Acetaldehyde furfuryl 2-methoxyethyl acetal

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: Acetaldehyde furfuryl 2-methoxyethyl acetal
• 英文别名: 2-{[1-(2-methoxyethoxy)ethoxy]methyl}furan；2-{[1-(2-Methoxyethoxy)ethoxy]methyl}furan；2-[1-(2-methoxyethoxy)ethoxymethyl]furan
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: NGCMAPGSXHJSEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  糠醇 在 mercury(II) diacetate 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 Acetaldehyde furfuryl 2-methoxyethyl acetal
  参考文献：
  名称：

  Synthesis and biological activity of furanyl anti-juvenile hormonal compounds

  摘要：

  AbstractTwenty‐one synthetic compounds, containing one or more furan rings, were demonstrated to possess anti‐juvenile hormone (AJH) activity as evidenced by their induction of premature metamorphosis in the milkweed bug, Oncopeltus fasciatus (Dallas) by contact, topical application or fumigation. The ED50 of the four most active analogs required to induce precocious metamorphosis from 3rd‐instar nymphs by residue contact in a Petri dish compared favorably with that of precocene II (6,7‐dimethoxy‐2,2‐dimethyl 2H‐chromene) a naturally occurring phytochemical AJH. Precocious metamorphosis was fully reversible by co‐treatment with juvenile hormone (JH III) or JH analogs, demonstrating that the observed AJH activity resulted from an induced deficiency of juvenile hormone.

  DOI：

  10.1002/ps.2780430102

文献信息

• Nucleophilic addition to acetylenes in superbasic catalytic systems: XV. Vinylation of 2-hydroxymethylfuran
  作者：L. A. Oparina、O. V. Vysotskaya、A. V. Stepanov、I. V. Rodionova、G. F. Myachina、N. K. Gusarova、B. A. Trofimov

  DOI：10.1134/s1070428008010156

  日期：2008.1

  2-Hydroxymethylfuran reacted with acetylene in superbasic catalytic systems MOH-DMSO (M = Na, K) under mild temperature conditions (75–85°C, 1–2 h), yielding 80% of 2-vinyloxymethylfuran. The product, as well as acetaldehyde acetals derived therefrom, turned out to be promising as modifiers for electrolyte in lithium-sulfur rechargeable batteries.

  在温和的温度条件下（75-85°C，1-2小时），2-羟甲基呋喃与乙炔在超碱性催化体系MOH-DMSO（M = Na，K）中反应，生成80%的2-乙烯基氧甲基呋喃。该产物以及由此产生的乙醛缩醛有望成为锂硫可充电电池电解质的改性剂。
• Chemo- and regioselective reaction of vinyl furfuryl ethers with alcohols
  作者：L. A. Oparina、O. V. Vysotskaya、A. V. Stepanov、N. K. Gusarova、B. A. Trofimov

  DOI：10.1134/s1070428012090023

  日期：2012.9

  Furfuryl and tetrahydrofurfuryl vinyl ethers reacted with various alcohols under mild conditions (20-25A degrees C, 1-3 h, 1 wt % of CF3COOH) with high chemo- and regioselectivity to give the corresponding Markovnikov adducts at the vinyl group in up to 93% yield.
• Synthesis and biological activity of furanyl anti-juvenile hormonal compounds
  作者：William S. Bowers、Gopalan C. Unnithan、Jun-Ichi Fukushima、Jun Toda、Takeyoshi Sugiyama

  DOI：10.1002/ps.2780430102

  日期：1995.1

  AbstractTwenty‐one synthetic compounds, containing one or more furan rings, were demonstrated to possess anti‐juvenile hormone (AJH) activity as evidenced by their induction of premature metamorphosis in the milkweed bug, Oncopeltus fasciatus (Dallas) by contact, topical application or fumigation. The ED50 of the four most active analogs required to induce precocious metamorphosis from 3rd‐instar nymphs by residue contact in a Petri dish compared favorably with that of precocene II (6,7‐dimethoxy‐2,2‐dimethyl 2H‐chromene) a naturally occurring phytochemical AJH. Precocious metamorphosis was fully reversible by co‐treatment with juvenile hormone (JH III) or JH analogs, demonstrating that the observed AJH activity resulted from an induced deficiency of juvenile hormone.