2-methyl-3-phenylsulfanyl-cyclopent-2-enone | 82909-44-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methyl-3-phenylsulfanyl-cyclopent-2-enone
• 英文别名: 2-Methyl-3-phenylsulfanylcyclopent-2-en-1-one
• CAS: 82909-44-2
• 化学式: C₁₂H₁₂OS
• 分子量: 204.293
• InChiKey: FZFIMAPNDWNGAS-UHFFFAOYSA-N

物化性质

• 沸点：
  325.6±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-phenylsulfanyl-cyclopent-2-enone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 133.0h， 生成 1-(phenylthio)-2-methylcyclopentene
  参考文献：
  名称：

  Matoba, Katsuhide; Tokizawa, Minoru; Morita, Takashi, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 1, p. 368 - 372

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-1,3-环戊二酮 在 sodium hydroxide 、 三溴化磷 作用下， 以 氯仿 、 水 为溶剂， 反应 24.0h， 生成 2-methyl-3-phenylsulfanyl-cyclopent-2-enone
  参考文献：
  名称：

  Matoba, Katsuhide; Tokizawa, Minoru; Morita, Takashi, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 1, p. 368 - 372

  摘要：

  DOI：

文献信息

• Reaction of β-halo α, β-unsaturated ketones with cuprate reagents. Efficient syntheses of β, β-dialkyl ketones and β-alkyl α,β-unsaturated ketones. A synthesis of (<i>Z</i>)-jasmone
  作者：Edward Piers、Kin Fai Cheng、Isao Nagakura

  DOI：10.1139/v82-185

  日期：1982.5.15

  Treatment of the 3-halo-2-cyclohexen-1-ones 11–15 and 17 with an excess of lithium dimethylcuprate provided good to excellent yields of the corresponding 3,3-dimethylcyclohexanones 21–24. Similar reactions involving the β-bromo cyclopentenones 19 and 20 stopped at the monoaddition stage, producing the cyclopentenones 40 and 43. Reaction of the β-bromo cyclohexenones 12 and 15 with 1.1 equiv. of lithium dimethylcuprate did not effect clean conversion of these substrates into the corresponding 3-methyl-2-cyclohexen-1-ones. When a series of β-bromo enones 12, 14–19 were allowed to react with the lithium (phenylthio)(alkyl)cuprates 44–47, the corresponding β-alkyl enones were, in general, produced cleanly and efficiently. However, reaction of 3-bromo-2-methyl-2-cyclopenten-1-one (19) with the cuprate reagent 44 gave mainly the β-phenylthio enone 49. This undesired result could be avoided by employing, in the place of 19, the β-iodo cyclopentenone 50, which reacted smoothly with 44 to give a high yield of 2,3-dimefhyl-2-cyclopenten-1-one (40). Reaction of 3-bromo-2-cyclohexen-1-one (14) with 3 equiv. of the mixed vinylcuprate reagent 48 gave 3-(3-butenyl)-2-cyclohexen-1-one (32). Alkylation of 1,3-cyclopentanedione with (Z)-1-chloro-2-pentene afforded compound 51, which was converted into the β-bromo enone 52. Treatment of the latter substance with lithium dimethylcuprate provided (Z)-jasmone (53).

  将3-卤代-2-环己烯-1-酮11-15和17与过量的二甲基溴化锂处理，得到相应的3,3-二甲基环己酮21-24，收率良好至优良。涉及β-溴代环戊烯酮19和20的类似反应在单加成阶段停止，产生环戊烯酮40和43。β-溴代环己烯酮12和15与1.1当量的二甲基溴化锂反应未对这些底物进行干净转化为相应的3-甲基-2-环己烯-1-酮产生影响。当一系列β-溴代烯酮12、14-19与苯基硫代烷基铜盐44-47反应时，通常产生相应的β-烷基烯酮，而且效率高。然而，3-溴代-2-甲基-2-环戊烯-1-酮（19）与铜盐试剂44反应主要产生β-苯基硫代烯酮49。通过使用β-碘代环戊烯酮50代替19，可以避免这种不良结果，后者与44反应顺利，产生高收率的2,3-二甲基-2-环戊烯-1-酮（40）。3-溴代-2-环己烯-1-酮（14）与混合乙烯铜盐试剂48的3当量反应产生3-(3-丁烯基)-2-环己烯-1-酮（32）。1,3-环戊二酮与(Z)-1-氯-2-戊烯烷基化生成化合物51，进一步转化为β-溴代烯酮52。后一物质经二甲基溴化锂处理得到(Z)-茉莉酮（53）。
• Moenomycin a: New chemistry that allows to attach the antibiotic to reporter groups, solid supports, and proteins
  作者：Uwe Kempin、Lothar Hennig、Dietmar Knoll、Peter Welzel、Dietrich Müller、Astrid Markus、Jean van Heijenoort

  DOI：10.1016/s0040-4020(97)10234-4

  日期：1997.12

  Moenomycin A (18) on reaction with the diazonium salt derived from bifunctional (protected) 15 yields the coupling product 19 which on reduction is converted into the moenomycin thiol derivative 21. Thiol 21 has been used to prepare selectively moenomycin dansyl and biotin adducts 26 and 28, respectively. This work was performed with the aim to use moenomycin as a tool for studies of the transglycosylation

  Moenomycin A（18）与衍生自双功能（受保护的）15的重氮盐反应生成偶联产物19，偶联产物19还原后转化为Moenomycin硫醇衍生物21。硫醇21已分别用于选择性地制备新霉素丹磺酰基和生物素加合物26和28。进行这项工作的目的是使用莫能霉素作为研究肽聚糖生物合成中转糖基化步骤的工具。
• Stereocontrolled cyclopentenone synthesis via cycloaddition
  作者：Barry M. Trost、Peter Seoane、Serge Mignani、Murat Acemoglu

  DOI：10.1021/ja00201a032

  日期：1989.9
• Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd-Catalyzed Decarboxylation of Enol Carbonate and β-Ketoester Substrates
  作者：Barry M. Trost、Robert N. Bream、Jiayi Xu

  DOI：10.1002/anie.200504421

  日期：2006.5.5
• Matoba, Katsuhide; Morita, Takashi; Yamazaki, Takao, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 7, p. 3001 - 3005
  作者：Matoba, Katsuhide、Morita, Takashi、Yamazaki, Takao

  DOI：——

  日期：——