3-methylene-5-propyldihydrofuran-2(3H)-one | 58557-30-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-methylene-5-propyldihydrofuran-2(3H)-one
• 英文别名: 3-methylene-5-propyltetrahydrofuran-2-one；α-methylene-γ-heptalactone；4-n-propyl-2-methylenebutyrolactone；3-methylene-5-propyl-dihydro-furan-2-one；3-Methylidene-5-propyloxolan-2-one
• CAS: 58557-30-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: RYUTXWGSEWCLCG-UHFFFAOYSA-N

物化性质

• 沸点：
  249.3±19.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙位庚内酯 在 吡啶 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 10.0h， 生成 3-methylene-5-propyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and Biological Activity of α-Methylene-γ-lactones as New Aroma Chemicals

  摘要：

  Seven kinds of alpha -methylene-gamma -lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28-34%. These alpha -methylene-gamma -lactones had characteristic and unique odors. All alpha -methylene-gamma -lactones added a roast-like odor to materials. The antimicrobial effects of alpha -methylene-gamma -lactones were investigated by using a paper disk diffusion method. The results showed the alpha -methylene-gamma -lactones inhibited the growth of three bacteria (Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, alpha -methylene-gamma -undecalactone and alpha -methylene-gamma -dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl p-hydroxybenzoate as standard antibiotic. The umu test revealed that the alpha -methylene-gamma -lactones suppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation and Trp-P-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by alpha -methylene-gamma -lactones had a tendency to intensify as the number of carbons in the side chain increased.

  DOI：

  10.1021/jf000346t

文献信息

• Concise syntheses of 3-methylenetetrahydrofuran-2-one derivatives and related systems
  作者：Robert M. Adlington、Anthony G. M. Barrett

  DOI：10.1039/p19810002848

  日期：——

  Using the Shapiro reaction, the title compounds were prepared in ‘one pot’ from the condensation of two ketones, or an aldehyde and a ketone, with carbon dioxide. For example, acetone 2,4,6-tri-isopropylbenzenesulphonylhydrazone was treated in sequence with n-butyl-lithium (–50 °C), acetone (–50 °C), n-butyl-lithium (–78 to 0 to –78 °C), carbon dioxide (–78 °C), and trifluoroacetic acid (25 °C) to

  使用Shapiro反应，由两个酮或醛和酮与二氧化碳缩合，在“一锅”中制备标题化合物。例如，依次用正丁基锂（–50°C），丙酮（–50°C），正丁基锂（–78至0至– 78°C），二氧化碳（–78°C）和三氟乙酸（25°C）生成5,5-二甲基-3-亚甲基四氢呋喃-2-酮。扩展反应以制备3-亚甲基四氢吡喃-2-酮和3，5-二亚甲基四氢呋喃-2-酮的衍生物。
• A New Synthesis of <b><i>exo</i></b>-Methylene Butyrolactones from Nitroalkanes
  作者：Roberto Ballini、Giovanna Bosica、Damiana Livi

  DOI：10.1055/s-2001-16098

  日期：——

  A versatile route to exo-methylene butyrolactones was developed by employing a three step reaction sequence consisting of Michael addition of primary nitroalkanes 1 to ethyl (2-bromomethyl)acrylate (2), then Nef conversion of the nitro derivatives 3, and subsequent lactonization of the obtained keto esters 4. The method is chemoselective for important functionalities such as ester, C=C double bond and hydroxyl.

  开发了一种多功能的路线用于exo-亚甲基丁内酯，通过采用三步反应序列实现，首先是将一烷基硝基烷1与乙基(2-溴甲基)丙烯酸酯2进行迈克尔加成，然后对得到的硝基衍生物3进行内夫转化，最后对所获得的酮酯4进行内酯化。该方法对酯、C=C双键和羟基等重要官能团具有化学选择性。
• Tandem Ene-Reaction/Intramolecular Sakurai Cyclisation (IMSC): A Novel Access to Polysubstituted Tetrahydropyrans and γ-Butyrolactones Using a Unique Allylation Strategy
  作者：István E. Markó、Raphaël Dumeunier、Cédric Leclercq、Bernard Leroy、Jean-Marc Plancher、Abdelaziz Mekhalfia、Daniel J. Bayston

  DOI：10.1055/s-2002-28506

  日期：——

  The ene-reaction between a variety of aldehydes and allylsilane 22 generates highly functionalised homoallylic alcohols 23. These adducts undergo a subsequent Intramolecular Sakurai Cyclisation (IMSC), affording in good yields polysubstituted tetrahydropyran derivatives. Furthermore, oxidative desilylation of 23 provides an efficient, connective access to a range of γ-butyrolactones and α-methylene-γ-butyrolactones.

  各种醛和烯丙基硅烷 22 之间的烯反应生成高度官能化的均烯丙基醇 23。这些加合物在随后的分子内樱井环化（IMSC）反应中，可以得到收率很高的多取代四氢吡喃衍生物。此外，对 23 进行氧化脱硅处理，可以高效地连接到一系列 δ³ 丁内酯和 δ±-亚甲基-δ³-丁内酯。
• Oxidation of 2-substituted allylsilane to conjugated enal using hypervalent organoiodine compound and synthesis of α-methylen γ-and δ-lactones
  作者：Masahito Ochiai、Eiichi Fujita、Masao Arimoto、Hideo Yamaguchi

  DOI：10.1016/s0040-4039(00)81525-7

  日期：1983.1

  2-Substituted allylsilanes on treatment with iodosbenzene and boron trifluoride etherate in dioxane afforded conjugated enals directly in good yield, from which α-methylen γ- and δ-lactones were synthesized.

  在二恶烷中用碘代苯和三氟化硼醚化物处理的2-取代的烯丙基硅烷可直接以良好的收率得到共轭烯醛，由此合成α-亚甲基γ-和δ-内酯。
• Concise and connective synthesis of exo-methylene-γ-butyrolactones
  作者：Raphaël Dumeunier、Cédric Leclercq、István E Markó

  DOI：10.1016/s0040-4039(02)00240-x

  日期：2002.3

  A novel sequence, combining an ene-reaction of the substituted allylsilane 2 with a variety of aldehydes, followed by an oxidative double desilylation, provides an efficient access to a wide range of exo-methylene-γ-butyrolactones.

  一种新颖的序列，将取代的烯丙基硅烷2的烯反应与各种醛结合，然后进行氧化性双甲硅烷基化反应，可以有效地获得广泛的外-亚甲基-γ-丁内酯。