methyl (3-methylfuran-2-yl)acetate | 149694-49-5

• 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: methyl (3-methylfuran-2-yl)acetate
• 英文别名: methyl 2-(3-methylfur-2-yl)acetate；methyl 3-methyl-2-furanacetate；Methyl (3-methyl-2-furyl)acetate；methyl 2-(3-methylfuran-2-yl)acetate
• CAS: 149694-49-5
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: DYAIHBLTSGWBOR-UHFFFAOYSA-N

物化性质

• 沸点：
  195.6±25.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (3-methylfuran-2-yl)acetate 在 sodium tetrahydroborate 、 N,N-二甲基甲酰胺二新戊基乙缩醛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 3-甲基-2-(3-甲基-2-丁烯基)呋喃
  参考文献：
  名称：

  Synthesis of rosefuran. A new route to furans through base-catalyzed cyclization of hydroxy alkynoates and alkynones

  摘要：

  A new synthesis of furans involving intramolecular 1,4-addition of (Z)-6-hydroxy 4-en-2-ynoates and ynones has been developed and applied to a total synthesis of rosefuran.

  DOI：

  10.1021/jo00066a003
• 作为产物：
  描述：

  (Z)-3-甲基戊-2-烯-4-炔-1-醇 在 正丁基锂 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 methyl (3-methylfuran-2-yl)acetate
  参考文献：
  名称：

  Synthesis of rosefuran. A new route to furans through base-catalyzed cyclization of hydroxy alkynoates and alkynones

  摘要：

  A new synthesis of furans involving intramolecular 1,4-addition of (Z)-6-hydroxy 4-en-2-ynoates and ynones has been developed and applied to a total synthesis of rosefuran.

  DOI：

  10.1021/jo00066a003

文献信息

• Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis
  作者：Violet Yijang Chen、Ohyun Kwon

  DOI：10.1002/anie.202015232

  日期：2021.4.12

  the construction of tetraalkyl furans remains non‐trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine‐palladium catalysis, for the preparation of various polyalkyl furans from readily

  多烷基呋喃在自然界中广泛存在，通常发挥重要的生物学作用。尽管合成四取代呋喃的方法有很多，但四烷基呋喃的构建仍然很重要。生物活性呋喃天然产物中烷基的普遍存在，加上四烷基呋喃所需的生物活性，需要一种多烷基呋喃的通用合成方案。本文描述了一种 Michael-Heck 方法，使用顺序膦-钯催化，从容易获得的前体制备各种聚烷基呋喃。该方法的多功能性通过属于不同类别的九种不同的多烷基化呋喃天然产物（即呋喃萜玫瑰呋喃、倍半糖呋喃和米卡尼呋喃）的全合成来说明；海洋天然产物plakorsin A、B、D和plakorsin D甲酯；以及呋喃脂肪酸3D5和氢木霉素。
• Synthesis of Functionalized Furans Based on a ‘[3+2] Cyclization/Bromination­/Elimination’ Strategy
  作者：Peter Langer、Esen Bellur

  DOI：10.1055/s-2006-926301

  日期：——

  The bromination of 2-alkylidenetetrahydrofurans -readily available via one-pot [3+2] cyclizations - afforded 2-alkylidene-3-bromotetrahydrofurans. Elimination of hydrogen bromide and subsequent aromatization of these compounds provided a convenient approach to functionalized furans.

  2-亚烷基四氢呋喃的溴化-通过一锅[3+2]环化很容易获得-得到2-亚烷基-3-溴四氢呋喃。溴化氢的消除和这些化合物的随后芳构化为官能化呋喃提供了一种方便的方法。
• Regioselective Synthesis of Functionalized Furans by Cyclization of 1,3-Bis-Silyl Enol Ethers with 1-Chloro-2,2-dimethoxyethane
  作者：Esen Bellur、Helmar Görls、Peter Langer

  DOI：10.1002/ejoc.200400805

  日期：2005.5

  Cyclization of 1,3-bis-silyl enol ethers with 1-chloro-2,2-dimethoxyethane allowed an efficient, regio- and diastereoselective synthesis of a variety of 2-alkylidene-4-methoxytetrahydrofurans. The TFA-mediated elimination of methanol resulted in the formation of functionalized furans. Similarly, 2,3,3a,4,5,6-hexahydro-2,3-benzofurans were prepared and transformed into 4,5,6,7-tetrahydro-2,3-benzofurans

  1,3-双-甲硅烷基烯醇醚与 1-氯-2,2-二甲氧基乙烷的环化允许高效、区域和非对映选择性合成各种 2-亚烷基-4-甲氧基四氢呋喃。TFA 介导的甲醇消除导致功能化呋喃的形成。类似地，制备了 2,3,3a,4,5,6-六氢-2,3-苯并呋喃，并通过用 TFA 处理转化为 4,5,6,7-四氢-2,3-苯并呋喃。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Efficient synthesis of functionalized furans and benzofurans based on a ‘[3+2] cyclization/oxidation’ strategy
  作者：Esen Bellur、Ilia Freifeld、Peter Langer

  DOI：10.1016/j.tetlet.2005.02.040

  日期：2005.3

  Functionalized furans and benzofurans were prepared by DDQ oxidation of 2-alkylidenetetrahydrofurans, which are readily available by one-pot cyclizations of 1,3-dicarbonyl dianions or 1,3-bis-silyl enol ethers.

  通过2-亚烷基四氢呋喃的DDQ氧化制备官能化的呋喃和苯并呋喃，这可以通过一锅式环合1,3-二羰基二价阴离子或1,3-双-甲硅烷基烯醇醚而容易获得。
• Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives
  作者：Marcelo E. Piotti、Howard Alper

  DOI：10.1021/jo971303n

  日期：1997.11.1

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.