1-acetoxy-1-(3',4'-methylenedioxyphenyl)but-3-ene | 5420-97-3

• 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: 1-acetoxy-1-(3',4'-methylenedioxyphenyl)but-3-ene
• 英文别名: 1-(1,3-Benzodioxol-5-yl)but-3-enyl acetate
• CAS: 5420-97-3
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: SEPMDINTZXVARF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-acetoxy-1-(3',4'-methylenedioxyphenyl)but-3-ene 在 chromium(VI) oxide 、 palladium dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以73%的产率得到1-(benzo[d][1,3]dioxol-5-yl)-3-oxobutyl acetate
  参考文献：
  名称：

  使用模仿Wacker工艺的PdCl 2 / CrO 3系统由末端烯烃合成甲基酮

  摘要：

  开发了使用模仿Wacker工艺的PdCl 2 / CrO 3系统从末端烯烃高效合成甲基酮的方法。该方法显示出良好的官能团相容性，没有醛副产物，并且操作简单。CrO 3是唯一的氧化剂，可替代传统上在此过程中使用的铜盐和分子氧。该方法具有在有机合成中未来应用的潜力。

  DOI：

  10.1016/j.tet.2014.05.022
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 1-acetoxy-1-(3',4'-methylenedioxyphenyl)but-3-ene
  参考文献：
  名称：

  Chen; Barthel,

  摘要：

  DOI：

文献信息

• Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones
  作者：Dipali A. Chaudhari、Rodney A. Fernandes

  DOI：10.1021/acs.joc.6b00137

  日期：2016.3.4

  the Wacker process for C═O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess–Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.

  可以通过Pd（II）和高价碘试剂Dess-Martin高碘烷的组合来引发Wacker在末端烯烃中形成C═O键的过程的模拟，以生成甲基酮。该操作简单且可扩展的方法提供了马尔可夫尼科夫选择性，具有良好的官能团相容性，且温和且产率高。
• Scandium Triflate Catalyzed Allylation of Acetals and <i>gem</i>-Diacetates: A Facile Synthesis of Homoallyl Ethers and Acetates
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、P. Srihari

  DOI：10.1055/s-2001-13379

  日期：——

  Scandium triflate catalyzes efficiently the allylation reactions of acetals and gem-diacetates with allyltrimethylsilane at ambient temperature to afford the corresponding homoallyl ethers and acetates in high yields. Also it is found to be effective for the direct formation of homoallyl ethers from aldehydes and allylsilane in presence of trimethylorthoformate.

  三氟甲磺酸钪在环境温度下有效催化缩醛和偕二乙酸酯与烯丙基三甲基硅烷的烯丙基化反应，以高收率提供相应的均烯丙基醚和乙酸酯。还发现它对于在原甲酸三甲酯存在下由醛和烯丙基硅烷直接形成均烯丙基醚是有效的。
• Indium(III) Chloride Catalyzed Allylation of<i>gem</i>-Diacetates: A Facile Synthesis of Homoallyl Acetates
  作者：J. S. Yadav、B. V. Subba Reddy、Ch. Madhuri、G. Sabitha

  DOI：10.1246/cl.2001.18

  日期：2001.1

  Indium(III) chloride is found to catalyze efficiently the allylation of gem-diacetates with allyltrimethylsilane at room temperature to afford the corresponding homoallylic acetates in high yields with good regioselectivity.

  研究发现，氯化铟（III）可在室温下高效催化烯丙基三甲基硅烷与宝石二乙酸酯的烯丙基化反应，从而以高产率和良好的区域选择性制备出相应的均烯丙基乙酸酯。
• Oxonia-Cope Rearrangement and Side-Chain Exchange in the Prins Cyclization
  作者：Stuart R. Crosby、John R. Harding、Clare D. King、Gregory D. Parker、Christine L. Willis

  DOI：10.1021/ol0102850

  日期：2002.2.1

  [GRAPHICS]Evidence is presented here for the mechanism of the Prins cyclization of benzylic homoallylic alcohols, which shows that the outcome of the reaction is dependent upon the substituents on the aromatic ring. The presence of an electron-rich aromatic ring favors an oxonia-Cope rearrangement yielding a symmetrical tetrahydropyran as the major product formed via a side-chain exchange process. In contrast, with electron-deficient aromatic rings the expected 2,4,6-trisubstituted tetrahydropyran is formed.
• Prins Cyclizations:  Labeling Studies and Application to Natural Product Synthesis
  作者：Stuart R. Crosby、John R. Harding、Clare D. King、Gregory D. Parker、Christine L. Willis

  DOI：10.1021/ol020127o

  日期：2002.10.1

  [GRAPHICS]The first syntheses of two natural products, catechols 1 and 2, isolated from Plectranthus sylvestris (labiatae), are reported. Oxygen-18 labeling studies support the proposed intermediacy of a stabilized benzylic cation in the acid-promoted cyclization of an aldehyde and benzylic homoallylic alcohol possessing an electron-rich aromatic ring, In contrast, with an electron-deficient aromatic ring the pathway via a benzylic cation is only minor.