2-[(Z)-丁-2-烯基]-4-羟基-3-甲基-环戊-2-烯-1-酮 | 17190-74-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-[(Z)-丁-2-烯基]-4-羟基-3-甲基-环戊-2-烯-1-酮
• 英文名称: (+-)-cis-Cinerolon
• 英文别名: cinerolone；cinerolon；(+/-)-(Z)-Cinerolon；2-[(Z)-but-2-enyl]-4-hydroxy-3-methylcyclopent-2-en-1-one
• CAS: 17190-74-8
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: YLKLJBPHNWWPSF-ARJAWSKDSA-N

物化性质

• 沸点：
  102-105 °C(Press: 0.05 Torr)
• 密度：
  1.067±0.06 g/cm3(Predicted)
• 保留指数：
  1641

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  2-[(Z)-丁-2-烯基]-4-羟基-3-甲基-环戊-2-烯-1-酮 、 (1S-顺式)-2,2-二甲基-3-(2-甲基丙-1-烯基)环丙烷甲酰氯 生成 (+/-)(1Ξ)-cis-chrysanthemumic acid-((Ξ)-3-but-2c-enyl-2-methyl-4-oxo-cyclopent-2-enyl ester)
  参考文献：
  名称：

  Part-list cuing in amnesic patients: Evidence for a retrieval deficit

  摘要：

  Part-list cuing-the detrimental effect of the presentation of a subset of learned items on recall of the remaining items-was examined in amnesic patients and healthy control subjects. Subjects studied two types of categorized item lists: lists in which each category consisted of strong and moderate items and lists in which each category consisted of weak and moderate items. The subjects recalled a category's strong and weak items in either the presence of or absence of the moderate items serving as retrieval cues. In healthy subjects, part-list cuing impaired recall of the strong items but not of the weak items; in amnesics, part-list cuing impaired recall of both types of items. Part-list cuing is often attributed to a change in the retrieval process from a more effective one when cues are. absent to a less effective one when they are present. On the basis of this view, our results indicate that part-list cuing causes a stronger retrieval inefficiency in amnesic patients than in healthy people.

  DOI：

  10.3758/bf03195772
• 作为产物：
  描述：

  (S)-2-but-2c-enyl-4-hydroxy-3-methyl-cyclopent-2-enone semicarbazone 在 potassium hydrogensulfate 、 乙醚 作用下， 生成 2-[(Z)-丁-2-烯基]-4-羟基-3-甲基-环戊-2-烯-1-酮
  参考文献：
  名称：

  CONSTITUENTS OF PYRETHRUM FLOWERS. XVII. THE ISOLATION OF FIVE PYRETHROLONE SEMICARBAZONES

  摘要：

  DOI：

  10.1021/jo01178a003

文献信息

• Synthesis of ketols of the natural pyrethrins
  作者：L. Crombie、P. Hemesley、Gerald Pattenden

  DOI：10.1039/j39690001016

  日期：——

  A stereospecific five-stage synthesis of (±)-cis-pyrethrolone is described, involving cis-octa-1,3-dien-7-one as the key intermediate. The ethylene acetal of this ketone was made by a Wittig reaction, under salt-free condiditions, with vaporised acraldehyde. The overall yield for the synthesis was 21%, and it provides highly pure (pm;)-cis-pyrethrolone for the first time. The material is spectrally

  描述了（±）-顺式-吡咯烷酮的立体有择的五阶段合成，涉及顺式-octa-1,3-dien-7-one作为关键中间体。该酮的乙缩醛是通过Wittig反应在无盐条件下与汽化的丙烯醛反应制得的。合成的总产率为21％，并且它首次提供了高纯度的（pm；）-顺式-吡咯烷酮。该物质与自然（+）-吡咯烷酮样品在光谱上相同。
• Photochemistry of 2-(prop-2-enyl)cyclopent-2-enones
  作者：Michael J. Bullivant、Gerald Pattenden

  DOI：10.1039/p19760000249

  日期：——

  or OAc), (6a), and (21) undergo di-π-methane rearrangement to vinylcyclopropanes [(3a and b), (7), and (29), respectively], whereas the side-chain substituted analogues (2b; R = OMe or OAc), (2c; R = OAc), and (6b), under similar conditions, undergo Z–E isomerisation. Sensitisation and quenching experiments with (2a; R = OAc) suggest that (3) is derived from a triplet excited state of (2a). The reactivity

  已经研究了几种取代的2-（丙-2-烯基）环戊-2-烯酮的光化学。2-（丙-2-烯基）环戊-2-烯酮（2a; R = OMe或OAc），（6a）和（21）进行二-π-甲烷重排为乙烯基环丙烷[[3a和b），（ 7）和（29）]，而侧链取代的类似物（2b; R = OMe或OAc），（2c; R = OAc）和（6b）在相似条件下进行Z – E异构化。用（2a; R = OAc）进行的敏化和淬灭实验表明（3）源自（2a）的三重激发态。在（2a），（6a）和（21）以及（2b），（2c）和（6b）之间的反应性差异是基于在（分子的侧链。
• Optically active 4-hydroxy-2-cyclopentenones, and their production
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0115860A2

  公开（公告）日：1984-08-15

  A process for preparing an optically active 4-hydroxy-2- cylopentenone of the formula: wnerem R1 is a nyarogen atom or a methyl group, R2 is an alkyl group, an alkenyl group or an alkynyl group and the asterisk (*) indicates an asymmetric configuration, which comprises subjecting an optically active 4-cylopentenone-alcohol of the formula: wherein R1 and R2 are each as defined above, the asterisk (*) indicates an asymmetric configuration and the substituents R1 and R2 take a cis-configuration to rearrangement while maintainig the original steric configuration.

  一种制备具有光学活性的 4-羟基-2-环戊烯酮的工艺，其式如下： 其中 R1 是炔原子或甲基，R2 是烷基、烯基或炔基，星号（*）表示不对称构型，该工艺包括将具有光学活性的 4-环戊烯酮醇进行重排，其式如下： 其中 R1 和 R2 各自如上定义，星号（*）表示不对称构型，取代基 R1 和 R2 采用顺式构型，同时保持原有的立体构型。
• Crombie et al., Journal of the Chemical Society, 1951, p. 2445,2448
  作者：Crombie et al.

  DOI：——

  日期：——
• Constituents of Pyrethrum Flowers. XXIV. Synthetic dl-cis-Cinerolone and Other Cyclopentenolones^1,2
  作者：Milton S. Schechter、Nathan Green、F. B. LaForge

  DOI：10.1021/ja01139a050

  日期：1952.10

表征谱图