1-[4-(4-methoxyphenyl)-2-methyl-4,5-dihydrofuran-3-yl]ethanone | 1246175-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[4-(4-methoxyphenyl)-2-methyl-4,5-dihydrofuran-3-yl]ethanone
• 英文别名: 1-[3-(4-Methoxyphenyl)-5-methyl-2,3-dihydrofuran-4-yl]ethanone；1-[3-(4-methoxyphenyl)-5-methyl-2,3-dihydrofuran-4-yl]ethanone
• CAS: 1246175-29-0
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: MQPVYWVCNPVBJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-[4-(4-methoxyphenyl)-2-methyl-4,5-dihydrofuran-3-yl]ethanone 、 苯肼,盐酸盐 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以67%的产率得到2-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-2-(4-methoxyphenyl)ethanol
  参考文献：
  名称：

  多取代的吡唑和异恶唑的简单组件经由的3-酰基-4,5-二氢呋喃与肼和羟胺环合，开环反应多米诺†

  摘要：

  开发了一种方便的通用方法，该方法基于布朗斯台德酸引发的3-酰基-4,5-二氢呋喃与肼或羟胺的反应，制得2-（吡唑-4-基）-和2-（异恶唑-4-基）乙醇。阐述了在2-（吡唑基）乙醇中醇部分的进一步转化，提供了2-（吡唑基）乙胺作为有效的生物活性化合物以及抗肿瘤生物碱脆皮A的吡唑取代的衍生物。

  DOI：

  10.1039/c5ob02596f
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 1-[4-(4-methoxyphenyl)-2-methyl-4,5-dihydrofuran-3-yl]ethanone
  参考文献：
  名称：

  An efficient, transition-metal-free process for the synthesis of substituted dihydrofurans via a Michael/cyclization tandem reaction

  摘要：

  An efficient green route for the synthesis of substituted dihydrofurans was developed through a simple base-catalyzed, tandem reaction of nitrostyrene with 1,3-dicarbonyl compounds. The desired products were prepared with a large substrate scope and in excellent yields (up to 95%). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.151

文献信息

• Reaction of Corey Ylide with α,β-Unsaturated Ketones: Tuning of Chemoselectivity toward Dihydrofuran Synthesis
  作者：Alexey O. Chagarovsky、Ekaterina M. Budynina、Olga A. Ivanova、Elena V. Villemson、Victor B. Rybakov、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1021/ol500877c

  日期：2014.6.6

  A straightforward, efficient, and reliable approach to synthetically valuable 2,3-dihydrofurans via a reaction between Corey ylide and α,β-unsaturated ketones has been developed. The use of simple and widely spread starting materials as well as mild reaction conditions and scalability provide a broad scope of 2,3-dihydrofurans.

  通过Corey ylide与α，β-不饱和酮之间的反应，开发了一种合成有价值的2,3-二氢呋喃的简单，有效和可靠的方法。简单且广泛分布的起始原料的使用以及温和的反应条件和可扩展性提供了广泛的2,3-二氢呋喃范围。
• Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure–ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine
  作者：Alexey O. Chagarovskiy、Ekaterina M. Budynina、Olga A. Ivanova、Victor B. Rybakov、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1039/c5ob02596f

  日期：——

  A convenient general approach to 2-(pyrazol-4-yl)- and 2-(isoxazol-4-yl)ethanols based on the Brønsted acid-initiated reaction of 3-acyl-4,5-dihydrofurans with hydrazines or hydroxylamine was developed. Further transformation of the alcohol moiety in 2-(pyrazolyl)ethanols affording 2-(pyrazolyl)ethylamine as potent bioactive compounds as well as pyrazole-substituted derivatives of antitumor alkaloid

  开发了一种方便的通用方法，该方法基于布朗斯台德酸引发的3-酰基-4,5-二氢呋喃与肼或羟胺的反应，制得2-（吡唑-4-基）-和2-（异恶唑-4-基）乙醇。阐述了在2-（吡唑基）乙醇中醇部分的进一步转化，提供了2-（吡唑基）乙胺作为有效的生物活性化合物以及抗肿瘤生物碱脆皮A的吡唑取代的衍生物。
• An efficient, transition-metal-free process for the synthesis of substituted dihydrofurans via a Michael/cyclization tandem reaction
  作者：Ming-Yu Wu、Ming-Qi Wang、Kun Li、Xing-Wen Feng、Ting He、Na Wang、Xiao-Qi Yu

  DOI：10.1016/j.tetlet.2010.11.151

  日期：2011.2

  An efficient green route for the synthesis of substituted dihydrofurans was developed through a simple base-catalyzed, tandem reaction of nitrostyrene with 1,3-dicarbonyl compounds. The desired products were prepared with a large substrate scope and in excellent yields (up to 95%). (C) 2010 Elsevier Ltd. All rights reserved.