactivated Alkenes: Efficient Access to β‐Trifluoromethylated Aliphatic Carboxylic Acid Derivatives
  作者：Fu‐Peng Wu、Yang Yuan、Xiao‐Feng Wu

  DOI：10.1002/anie.202112609

  日期：2021.12

  A novel procedure on carbonylative trifluoromethylation of unactivated alkenes has been developed. Catalyzed by a copper catalyst, carbonylative difunctionalization of alkenes with Togni-CF3 and nitrogen (or oxygen) nucleophiles occurred successfully. A variety of valuable β-trifluoromethyl amides, esters and acids were obtained in good yields under mild conditions. Ethylene gas can also be successfully

  已开发出未活化烯烃的羰基化三氟甲基化的新方法。在铜催化剂的催化下，烯烃与 Togni-CF 3和氮（或氧）亲核试剂的羰基化双官能化成功发生。在温和的条件下以良好的收率获得了多种有价值的β-三氟甲基酰胺、酯和酸。乙烯气体也可以成功应用。
• Copper-Catalyzed Synthesis of Stereodefined Cyclopropyl Bis(boronates) from Alkenes with CO as the C1 Source
  作者：Fu-Peng Wu、Xiaoling Luo、Udo Radius、Todd B. Marder、Xiao-Feng Wu

  DOI：10.1021/jacs.0c06800

  日期：2020.8.19

  A novel copper-catalyzed stereodefined procedure for the selective synthesis of cyclopropyl bis(boronates) from terminal alkenes has been developed. Various aliphatic alkenes were transformed into the desired bis(boronate ester)-substituted cyclopropanes in moderate to good yields. Synthetic transformations of the resulting cyclopropyl bis(boronates) demonstrate their utility. A possible reaction mechanism

  已经开发了一种新的铜催化立体定义方法，用于从末端烯烃选择性合成环丙基双（硼酸酯）。各种脂肪族烯烃以中等至良好的产率转化为所需的双（硼酸酯）取代的环丙烷。所得环丙基双（硼酸酯）的合成转化证明了它们的实用性。提出了一种可能的反应机理。
• Electrochemical Activation of Nitromethane to Construct Isoxazoline Aldoximes
  作者：Shuaiyu Ji、Lixing Zhao、Bingyang Miao、Meng Xue、Tao Pan、Zhichao Shao、Xin Zhou、Aiping Fu、Yuexia Zhang

  DOI：10.1002/anie.202304434

  日期：2023.8.7

  An unprecedented approach to isoxazoline aldoximes via the reactions of nitromethane and olefins is achieved. Nitromethane is electrochemically activated to serve as both the heterocyclic skeleton and oxime sources for the construction of isoxazoline aldoximes.

  通过硝基甲烷和烯烃的反应实现了制备异恶唑啉醛肟的前所未有的方法。硝基甲烷被电化学活化，作为构建异恶唑啉醛肟的杂环骨架和肟源。
• Facile Construction of the Benzofuran and Chromene Ring Systems via Pd^II-Catalyzed Oxidative Cyclization
  作者：So Won Youn、Jeong Im Eom

  DOI：10.1021/ol051264z

  日期：2005.7.1

  text]. We herein report the development of one-pot procedures for the conversion of allyl aryl ethers to 2-methylbenzofurans (via sequential Claisen rearrangement and oxidative cyclization) and for the conversion of aryl homoallyl ethers to chromenes (via direct oxidative cyclization). It is likely that both reactions proceed via a common Pd-catalyzed pathway involving olefin activation, nucleophilic

  [反应：请参见文字]。我们在本文中报道了一锅法的发展，该方法用于将烯丙基芳基醚转化为2-甲基苯并呋喃（通过顺序的克莱森重排和氧化环化）和用于将芳基高烯丙基醚转化为苯甲基（通过直接氧化环化）。这两种反应都有可能通过常见的Pd催化途径进行，涉及烯烃活化，亲核攻击和β-氢化物消除。