2-(3-methoxy-prop-1-ynyl)-phenol | 259739-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3-methoxy-prop-1-ynyl)-phenol
• 英文别名: 2-(3-Methoxyprop-1-ynyl)phenol
• CAS: 259739-71-4
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: OVNNKIMQEABVAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酰乙酸甲酯 、 2-(3-methoxy-prop-1-ynyl)-phenol 在 magnesium chloride 、 Zeise's dimer 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.25h， 以63%的产率得到C₁₄H₁₄O₄
  参考文献：
  名称：

  Lewis Acid Mediated Vinylogous Additions of Enol Nucleophiles into an α,β-Unsaturated Platinum Carbene

  摘要：

  A variety of substituted indoles and benzofurans are accessed via a platinum catalyzed annulation and vinylogous addition of enol nudeophiles. Several beta-dicarbonyl compounds participate in the reaction, as do alpha-nitro and alpha-cyano carbonyl species. Subjecting the indole products to acidic conditions results in the formation of fused heterocycles.

  DOI：

  10.1021/acs.orglett.5b03246
• 作为产物：
  描述：

  1-乙酰氧基-2-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 肼 作用下， 生成 2-(3-methoxy-prop-1-ynyl)-phenol
  参考文献：
  名称：

  Novel Pd^II-Mediated Cascade Carboxylative Annulation to Construct Benzo[b]furan-3-carboxylic Acids

  摘要：

  Benzo[b]furan-3-carboxylic acid (2) was generated from 1 by forming three new bonds in one step via a Pd-II-mediated cascade carboxylative annulation. The proposed mechanism was supported by the observation of an unusual acetylation of 1 as a side reaction together with an O-18-labeling study.

  DOI：

  10.1021/ol050876g

文献信息

• Cationic Palladium(II)-Catalyzed Synthesis of 2-Substituted 3-Hydroxymethylbenzo[b]furans
  作者：Xiuling Han、Xiyan Lu、Huan Wang

  DOI：10.1055/s-0030-1289519

  日期：2011.10

  tandem reaction involving an intramolecular oxypalladation of an alkyne and an addition to the carbonyl group to quench the carbon-palladium bond to complete the catalytic cycle was developed. The reaction was catalyzed with the cationic palladium(II) species without the necessity of a redox system. aldehyde - alkyne - cationic palladium(II) complex - 3-hydroxymethylbenzofuran - oxypalladation

  开发了一种串联反应，该反应涉及炔烃的分子内氧化钯和加成羰基以淬灭碳-钯键以完成催化循环。该反应用阳离子钯（II）物种催化，无需氧化还原系统。 醛-炔烃-阳离子钯（II）配合物-3-羟甲基苯并呋喃-氧化钯
• Platinum(II)-Catalyzed Generation and [3+2] Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates for the Preparation of Polycyclic Compounds
  作者：Kodai Saito、Hideyuki Sogou、Takuya Suga、Hiroyuki Kusama、Nobuharu Iwasawa

  DOI：10.1021/ja108586d

  日期：2011.2.2

  Pt(II)-catalyzed generation of unsaturated carbene complex intermediates from various propargyl ether derivatives based on electrophilic activation of alkynes was realized. These in situ generated unsaturated carbene complexes undergo [3+2] cycloaddition reaction with various vinyl ethers, leading to efficient formation of indoles, naphthols, and benzofuran fused with a five-membered ring in high yields

  基于炔烃的亲电活化，实现了 Pt(II) 催化从各种炔丙基醚衍生物生成不饱和卡宾配合物中间体。这些原位生成的不饱和卡宾配合物与各种乙烯基醚发生 [3+2] 环加成反应，从而以高产率有效形成与五元环稠合的吲哚、萘酚和苯并呋喃。
• A New Complex of Palladium−Thiourea and Carbon Tetrabromide Catalyzed Carbonylative Annulation of <i>o</i>-Hydroxylarylacetylenes:  Efficient New Synthetic Technology for the Synthesis of 2,3-Disubstituted Benzo[<i>b</i>]furans
  作者：Yang Nan、Hua Miao、Zhen Yang

  DOI：10.1021/ol991327b

  日期：2000.2.1

  [GRAPHICS]A highly effective cocatalysis system (Pdl(2)-thiourea and CBr4) was developed for carbonylative cyclization of bath electron-rich and electron-deficient o-hydroxylarylacetylenes to the corresponding methyl benzo[b]furan-3-carboxylates.