3-methoxy-2-methylcyclopent-2-enone | 3883-56-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 3-methoxy-2-methylcyclopent-2-enone
• 英文别名: 3-methoxy-2-methyl-2-cyclopenten-1-one；3-methoxy-2-methylcyclopent-2-en-1-one；2-methyl-3-methoxy-2-cyclopentenone；3-methoxy-2-methyl-2-cyclopentenone
• CAS: 3883-56-5
• 化学式: C₇H₁₀O₂
• mdl: MFCD18813865
• 分子量: 126.155
• InChiKey: UNOGKKKQILBOFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  3-methoxy-2-methylcyclopent-2-enone 在 dicobalt octacarbonyl 作用下， 反应 1.0h， 生成 cis,anti,cis-1-methoxy-7-methyl-endo-8-hydroxytricyclo<5.3.0.0^2,6>dec-4-en-3-one
  参考文献：
  名称：

  Cobalt-based route to highly functionalized hydrazulenes

  摘要：

  DOI：

  10.1021/jo00392a019
• 作为产物：
  描述：

  甲醇 、 3-氯-2-甲基环戊-2-烯酮 在 potassium carbonate 作用下， 反应 18.0h， 以74%的产率得到3-methoxy-2-methylcyclopent-2-enone
  参考文献：
  名称：

  Reaction of Phosphonate-Stabilized Carbanions with Cyclic Enones Bearing a .beta.-Leaving Group

  摘要：

  Reaction between alpha-lithiated alkylphosphonic esters and alpha,beta-unsaturated cyclopentenones and cyclohexenones carrying a heteroatom substituent Y in the beta-position was studied. Complete chemoselectivity was observed as a function of substituent Y. For Y = OMe exclusive addition-elimination at the beta-carbon was observed, yielding alpha,beta-unsaturated delta-ketophosphonates. The beta-chloro-substituted substrates (Y = Cl) derived from cyclohexenone reacted exclusively at the carbonyl carbon, yielding (2-hydroxyalkyl)phosphonates with the retained chlorovinyl function. The alcohols, depending on the conditions, could be dehydrated to two different products. The reaction of 3-chlorocyclopent-2-en-1-one with diethyl (lithiomethyl)phosphonate occurred at the beta-carbon, but the ketophosphonate product was isolated in a stable enolic form.

  DOI：

  10.1021/jo00130a024

文献信息

• Potassium permanganate/carboxylic acid/organic solvent: a powerful reagent for enone oxidation and aryl coupling reactions
  作者：Ayhan S. Demir、Hamide Findik

  DOI：10.1016/j.tet.2008.05.004

  日期：2008.6

  with potassium permanganate and acetic acid, in which acetoxylation products were obtained in 74–96% yields. The same reaction was carried out with carboxylic acids other than acetic acid, which furnished corresponding acyloxy ketones with the same regioselectivity. For the first time, formyloxylation products were synthesized in a 61–85% yield by using formic acid. The potassium permanganate and acetic

  用高锰酸钾和乙酸进行烯酮的α'-乙酰氧基化和芳族酮的α-乙酰氧基化，得到乙酰氧基化产物的产率为74-96％。用乙酸以外的羧酸进行相同的反应，这提供了具有相同区域选择性的相应的酰氧基酮。首次使用甲酸以61-85％的产率合成了甲酰氧基化产物。高锰酸钾和乙酸法也用于芳基偶联反应。苯中的芳基硼酸和芳基肼与高锰酸钾和乙酸的反应反过来提供了85-96％的收率。我们已经证明高锰酸钾/羧酸/有机溶剂的行为像乙酸锰（III）。
• A Pd(II)-Catalyzed Ring-Expansion Reaction of Cyclic 2-Azidoalcohol Derivatives: Synthesis of Azaheterocycles
  作者：Shunsuke Chiba、Yan-Jun Xu、Yi-Feng Wang

  DOI：10.1021/ja9049564

  日期：2009.9.16

  A Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via an unprecedented C-C bond cleavage-C-N bond formation sequence, providing substituted azaheterocycles.

  发现 Pd(II) 催化的环状 2-叠氮醇衍生物的扩环反应通过前所未有的 CC 键断裂-CN 键形成序列进行，提供取代的氮杂杂环。
• Photochemical Approaches to the Bilobalide Core
  作者：Jens Emsermann、Till Opatz

  DOI：10.1002/ejoc.201700461

  日期：2017.6.23

  Bilobalide is a tetracyclic sesquiterpene containing three contiguous γ-lactone rings and an unusual tert-butyl group, which is found in the leaves of the ginkgo tree (Ginkgo biloba). Three different photochemical approaches towards bilobalide's unique skeleton are presented. A meta photocycloaddition, a [2 + 2] photocycloaddition, and a Paternò–Büchi-reaction were chosen as the respective key steps

  白果内酯是含有三个连续γ内酯环和一个不寻常的四环倍半萜叔丁基，其在银杏树（叶发现银杏）。提出了三种不同的光化学方法对白果内酯独特的骨架。甲元光环，[2 + 2]光环，和一个的Paternò-步琪反应被选为相应关键步骤。
• Experiments in steroid synthesis: oestrone
  作者：D. J. Crispin、A. E. Vanstone、J. S. Whitehurst

  DOI：10.1039/j39700000010

  日期：——

  Some work leading to syntheses of oestrone is presented. It was generally found necessary to protect the 1-carbonyl function in 5,6,7,7a-tetrahydro-8β-methylindane-1,5-dione before the introduction of alkyl groups at position 4. Alkylations of 2-methylcyclopentane-1,3-dione have been made and the results compared with similar studies on 2-methylcyclohexane-1,3-dione.

  介绍了一些导致雌酮合成的工作。通常发现在引入4位烷基之前必须保护5,6,7,7a-四氢-8β-甲基茚满-1,5-二酮中的1-羰基官能团。2-甲基环戊烷-1的烷基化，制备了3-二酮，并将结果与​​2-甲基环己烷-1,3-二酮的类似研究进行了比较。
• Synthetic Studies toward Sordarin: Building Blocks for the Terpenoid Core and for Analogues Thereof
  作者：Arnaud Schulé、Huan Liang、Jean-Pierre Vors、Marco A. Ciufolini

  DOI：10.1021/jo801911s

  日期：2009.2.20

  bi- and tricyclic building blocks for the elaboration of sordaricin and its analogues are described. The target molecules were obtained through inter- and intramolecular Diels−Alder reactions of a number of previously unknown cyclopentadienes. Unusual properties of 3-cyanoenones and 1-cyanocyclopentadienes have been unveiled and circumvented.

  描述了用于制造索达霉素及其类似物的双环和三环结构单元的途径。目标分子是通过许多先前未知的环戊二烯的分子间和分子内Diels-Alder反应获得的。3-氰基烯酮和1-氰基环戊二烯的不寻常特性已经被揭开并被规避。