1-(5-methylfuran-2-yl)pentan-1-one | 2349-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-methylfuran-2-yl)pentan-1-one
• 英文别名: 1-(5-methylfuran-2-yl)-1-pentanone
• CAS: 2349-16-8
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: YJWUSOPWBBNFLL-UHFFFAOYSA-N

物化性质

• LogP：
  2.570 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基三苯基碘化膦 、 1-(5-methylfuran-2-yl)pentan-1-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以85%的产率得到2-(hex-1-en-2-yl)-5-methylfuran
  参考文献：
  名称：

  Singlet-Oxygen-Mediated One-Pot Synthesis of 3-Keto-tetrahydrofurans from 2-(β-Hydroxyalkyl) Furans

  摘要：

  Photooxygenation of 2-(beta-hydroxyalkyl) furans affords, in one synthetic operation and in high yields, 3-keto-tetrhydrofuran motifs via intramolecular Michael-type addition to the 1,4-enedione intermediate.

  DOI：

  10.1021/ol8024742
• 作为产物：
  描述：

  1-(5-methylfuran-2-yl)pentan-1-ol 在 camphor-10-sulfonic acid 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 异辛烷 、 氯仿 为溶剂， 反应 4.0h， 生成 1-(5-methylfuran-2-yl)pentan-1-one
  参考文献：
  名称：

  叔丁基氢过氧化物的酸催化氧化呋喃衍生物

  摘要：

  叔丁基过氧化氢在酸催化下的异常反应性使得呋喃衍生物易于转化为3（6H）-吡喃酮。

  DOI：

  10.1016/s0040-4039(00)61606-4

文献信息

• Trialkylphosphine-Mediated Synthesis of 2-Acyl Furans from Ynenones
  作者：Chao Xu、Stéphane Wittmann、Manuel Gemander、Venla Ruohonen、J. Stephen Clark

  DOI：10.1021/acs.orglett.7b01533

  日期：2017.7.7

  A novel reaction for the synthesis of 2-acyl furans is reported. The reaction is believed to proceed by sequential addition of a trialkylphosphine to an ynenone, 5-exo-dig cyclization to form the furan, and oxidation of the resulting phosphonium ylide with molecular oxygen. Many common functional groups are tolerated during the reaction, and the products are obtained in good to excellent yield under

  报道了合成2-酰基呋喃的新反应。该反应被认为是通过依次加入三烷基膦的一种ynenone，5-进行外切-挖环化以形成呋喃，并用分子氧将所得磷叶立德的氧化。在反应过程中可以耐受许多常见的官能团，并且在温和的条件下以良好或优异的收率获得了产物。这种方法可以从简单的原料中有效地获得重要的生物化合物，包括稠合的多环化合物和呋喃甲醛。
• Gold Catalysis: Efficient 1,3-Induction with Diastereotopic Homopropargyl Alcohols in the Phenol Synthesis
  作者：A. Stephen K. Hashmi、Melissa Hamzić、Matthias Rudolph、Martin Ackermann、Frank Rominger

  DOI：10.1002/adsc.200900402

  日期：2009.10

  Furans with diastereotopic alkynyl groups were prepared and then converted to anellated phenols in gold-catalyzed reactions. In all cases a highly diastereoselective reaction was observed. The stereochemical outcome of the 1,3-induction could be assigned by two independent crystal structure analyses, showing a cis-arrangement of the two alkyl substituents on the benzoanellated cyclohexene ring.

  制备具有非对映异构炔基的呋喃，然后在金催化的反应中将其转化为芳基酚。在所有情况下，都观察到高度非对映选择性反应。1,3诱导的立体化学结果可以通过两个独立的晶体结构分析来确定，显示苯并芳香化的环己烯环上两个烷基取代基的顺式排列。
• TEMPO-Mediated Oxidation of Alcohols with Ion-Supported (Diacetoxyiodo)benzenes
  作者：Hideo Togo、Yusuke Suzuki、Masataka Iinuma、Katsuhiko Moriyama

  DOI：10.1055/s-0031-1290766

  日期：2012.5

  The oxidation of secondary alcohols and primary alcohols with novel ion-supported (diacetoxyiodo)benzenes (IS-DIB) in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidine-1-oxy radical (TEMPO) in dichloromethane at room temperature proceeded efficiently to provide the corresponding ketones and aldehydes, respectively, in good yields with high purity. Isolation of the product was easily

  在二氯甲烷中催化量的 2,2,6,6-四甲基哌啶-1-氧基（TEMPO）存在下，用新型离子负载（二乙酰氧基碘）苯（IS-DIB）氧化仲醇和伯醇在室温下进行有效地分别以高纯度的良好收率提供相应的酮和醛。通过简单的乙醚萃取反应混合物并随后从萃取物中除去溶剂，很容易实现产物的分离。此外，离子负载的碘苯是目前氧化中由 IS-DIB 衍生的副产物，以良好的收率回收，并且可以重新氧化为 IS-DIB，以便在相同的氧化中重复使用。
• Acid-catalyzed oxidation of furan derivatives by t-butyl hydroperoxide
  作者：Roberto Antonioletti、Luca Arista、Francesco Bonadies、Ludovica Locati、Arrigo Scettri

  DOI：10.1016/s0040-4039(00)61606-4

  日期：1993.10

  The unusual reactivity of t-butyl hydroperoxide under acid-catalysis allows the easy conversion of furan derivatives into 3(6H)-pyranones.

  叔丁基过氧化氢在酸催化下的异常反应性使得呋喃衍生物易于转化为3（6H）-吡喃酮。
• A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds
  作者：Antonella De Mico、Roberto Margarita、Luca Parlanti、Andrea Vescovi、Giovanni Piancatelli

  DOI：10.1021/jo971046m

  日期：1997.10.1

  Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are used in combination with [bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the conversion of primary and secondary alcohols to carbonyl compounds. This procedure works efficiently at room temperature in almost all common solvents and neat in some cases. This process exhibits a very high degree of selectivity for the oxidation of primary alcohols to aldehydes, without any noticeable overoxidation to carboxyl compounds, and a high chemoselectivity in the presence of either secondary alcohols or of other oxidizable moieties. This procedure allows an easy, convenient, high-yielding method for the oxidation of alcohols starting from commercially available compounds.