3-叔丁基-2-甲基-2-环戊烯-1-酮 | 33958-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-叔丁基-2-甲基-2-环戊烯-1-酮
• 英文名称: 3-tert-butyl-2-methyl-2-cyclopenten-1-one
• 英文别名: 3-tert-butyl-2-methyl-2-cyclopentenone；3-tert-butyl-2-methylcyclopent-2-enone；2-Methyl-3-tert.-butyl-2-cyclopenten-1-on；3-tert-Butyl-2-methylcyclopent-2-en-1-on；2-Methyl-3-t-butyl-2-cyclopropenon；3-tert-butyl-2-methylcyclopent-2-en-1-one
• CAS: 33958-65-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: FFFSXTZEQAFWGM-UHFFFAOYSA-N

物化性质

• 沸点：
  218.2±10.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3-叔丁基-2-甲基-2-环戊烯-1-酮 在 lithium aluminium tetrahydride 作用下， 生成 3-tert-Butyl-2-methylcyclopent-2-en-1-ol
  参考文献：
  名称：

  Preparation and reactions of cyclopropylallyl cations

  摘要：

  DOI：

  10.1021/ja00746a023
• 作为产物：
  描述：

  2,3-epoxy-3-methylcyclopentanone 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.25h， 生成 3-叔丁基-2-甲基-2-环戊烯-1-酮
  参考文献：
  名称：

  Reaction of cyclic .alpha.-hydroxy epoxides with a strong base: a new 1,2-rearrangement, evidence for a carbenoid pathway.

  摘要：

  Several substituted five- and six-membered cyclic alpha,beta-unsaturated ketones are readily available by treatment of the corresponding alpha-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1,2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.

  DOI：

  10.1021/ja00156a006

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）。
• Antczak, Kazimierz; Kingston, John F.; Alward, Sandra J., Canadian Journal of Chemistry, 1984, vol. 62, p. 829 - 837
  作者：Antczak, Kazimierz、Kingston, John F.、Alward, Sandra J.、Fallis, Alex G.

  DOI：——

  日期：——
• Reaction of cyclic .alpha.-hydroxy epoxides with a strong base: a new 1,2-rearrangement, evidence for a carbenoid pathway.
  作者：Eric Doris、Luc Dechoux、Charles Mioskowski

  DOI：10.1021/ja00156a006

  日期：1995.12

  Several substituted five- and six-membered cyclic alpha,beta-unsaturated ketones are readily available by treatment of the corresponding alpha-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1,2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.
• Preparation and reactions of cyclopropylallyl cations
  作者：T. S. Sorensen、K. Rajeswari

  DOI：10.1021/ja00746a023

  日期：1971.8