4,6,6-三甲基-5,6-二氢-2H-吡喃-2-酮 | 6970-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4,6,6-三甲基-5,6-二氢-2H-吡喃-2-酮
• 英文名称: 4,6,6-trimethyl-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4,6,6-Trimethyl-5,6-dihydro-2H-pyran-2-on；4,6,6-trimethyl-5,6-dihydropyran-2-one；4,6,6-trimethyl-5,6-dihydro-pyran-2-one；4,6,6-Trimethyl-5,6-dihydro-pyran-2-on；Dimethyl-3,5-hydroxy-5-hexen-2-carbonsaeure-δ-lacton；3.5-Dimethyl-Δ²-hexenolid-(1.5)；2,2,4-trimethyl-3H-pyran-6-one
• CAS: 6970-56-5
• 化学式: C₈H₁₂O₂
• mdl: MFCD00085431
• 分子量: 140.182
• InChiKey: ZSQHRLJAKWRVJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  30 °C
• 沸点：
  104 °C(Press: 4 Torr)
• 密度：
  0.996 g/cm3(Temp: 25 °C)
• 保留指数：
  1905

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6,6-三甲基-5,6-二氢-2H-吡喃-2-酮 以54%的产率得到
  参考文献：
  名称：

  BARDILI, B.;MARSCHALL-WEYERSTAHL, H.;WEYERSTAHL, P., LIEBIGS ANN. CHEM., 1985, N 2, 275-300

  摘要：

  DOI：
• 作为产物：
  描述：

  二丙酮醇 在 正丁基锂 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.67h， 生成 4,6,6-三甲基-5,6-二氢-2H-吡喃-2-酮
  参考文献：
  名称：

  Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones

  摘要：

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.

  DOI：

  10.1021/ol401824v

文献信息

• Studies towards a total synthesis of kainic acid
  作者：E.S Greenwood、P.B Hitchcock、P.J Parsons

  DOI：10.1016/s0040-4020(03)00425-3

  日期：2003.4

  The preparation of the fused bicycle 14 is reported together with its photocyclisation to the dioxinone 2. Base induced fragmentation of the photoadduct 15 formed exclusively in the aforementioned photocylisation, followed by Wittig methylenation gave the kainoid derivative 18.

  据报道，融合自行车14的制备及其与二恶英酮2的光环化作用。碱诱导的仅在上述光环化反应中形成的光加合物15发生断裂，然后进行Wittig亚甲基化，得到了类胡萝卜素衍生物18。
• A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group
  作者：A.J. Bloodworth、Brian D Bothwell、Andrew N Collins、Nicola L Maidwell

  DOI：10.1016/0040-4039(96)00143-8

  日期：1996.3

  Natural and unnatural analogues 4 of plakinic acids A, C and D have been prepared in three steps from alkan-2-ones by (i) LDA-induced condensation with ethyl 3-methylbut-2-enoate to give (2Z)-3,5-dimethylalka-2,4-dienoic acids 10, then (ii) isomerisation to the 2E-isomers 5 and finally (iii) peroxymercuriation with 30% hydrogen peroxide and reduction in situ with sodium borohydride.

  al酸A，C和D的天然和非天然类似物4已通过三步法从烷烃-2-酮制备，方法是：（i）LDA诱导与3-甲基丁-2-烯酸乙酯缩合，得到（2Z）-3， 5-二甲基-2,4-二烯酸10，然后（ii）异构化为2 E-异构体5，最后（iii）用30％过氧化氢进行过氧汞化，并用硼氢化钠原位还原。
• Photocyclodimerization of 5-Methyl-2<i>H</i>-pyran-3(6<i>H</i>)-one
  作者：Ljubov Groesch、Jürgen Kopf、Paul Margaretha

  DOI：10.1002/hlca.200890239

  日期：2008.12

  The structures of the main products resulting from photocyclodimerization of the title compound 2 and of other 3-methyl-substituted ‘oxacyclohex-2-en-1-ones’ (=dihydropyranones) were determined by X-ray crystallography. In connection, the 13C-NMR chemical shifts of the cyclobutane C-atoms of these dimers allow a clear differentiation between head-to-head and head-to-tail regioisomers, all structurally

  由标题化合物2和其他3-甲基取代的“氧杂环己-2-烯-1-酮”（＝二氢吡喃酮）的光环二聚作用产生的主要产物的结构通过X射线晶体学测定。与此相关，这些二聚体的环丁烷C原子的13 C-NMR化学位移可实现头对头和头对尾区域异构体之间的清晰区分，所有这些结构异构体均与异佛尔酮（1）相关。
• Alternative Synthesis of 2-Hydroxy-3,5,5-trimethylcyclopent-2-en-1-one
  作者：Christian Chapuis、Christine Saint-Léger

  DOI：10.1002/hlca.200900231

  日期：2010.1

  AbstractThe 2‐hydroxy‐3,5,5‐trimethylcyclopent‐2‐en‐1‐one (1) was synthesized in 42% yield by rearrangement of epoxy ketone 10 on treatment with BF3⋅Et2O under anhydrous conditions. Intermediate 10 was available from the known enone 8, either via direct epoxidation (60% H2O2, NaOH, MeOH; yield 50%), or via reduction to the corresponding allylic alcohol 14 (LiAlH4, THF), followed by epoxidation ([VO(acac)2], tBuOOH) and reoxidation under Swern conditions, in 37% total yield.
• Selective .gamma.-substitution of .alpha.,.beta.-unsaturated esters via .alpha.-trimethylsilyl .beta.,.gamma.-unsaturated esters
  作者：Pamela Albaugh-Robertson、John A. Katzenellenbogen

  DOI：10.1021/jo00174a026

  日期：1983.12

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