2-甲氧基-3-甲基环戊-2-烯-1-酮 | 14189-85-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲氧基-3-甲基环戊-2-烯-1-酮
• 英文名称: 2-methoxy-3-methylcyclopent-2-en-1-one
• 英文别名: NSC-177460；2-methoxy-3-methyl-2-cyclopenten-1-one；2-Methoxy-3-methyl-2-cyclopenten-1-on；2-methoxy-3-methylcyclopent-2-enone；2-methoxy-3-methylcyclopentenone；2-methoxy-3-methyl-cyclopent-2-enone；2-Cyclopenten-1-one, 2-methoxy-3-methyl-
• CAS: 14189-85-6
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: GTEGQQAMGYNDKS-UHFFFAOYSA-N

物化性质

• 沸点：
  45-47 °C(Press: 0.4 Torr)
• 密度：
  1.03±0.1 g/cm3(Predicted)
• LogP：
  0.091 (est)

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：
  0.57
• 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：

  2-甲氧基-3-甲基环戊-2-烯-1-酮 生成 甲基环戊烯醇酮
  参考文献：
  名称：

  天然和非天然前列腺素的手性经济全合成

  摘要：

  AbstractUsing a meso‐compound which is asymmetrically substituted with a chiral moiety as an intermediate, prostaglandins have been synthesized. Since the undesired enantiomer is readily recycled, this approach leads to a synthesis with high chiral efficiency. In addition it is possible to prepare both enantiomeric configurations of prostaglandins by simply altering the sequence of reactions. This concept should be generally useful in the synthesis of optically active molecules.

  DOI：

  10.1002/hlca.19750580228
• 作为产物：
  描述：

  1-Methoxy-2,5-hexandion 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以56%的产率得到2-甲氧基-3-甲基环戊-2-烯-1-酮
  参考文献：
  名称：

  Stetter, Hermann; Mohrmann, Karl-Heinrich; Schlenker, Walter, Chemische Berichte, 1981, vol. 114, # 2, p. 581 - 596

  摘要：

  DOI：

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）。
• Highly Enantioselective Approach to Geminal Bisphosphonates by Organocatalyzed Michael-Type Addition of β-Ketoesters
  作者：Marinella Capuzzi、Dario Perdicchia、Karl Anker Jørgensen

  DOI：10.1002/chem.200701317

  日期：2008.1

  developed for the asymmetric synthesis of bisphosphonate derivatives, a class of pharmaceutically important molecules. Cheap and commercially available dihydroquinine effectively catalyzed conjugate additions of cyclic beta-ketoesters to ethylidenebisphosphonate esters, leading to optically active geminal bisphosphonates, bearing an all-carbon substituted quaternary stereocenter, in high yields and

  已经开发了一种有价值的有机催化方案，用于一类重要药物双膦酸酯衍生物的不对称合成。廉价且可商购的二氢奎宁可有效催化环状β-酮酸酯与亚乙基双膦酸酯的共轭加成反应，从而形成光学活性双膦双膦酸酯，具有全碳取代的季立体中心，且收率高，对映选择性高达ee的99％。还成功地完成了迈克尔加合物对相应的双膦酸或乙烯基膦酸酯的进一步精制，同时保持了光学纯度。
• Cooperative benzylic–oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds
  作者：Nitin S. Dange、Jacob R. Stepherson、Caitlan E. Ayala、Frank R. Fronczek、Rendy Kartika

  DOI：10.1039/c5sc01914a

  日期：——

  Herein we describe a direct capture of benzylic–oxyallylic stabilized carbocations with high value nucleophiles towards regioselective construction of α-quaternary centers.

  在这里，我们描述了对苄基-氧基烯丙基稳定的碳阳离子进行直接捕获，利用高价值亲核试剂实现α-夸特位中心的区域选择性构建。
• Spiroketals via oxidative rearrangement of enol ethers
  作者：David L. Waller、Corey R. J. Stephenson、Peter Wipf

  DOI：10.1039/b612992g

  日期：——

  Oxidative rearrangement of cyclic enol ethers leads to alpha-alkoxyesters. In the presence of a neighboring spiroether, this approach provides a stereoselective access to spiroketals. A modified proposal for the biosynthesis of acutumine is presented.

  环状烯醇醚的氧化重排产生α-烷氧基酯。在存在相邻的螺醚的情况下，该方法提供了对螺环酮的立体选择通道。提出了修改后的方案，用于合成金盏花。
• Acetoacetic acid ester derivatives for the manufacture of
  申请人：Givaudan Corporation

  公开号：US04892966A1

  公开（公告）日：1990-01-09

  The invention is concerned with a novel process for the manufacture of compounds of the formula ##STR1## wherein R.sup.1 signifies C.sub.1-5 -alkyl, especially methyl, ethyl, propyl or isopropyl, and the radicals R.sup.2 each independently represent hydrogen or C.sub.1-5 -alkyl, especially hydrogen or methyl, ethyl, propyl or isopropyl. The process is characterized in that a compound of the formula ##STR2## wherein R stands for C.sub.1-4 -alkoxy, chlorine, bromine or C.sub.1-4 -alkanoyloxy, R.sup.1 and R.sup.2 have the above significance and R.sup.3 represents C.sub.1-4 -alkyl. is hydrolyzed and subjected to an aldol condensation and, where R=C.sub.1-4 -alkoxy, the reaction product is subsequently subjected to an acid treatment. The compounds I are for the most part known flavoring substances.

  这项发明涉及一种用于制备以下化合物的新型工艺：其中R.sup.1表示C.sub.1-5-烷基，特别是甲基、乙基、丙基或异丙基，基团R.sup.2分别独立地代表氢或C.sub.1-5-烷基，特别是氢或甲基、乙基、丙基或异丙基。该工艺的特点在于，化合物的公式为：其中R代表C.sub.1-4-烷氧基、氯、溴或C.sub.1-4-烷酰氧基，R.sup.1和R.sup.2具有上述含义，R.sup.3代表C.sub.1-4-烷基。经水解和醛缩反应处理化合物后，其中R=C.sub.1-4-烷氧基时，反应产物随后经酸处理。这些化合物I大多数是已知的调味物质。