2-Propargyl-2-cyclopentenon | 60033-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Propargyl-2-cyclopentenon
• 英文别名: 2-(Prop-2-yn-1-yl)cyclopent-2-en-1-one；2-prop-2-ynylcyclopent-2-en-1-one
• CAS: 60033-26-3
• 化学式: C₈H₈O
• 分子量: 120.151
• InChiKey: PLBAGYQZYBEBJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Propargyl-2-cyclopentenon 在 palladium on activated charcoal 氢气 、 nickel diacetate 作用下， 以 乙醇 为溶剂， 生成 2-allyl-2-cyclopenten-1-one
  参考文献：
  名称：

  Pirillo,D. et al., Farmaco, Edizione Scientifica, 1978, vol. 33, p. 156 - 158

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(prop-2-yn-1-yl)cyclohexane-1,3-dione 生成 2-Propargyl-2-cyclopentenon
  参考文献：
  名称：

  Traverso; Pirillo, Farmaco, Edizione Scientifica, 1976, vol. 31, # 4, p. 305 - 307

  摘要：

  DOI：

文献信息

• Tunable Cyclization Strategy for the Synthesis of Zizaene-, <i>allo</i>-Cedrane-, <i>seco</i>-Kaurane-, and <i>seco</i>-Atesane-Type Skeletons
  作者：Qianqian Yang、Wenjing Ma、Gaopeng Wang、Wenli Bao、Xiaoshu Dong、Xuefeng Liang、Lizhi Zhu、Chi-Sing Lee

  DOI：10.1021/acs.orglett.7b02610

  日期：2017.10.6

  A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels–Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne–enolates through Lewis acid dependent 5-

  一种多功能路易斯酸介导的环化策略已经被开发用于选择性地建立zizaene-，同种异体-cedrane-，开环-kaurane-，和开环-atesane型骨架。的zizaene-和开环-atesane型骨架可以以级联的方式，它涉及与二甲硅烷氧基二烯和carbocyclization炔烯醇化物的通过路易斯酸依赖性5-或6-环烯酮的Diels-Alder反应来获得外切挖模式。这种环化策略也被用于tashironin的核心合成。
• Process for producing disubstituted 4-hydroxycyclopentenones; monosubstituted cyclopentendiones and 4-hydroxycyclopentenones
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0022162A1

  公开（公告）日：1981-01-14

  A method of producing a 4-hydroxycyclopentenone rep resented by the formula, wherein R, is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atom, which comprises reacting a furylcarbinol compound of the formula, wherein R, is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, wherein R is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula. wherein R, is as defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula, R2MgX wherein R2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, wherein R1 and R2 are as defined above; and reacting the cyclopentenone compound in the presence of a base. The 4-hydroxycyclopentenones are useful intermediates of agricultural chemicals.

  一种生产4-羟基环戊烯酮的方法，其式如下 其中 R 为烷基、烯基、炔基、环烷基、噻吩基、苯基、对甲基苄基或苄基，R2 为具有 6 个或更少碳原子的烷基、烯基或炔基，该方法包括使式、 其中 R 如上定义，在酸存在下，在水和有机溶剂的混合溶剂中反应，得到式中的环戊烯酮化合物、 其中 R 如上定义； 在氧化剂存在下，使环戊烯酮化合物反应，得到式......的环戊二酮化合物。 其中 R 如上定义； 将环戊烯二酮化合物与式中的格氏试剂反应、 R2MgX 其中 R2 如上定义，X 为氯、溴或碘原子，与式中的格氏试剂反应，得到式中的氧代环戊烯化合物、 其中 R1 和 R2 如上定义；以及 在碱存在下使环戊烯酮化合物反应。 4- 羟基环戊烯酮是有用的农药中间体。
• Process for preparing optically active 4-hydroxy-2-cyclipentenones
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0153653A1

  公开（公告）日：1985-09-04

  A process for preparing an optically active 2-substituted or unsubstituted-4-hydroxy-2-cyclopentenone of the formula. wherein R is a hydrogen atom, an allyl group or a propargyl group, which comprises reacting the corresponding 2- substituted or unsubstituted-4-hydroxy-2-cyclopentenone of the formula: wherein R is defined above with a lactone chosen from (1R,5S)-6,6-Edimethyl-4-hydroxy-3-oxabicycto(3.1.0]hexan-2- one or (1S,5R)-6,6-dimethyl-4-hydroxy-3-oxabicyclo[3.1.0]-hexan-2-one in a molar ratio of 1.5 - 2 : 1 in the presence of p-toluenesulfonic acid or benzenesulfonic acid in the coexistence of an organic solvent under elimination of water as an azeotropic mixture with the organic solvent to obtain a reaction mixture comprising (1R,5S)-6,6-dimethyl-3-oxa-4(R)-[1(R)-4-oxo-2-substituted or unsubstituted-2-cyclo- pentenyloxy]bicyclo[3.1.0]hexan-2-one or (1S,5R)-6,6-dimethyl-3-oxa-4(S)-[1(S)-4-oxo-2-substituted or unsubstituted-2-cyclopentenyloxy]bicyclo[3.1.0]hexan-2-one of the formula: wherein R is as defined above, of which either one isomer is contained in a considerably larger amount than the other isomer, separating the isomer having the larger content from the reaction mixture and hydrolyzing the separated isomer to give the optically active 2-substituted or unsubstituted-4-hydroxy-2-cyclopentenone.

  一种制备具有光学活性的式 2-取代或未取代-4-羟基-2-环戊烯酮的工艺。 其中 R 为氢原子、烯丙基或丙炔基，该工艺包括将相应的式 2-取代或未取代-4-羟基-2-环戊烯酮与选自(1R,5S)、(1R,5S)和(1R,5S)的内酯反应： 其中 R 如上定义，与选自 (1R,5S)-6,6-二甲基-4-羟基-3-氧杂双环[3.1.0]己烷-2-酮或 (1S,5R)-6,6-二甲基-4-羟基-3-氧杂双环[3.1.0]己烷-2-酮的内酯在摩尔比为 1.5 - 2 : 1 的对甲苯磺酸或苯磺酸存在下，在有机溶剂的共沸混合物中消除水，得到包含 (1R,5S)-6,6-二甲基-3-氧杂-4(R)-[1(R)-4-氧代-2-取代或未取代-2-环戊烯氧基]双环[3.1.0]己-2-酮或式(1S,5R)-6,6-二甲基-3-氧杂-4(S)-[1(S)-4-氧代-2-取代或未取代-2-环戊烯氧基]双环[3.1.0]己-2-酮： 其中 R 如上文所定义，其中一种异构体的含量大大高于另一种异构体，从反应混合物中分离出含量较高的异构体，水解分离出的异构体，得到光学活性的 2-取代或未取代-4-羟基-2-环戊烯酮。
• PIRILLO D.; TRAVERSO G.; RESCIA G., FARMACO ED. SCI., 1978, 33, NO 2, 156-158
  作者：PIRILLO D.、 TRAVERSO G.、 RESCIA G.

  DOI：——

  日期：——
• TORII S.; TANAKA H.; KUDAI T.; WATANABE S., CHEM. LETT., 1979, NO 2, 147-150
  作者：TORII S.、 TANAKA H.、 KUDAI T.、 WATANABE S.

  DOI：——

  日期：——