β-methyl-γ-(2-furyl)allyl alcohol | 69978-22-9

• 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: β-methyl-γ-(2-furyl)allyl alcohol
• 英文别名: (e)-3-(Furan-2-yl)-2-methylprop-2-en-1-ol；3-(furan-2-yl)-2-methylprop-2-en-1-ol
• CAS: 69978-22-9
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: CETHPBHBZHLYOY-UHFFFAOYSA-N

物化性质

• 沸点：
  235.8±20.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 β-methyl-γ-(2-furyl)allyl alcohol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 3-(2-Furyl)-2-methylallyl acetate
  参考文献：
  名称：

  Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates

  摘要：

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.

  DOI：

  10.1021/jo00005a046
• 作为产物：
  描述：

  糠醛 在 sodium 、 二异丁基氢化铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 17.0h， 生成 β-methyl-γ-(2-furyl)allyl alcohol
  参考文献：
  名称：

  Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates

  摘要：

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.

  DOI：

  10.1021/jo00005a046

文献信息

• Ir nanoclusters confined within hollow MIL-101(Fe) for selective hydrogenation of α,β-unsaturated aldehyde
  作者：Qinglin Liu、Qian Liu、Yurong Chen、Yinle Li、Hui Su、Qinghua Liu、Guangqin Li

  DOI：10.1016/j.cclet.2021.06.047

  日期：2022.1

  Although the selective hydrogenation of α,β-unsaturated aldehyde to unsaturated alcohol (UOL) is an extremely important transformation, it is still a great challenge to achieve high selectivity to UOL due to thermodynamic favoring of the C=C hydrogenation over the C=O hydrogenation. Herein, we report that iridium nanoclusters (Ir NCs) confined within hollow MIL-101(Fe) expresses satisfied reaction

  尽管α,β-不饱和醛选择性加氢为不饱和醇（UOL）是一个极其重要的转化，但由于热力学上C=C加氢比C=O更偏向于实现对UOL的高选择性仍然是一个巨大的挑战氢化。在此，我们报告限制在空心 MIL-101(Fe) 内的铱纳米团簇 (Ir NCs) 表现出令人满意的反应活性 (93.9%) 和高选择性 (96.2%) 肉桂醛 (CAL) 氢化成肉桂醇 (COL) 下1 巴 H 2大气和室温。MIL-101(Fe) 独特的空心结构有利于反应物的快速传输，确保 Ir@MIL-101(Fe) 与 MIL-101 表面的 Ir NCs 相比具有可比的反应活性和更好的可回收性(铁)。此外，X 射线光电子能谱数据表明正电性 Ir NCs，由于电子从 Ir 转移到 MIL-101(Fe)，可以与氧孤对相互作用，傅立叶变换红外光谱显示 MIL- 101(Fe) 可以与 C=O 键强烈相互作用，这有助于 COL 的高选择性。这项工作表明中空
• Effective and Selective Catalysts for Cinnamaldehyde Hydrogenation: Hydrophobic Hybrids of Metal-Organic Frameworks, Metal Nanoparticles, and Micro- and Mesoporous Polymers
  作者：Kuo Yuan、Tianqun Song、Dawei Wang、Xiaotao Zhang、Xiong Gao、Ye Zou、Huanli Dong、Zhiyong Tang、Wenping Hu

  DOI：10.1002/anie.201801289

  日期：2018.5.14

  Metal–organic frameworks (MOFs) as selectivity regulators for catalytic reactions have attracted much attention, especially MOFs and metal nanoparticle (NP) shelled structures, e.g., MOFs@NPs@MOFs. Nevertheless, making hydrophilic MOF shells for gathering hydrophobic reactants is challenging. Described here is a new and viable approach employing conjugated micro‐ and mesoporous polymers with iron(III)

  金属有机骨架（MOF）作为催化反应的选择性调节剂已经引起了广泛的关注，特别是MOF和金属纳米颗粒（NP）带壳结构，例如MOFs @ NPs @ MOFs。然而，制造用于收集疏水性反应物的亲水性MOF壳具有挑战性。本文介绍了一种新的可行方法，该方法将共轭微孔和中孔聚合物与卟啉铁（III）（FeP-CMP）用作制造MIL-101 @ Pt @ FeP-CMP的新壳体。它不仅是疏水的和多孔的，用于富集反应物，而且还具有激活C = O键的铁位，从而调节肉桂醛加氢中肉桂醇的选择性。有趣的是，MIL-101 @ Pt @ FeP-CMP海绵可以实现较高的周转频率（1516.1 h -1），对肉桂醇的选择性为97.3％，转化率为97.6％。
• Reactions of furan aldehydes 4. Oxidation-reduction reactions of furfural with monohydric alcohols
  作者：Yu. M. Shapiro

  DOI：10.1007/bf00528631

  日期：1993.1
• Construction of polycyclic compounds by cyclocarbonylation. 6. Palladium-catalyzed cyclocarbonylation of 3-(heteroaryl)allyl acetates
  作者：Masakazu Iwasaki、Yoshihiro Kobayashi、Ji Ping Li、Hiroyuki Matsuzaka、Youichi Ishii、Masanobu Hidai

  DOI：10.1021/jo00005a046

  日期：1991.3

  Acetoxybenzofurans, acetoxybenzothiophenes, acetoxyindoles, and acetoxycarbazoles were obtained in high yields by cyclocarbonylation of 3-furyl-, 3-thienyl-, 3-pyrrolyl-, and 3-indolylallyl acetates, respectively, in the presence of Ac2O, NEt3, and a catalytic amount of PdCl2(PPh3)2 at 130-170-degrees-C under 50-70 atm of CO. 3-(3-Furyl)allyl and 3-(3-thienyl)allyl acetates cyclized selectively at the 2-position of the heterocyclic nucleus to give 7-acetoxybenzofuran and 7-acetoxybenzothiophene, respectively. The synthetic utility of the reaction was demonstrated by the synthesis of cannabifuran from isothymol.