1-(2-allyl-3,6-dimethoxyphenyl)ethanone | 174901-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-allyl-3,6-dimethoxyphenyl)ethanone
• 英文别名: 1-(3,6-Dimethoxy-2-prop-2-enylphenyl)ethanone
• CAS: 174901-52-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: TVXZVHDQZMSTCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  1-(2-allyl-3,6-dimethoxyphenyl)ethanone 在 sodium tetrahydroborate 、 copper(II) choride dihydrate 、 氧气 、 sodium ethanolate 、 palladium dichloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 ethyl 4-[3,6-dimethoxy-2-(2-oxopropyl)phenyl]-2-hydroxy-4-oxobutanoate
  参考文献：
  名称：

  Wacker oxidation methodology for the synthesis of the benzo-fused acetal core of marticin

  摘要：

  Methodology for the synthesis of the benzo-fused acetal core of marticin is described in this paper. Condensation of readily available 1-(2-allyl-3,6-dimethoxyphenyl)ethanone with diethyl oxalate under Claisen condensation conditions furnished (Z)-ethyl 4-(2-allyl-3,6-dimethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate. Treatment of this with LiAlH4 resulted in the formation of the diol, 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one. Conversion of primary alcohol of the diol into the TBDMS ether followed by further reaction with LiAlH4 and exposure to Wacker oxidation conditions resulted in the formation of (3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0(2.7)]trideca-2,4,6-trien-11-yl)methanol, the core of marticin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.052
• 作为产物：
  描述：

  1-(5-烯丙氧基-2-羟基苯基)-1-乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 42.0h， 生成 1-(2-allyl-3,6-dimethoxyphenyl)ethanone
  参考文献：
  名称：

  Wacker oxidation methodology for the synthesis of the benzo-fused acetal core of marticin

  摘要：

  Methodology for the synthesis of the benzo-fused acetal core of marticin is described in this paper. Condensation of readily available 1-(2-allyl-3,6-dimethoxyphenyl)ethanone with diethyl oxalate under Claisen condensation conditions furnished (Z)-ethyl 4-(2-allyl-3,6-dimethoxyphenyl)-2-hydroxy-4-oxobut-2-enoate. Treatment of this with LiAlH4 resulted in the formation of the diol, 1-(2-allyl-3,6-dimethoxyphenyl)-3,4-dihydroxybutan-1-one. Conversion of primary alcohol of the diol into the TBDMS ether followed by further reaction with LiAlH4 and exposure to Wacker oxidation conditions resulted in the formation of (3,6-dimethoxy-9-methyl-10,13-dioxatricyclo[7.3.1.0(2.7)]trideca-2,4,6-trien-11-yl)methanol, the core of marticin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.052

文献信息

• Weakly Coordinating, Ketone-Directed Cp*Co(III)-Catalyzed C–H Allylation on Arenes and Indoles
  作者：Md Raja Sk、Sourav Sekhar Bera、Modhu Sudan Maji

  DOI：10.1021/acs.orglett.7b03440

  日期：2018.1.5

  regioselective monoallylation of arenes and indoles is reported using a stable and cost-effective high-valent cobalt(III)-catalyst to access several important molecular building blocks. The allylation proceeds smoothly with a variety of substrates in the presence of various electron-rich and -deficient substituents. The method was applied to the formal synthesis of an ancisheynine alkaloid, a highly conjugated

  据报道，使用稳定且具有成本效益的高价钴（III）催化剂可对芳烃和吲哚进行弱配位，酮导向，区域选择性单烯丙基化反应，从而获得几种重要的分子结构单元。在存在各种富电子和不足电子的取代基的情况下，该烯丙基化作用与多种底物顺利进行。该方法被用于正式合成Anshesheynine生物碱，高度共轭的氮杂环丁烷和异色满。机理研究表明，烯丙基化反应遵循碱基辅助的分子间亲电取代途径。
• Carboxylic Acid Promoted, Redox‐Neutral Ru‐Catalyzed C−H Allylation of Aromatic Ketones
  作者：Dattatraya H. Dethe、Nagabhushana C. Beeralingappa、Balu D. Dherange

  DOI：10.1002/ejoc.202100717

  日期：2021.9.7

  ketone-directed C(sp2)−H allylation of aromatic ketones such as substituted acetophenones, 3-acetyl indoles, and chalcones was developed under redox-neutral conditions. 1-Adamantane carboxylic acid plays a crucial role in improving the reactivity of the [RuCl2(p-cymene)]2 catalyst at mild reaction temperatures. This method provides an access to various synthetically useful terminal olefin systems in moderate to good

  在氧化还原中性条件下开发了一种替代方法，用于芳族酮（如取代苯乙酮、3-乙酰吲哚和查耳酮）的弱配位、酮导向的 C(sp 2 )-H 烯丙基化。1-金刚烷羧酸在提高 [RuCl 2 (p-cymene)] 2催化剂在温和反应温度下的反应性方面起着至关重要的作用。该方法提供了以中等至良好产率获得各种合成有用的末端烯烃系统的途径。
• Synthesis of Some C‐4 Hydroxybenzo[<i>c</i>]pyrans: A New Approach
  作者：Victor I. Hugo、Tebogo Masenya、Ivan R. Green

  DOI：10.1080/00397910600592001

  日期：2006.6.1

  Abstract A new synthetic approach to the synthesis of some epimeric C‐4‐hydroxy‐benzo[c]pyrans is described. A key step in their formation is stereoisomerisation of a nonconjugated ortho alkenylphenylketone and ‐ester using palladium bisacetonitrile [bisacetonitriledichloropalladium(II)] to give the corresponding conjugated E stereoisomers which cyclize on treatment with meta‐chloroperbenzoic acid

  摘要描述了一种合成一些差向异构 C-4-羟基-苯并 [c] 吡喃的新合成方法。它们形成的关键步骤是使用双乙腈钯 [双乙腈二氯钯 (II)] 对非共轭邻烯基苯基酮和酯进行立体异构化，得到相应的共轭 E 立体异构体，该立体异构体在用间氯过苯甲酸 (m-CPBA) 处理后环化，得到目标化合物。
• A Case of Competitive Hydroboration
  作者：Robin G.F. Giles、Ivan R. Green

  DOI：10.1080/00397919608004624

  日期：1996.9

  Attempted chiral reduction of sterically crowded ketones 4 and 10 containing nonconjugated olefinic bonds with the Corey-Bakshi-Shibata (CBS) catalyst and diborane failed. However, products of olefinic hydration were isolated.

  尝试用 Corey-Bakshi-Shibata (CBS) 催化剂和乙硼烷手性还原含有非共轭烯烃键的空间拥挤的酮 4 和 10 失败。然而，分离出烯烃水合产物。
• 60. Studies in chelation. Part III. The stabilisation of kekulé forms in o-hydroxy-carbonyl compounds
  作者：Wilson Baker、O. M. Lothian

  DOI：10.1039/jr9360000274

  日期：——