4-acetoxy-cyclopentenone | 61740-24-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-acetoxy-cyclopentenone
• 英文别名: 4-Acetoxy-2-cyclopenten-1-on；4-oxocyclopent-2-en-1-yl acetate；(4-oxocyclopent-2-en-1-yl) acetate
• CAS: 61740-24-7
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: YNCKAQVPQJWLJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetoxy-cyclopentenone 在 氢氧化钾 、 硫酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 11.0h， 生成 cis-4-oxocyclopentane-1,2-diacetic acid bis(methyl ester)
  参考文献：
  名称：

  Harre, Michael; Winterfeldt, Ekkehard, Chemische Berichte, 1982, vol. 115, # 4, p. 1437 - 1447

  摘要：

  DOI：
• 作为产物：
  描述：

  4-环戊烯-1,3-二酮 在 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 反应 5.08h， 生成 4-acetoxy-cyclopentenone
  参考文献：
  名称：

  An Efficient Synthesis of 4(S)-Hydroxycyclopent-2-enone

  摘要：

  An efficient synthesis of 4(S)-hydroxycyclopent-2-enone of high optical purity, a key synthon used in natural product synthesis, is described. The method is suitable for large-scale synthesis.

  DOI：

  10.1021/jo00128a029

文献信息

• Synthesis of 2-heterosubstituted cyclopent-2-en-1-ones: a preliminary study of the strategic design of antiviral compounds
  作者：Karzan Khaleel Hameed、Ahmed Anwar Dezaye、Faiq Hamasaid Hussain、Teresa Basile、Misal Giuseppe Memeo、Paolo Quadrellic

  DOI：10.24820/ark.5550190.p010.672

  日期：——

  heterosubstituted cyclopent-2-en-1-ones through a robust protocol that leads to single 2-substituted compounds is reported. In view of a strategic design of antiviral compounds, the methodology was applied to substituted benzoimidazoles as neutral heterocyclic systems, as models for preliminary evaluation of their antiviral activities. By virtue of NMR investigations the synthetized compounds were structurally

  杂取代的 cyclopent-2-en-1-ones 的合成方法通过一个强大的协议, 导致单个 2-取代化合物。鉴于抗病毒化合物的战略设计，该方法应用于取代苯并咪唑作为中性杂环系统，作为初步评估其抗病毒活性的模型。通过 NMR 研究，合成的化合物在结构上完全确定，构象也从 DFT 计算中确定。初步的生物学测试显示，大多数产品普遍无活性，并预测出一些带有特定取代基的产品。结果表明可能的结构变化容易触发相关的生物活性，以在新化合物中实现它们。
• 4-Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation
  作者：Daniele Mantione、Olatz Olaizola Aizpuru、Misal Giuseppe Memeo、Bruna Bovio、Paolo Quadrelli

  DOI：10.1002/ejoc.201501406

  日期：2016.2

  in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases. The protocol is based on a typical nucleophilic substitution process. Uracil, thymine, 6-chloropurine, and some adenines gave the expected 4-heterosubstituted products along with the isomeric 2-heterosubstituted compounds as minor components. Samples of selected products were evaluated for their antiviral activity in

  外消旋的 4-oxocyclopent-2-en-1-yl 乙酸盐用于短时间合成带有嘧啶和嘌呤杂碱基的核苷类似物。该协议基于典型的亲核取代过程。尿嘧啶、胸腺嘧啶、6-氯嘌呤和一些腺嘌呤产生预期的 4-杂取代产物以及作为次要组分的异构 2-杂取代化合物。在针对属于不同类别的各种病毒的初步筛选中，对选定产品的样品的抗病毒活性进行了评估。发现其中一种化合物对人乳头瘤病毒 (HPV) 具有高度活性。
• [EN] SUBSTITUTED ADENINES AND THE USE THEREOF<br/>[FR] ADENINES SUBSTITUEES ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2006040558A1

  公开（公告）日：2006-04-20

  This invention relates to compounds of Formula (I): and their use in the treatment of bacterial infections.

