α-methylene-γ-hexalactone | 67964-41-4

• 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: α-methylene-γ-hexalactone
• 英文别名: 4,5-dihydro-5-ethyl-3-methylene-2(3H)-furanone；5-ethyl-3-methylenetetrahydrofuran-2-one；4-ethyl-2-methylenebutyrolactone；5-ethyl-3-methylenedihydrofuran-2(3H)-one；γ-ethyl-α-methylene-γ-butyrolactone；5-ethyl-3-methylene-dihydro-furan-2-one；5-ethyl-3-methylideneoxolan-2-one
• CAS: 67964-41-4
• 化学式: C₇H₁₀O₂
• mdl: MFCD09030735
• 分子量: 126.155
• InChiKey: FXWWAVREXBDOSP-UHFFFAOYSA-N

物化性质

• 沸点：
  41-45 °C(Press: 0.2 Torr)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 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：

  γ-己内酯 在 吡啶 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 10.0h， 生成 α-methylene-γ-hexalactone
  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。
• POLYMERIZABLE COMPOUNDS AND USE THEREOF IN LIQUID CRYSTAL DISPLAYS
  申请人：Taugerbeck Andreas

  公开号：US20130093975A1

  公开（公告）日：2013-04-18

  The present invention relates to polymerisable compounds, to processes and intermediates for the preparation thereof, and to the use thereof for optical, electro-optical and electronic purposes, in particular in liquid-crystal (LC) media and LC displays, especially in LC displays of the PS (“polymer sustained”) or PSA (“polymer sustained alignment”) type.

  本发明涉及可聚合化合物，以及用于其制备的工艺和中间体，以及其在光学、电光和电子方面的用途，特别是在液晶（LC）介质和LC显示器中的应用，特别是在PS（“聚合物持续”）或PSA（“聚合物持续取向”）类型的LC显示器中的应用。
• General synthesis of exomethylene-α-lactones via the retro-diels-alder reaction
  作者：Akitami Ichihara、Noriki Nio、Sadao Sakamura

  DOI：10.1016/s0040-4039(00)92202-0

  日期：——

  New synthetic methods of tulipalin A were deviced via the retro-Diels-Alder reaction and the generality was demonstrated by the synthesis of several α-methylene-α-alkyl-α-butyrolactones.

  通过逆Diels-Alder反应，制备了新的tulipalin A合成方法，并通过合成几种α-亚甲基-α-烷基-α-丁内酯证明了其普遍性。
• Lithiated Dimethylketene Diisopropyl Dithioacetal as a Synthon of Homoenolate Dianion of Isobutyric Ester. An Application to the Synthesis of α-Methylenelactones
  作者：Tamotsu Fujisawa、Kazuto Umezu、Masahiro Suzuki、Toshio Sato

  DOI：10.1246/cl.1986.1675

  日期：1986.10.5

  diisopropyl dithioacetal reacted with various kinds of electrophiles to afford γ-substituted products with high regioselectivity. The utility of the lithiated ketene dithioacetal, a novel homoenolate dianion equivalent of isobutyric ester, was demonstrated in the synthesis of α-methylenelactones.

  二甲基乙烯酮二异丙基二硫缩醛的锂阴离子与各种亲电试剂反应得到具有高区域选择性的γ-取代产物。在α-亚甲基内酯的合成中证明了锂化乙烯酮二硫缩醛的效用，这是一种新型的异丁酸酯的均烯醇二阴离子等价物。
• Palladium(II)-Catalyzed Aerobic Intermolecular Cyclization of Acrylic Acid with Alkenes to α-Methylene-γ-butyrolactones
  作者：Koji Yonehara、Yasuyuki Miyoshi、Aki Tsukajima、Takeo Akatsuka、Makoto Saito

  DOI：10.1002/adsc.201100006

  日期：2011.5.9

  this article is a palladium(II)/copper(II)‐ or palladium(II)‐catalyzed intermolecular cyclization of acrylic acid with alkenes to produce α‐methylene‐γ‐butyrolactone derivatives using molecular oxygen as an environmentally benign oxidant. In this system, the carboxylato, especially trifluoroacetato, or trimethylacetato ligand, plays a quite important role to afford a high catalytic activity by suppressing

  本文中的方法是钯（II）/铜（II）-或钯（II）与烯烃的丙烯酸分子间环化反应，利用分子氧作为环境友好的氧化剂生产α-亚甲基-γ-丁内酯衍生物。在此系统中，羧基，尤其是三氟乙酰基或三甲基乙酰基配体，在抑制钯（0）黑色沉积方面发挥着非常重要的作用，以提供高催化活性。