  这项发明涉及式(I)的化合物及其在治疗细菌感染中的应用。
• Cyclic ketones, their preparation and their use in the synthesis of amino acids
  申请人：——

  公开号：US20030187296A1

  公开（公告）日：2003-10-02

  A method is provided for making an enantiomerically pure of the formula: in which R and R′ represent C1?C10 alkyl, C2?C10 alkenyl or C3?C10 cycloalkyl and the wedges signify (S)- or (R)-stereochemistry, the substituents in compound (II) being trans. Conjugate addition is carried out between an organometallic nucleophile that provides a group R as defined above and (R)-4-acetoxycyclopent-2-en-1-one, (S)-4-acetoxycyclopent-2-en-1-one or a similar compound in which acetoxy is replaced by another leaving group to give, e.g. in the case of the acetoxy compound, a trans 3,4-disubstituted addition product of formula III or IV; The acetyl group is eliminated from the addition product to give an (R)- or (S)-4-alkyl or 4-alkenyl cyclopent-2-en-1-one the compound of formula is then to be hydrogenated to give a cyclopentanone of formula (I) or conjugate addition of a second organometallic nucleophile that provides a group R′ as defined above to the compound of the above formula may be carried out to give a trans 3,4-disubstituted addition product of formula (II). One of the above compounds may be converted e.g. via an intermediate (XV)-(XVIII) (in which the substituents R and R′ and the wedges have the meanings indicated above) to a gabapentin analogue of one of the formulae shown below: in which the substituents R and R′ and the wedges also have the meanings indicated above. 1 2

  提供一种制备公式的对映纯物质的方法：其中R和R′代表C1-C10烷基、C2-C10烯基或C3-C10环烷基，楔形符号表示(S)-或(R)-立体化学，化合物(II)中的取代基为反式。在有机金属亲核试剂和(R)-4-乙酰氧基环戊-2-烯-1-酮、(S)-4-乙酰氧基环戊-2-烯-1-酮或类似化合物之间进行共轭加成，其中乙酰氧基被另一个离去基取代，例如在乙酰氧基化合物的情况下，得到公式III或IV的反式3,4-二取代加成产物；从加成产物中消除乙酰基，得到(R)-或(S)-4-烷基或4-烯基环戊-2-烯-1-酮，然后将该化合物氢化，得到公式(I)的环戊酮，或者对上述公式的化合物进行第二次有机金属亲核试剂的共轭加成，得到公式(II)的反式3,4-二取代加成产物。上述化合物之一可以通过中间体(XV)-(XVIII)（其中取代基R和R′以及楔形符号具有上述所示的含义）转化为下面所示的公式之一的加巴喷丁类似物：其中取代基R和R′以及楔形符号也具有上述所示的含义。
• High Pressure Diels-Alder Reactions of 2-Vinyl-3,4-Dihydronaphthalene. Synthesis of Cyclopenta[c]- and Indeno[c]Phenanthrenones.
  作者：Lucio Minuti、Aldo Taticchi、Eszter Gacs-Baitz、Assunta Marrocchi

  DOI：10.1016/0040-4020(95)00504-2

  日期：1995.8

  A new shorter synthesis of 2-vinyl-3,4-dihydro-naphthalene has been described. The Diels-Alder reactions of this diene with 4-acetoxy-2-cyclopenten-1-one, 3-bromoindan-1-one and inden-1-one under high pressure conditions are reported. A two step synthesis of cyclopenta[c]-and indeno[c]phenanthrenones is discussed. Structure analysis by 1H and 13C NMR spectroscopy is presented.

  已经描述了2-乙烯基-3，4-二氢萘的新的更短的合成。据报道，该二烯在高压条件下与4-乙酰氧基-2-环戊烯-1-酮，3-溴茚满-1-酮和茚满-1-酮的狄尔斯-阿尔德反应。讨论了环戊[c]-和茚并[c]菲咯酮的两步合成。介绍了通过1 H和13 C NMR光谱进行的结构分析。