3-methoxy-2,5-dimethyl-2-cyclopenten-1-one | 51036-27-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯酯类
• 英文名称: 3-methoxy-2,5-dimethyl-2-cyclopenten-1-one
• 英文别名: 2,5-Dimethyl-3-methoxy-2-cyclopentenon；2-Cyclopenten-1-one, 3-methoxy-2,5-dimethyl-；3-methoxy-2,5-dimethylcyclopent-2-en-1-one
• CAS: 51036-27-2
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: HJPIFXGUIDSRAP-UHFFFAOYSA-N

物化性质

• 沸点：
  230.3±29.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-2,5-dimethyl-2-cyclopenten-1-one 在 palladium on activated charcoal sodium chlorite 、 sodium dihydrogenphosphate 、 cerium(III) chloride 、 2-甲基-2-丁烯 、 伯吉斯试剂 、 碘代三甲硅烷 、 氢气 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 六甲基二硅氮烷 、 lithium diisopropyl amide 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 丙酮 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 33.05h， 生成 (1R*,4S*,6S*,9S*)-6-isopropyl-2,9-dimethyl-3-(trifluoromethanesulfonyl)tricyclo[4.3.0.0^4,9]non-2-ene
  参考文献：
  名称：

  Synthesis of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas

  摘要：

  A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug (Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00735-3
• 作为产物：
  描述：

  3-methoxy-2-methylcyclopent-2-enone 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.5h， 以76%的产率得到3-methoxy-2,5-dimethyl-2-cyclopenten-1-one
  参考文献：
  名称：

  Synthesis of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas

  摘要：

  A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug (Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00735-3

文献信息

• Diastereoselective double michael additions of vinylogous esters and thexyldimethylsilyl triflate-induced cyclizations
  作者：Dieter Schinzer、Markus Kalesse

  DOI：10.1016/s0040-4039(00)92283-4

  日期：1991.1

  Double Michael additions of vinylogous esters of type 1 with crotyl ester generates diastereoselectively bicyclo[2.2.2]octanone 2 with four defined chiral centers via a synclinal transition state. Thexyldimethylsilyl enol ethers of type 5 and 10 undergo smooth cyclization to bicyclo[3.3.1]nonenones 7 and bicylo[3.3.0]octenones 12 by addition of Lewis acids.

  类型1的乙烯基酯与巴豆酸酯的双Michael加成反应生成非对映体选择性的双环[2.2.2]辛酮2，该化合物通过邻向过渡态具有四个定义的手性中心。通过添加路易斯酸，使类型5和10的二甲基二甲基甲硅烷基烯醇醚顺利环化为双环[3.3.1]壬烯酮7和双环[3.3.0]辛烯酮12。
• Silica gel-catalyzed cyclizations of mixed ketene acetals
  作者：Dieter Schinzer、Markus Kalesse、Jazid Kabbara

  DOI：10.1016/s0040-4039(00)80726-1

  日期：1988.1

  Mixed ketene acetals of type undergo smooth cyclization upon treatment with silica gel yielding diastereoselectively bicyclo[2.2.2]octanones of type . Alternatively, the same result was obtained by exposure of the substrates to TiCl4 at low temperature.

  在用硅胶处理后，混合型烯酮缩醛会发生平滑环化反应，生成非对映选择性双环[2.2.2]辛酮。可替代地，通过在低温下将基板暴露于TiCl 4来获得相同的结果。
• Synthesis of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas
  作者：Shigefumi Kuwahara、Shiharu Hamade、Walter Soares Leal、Jiro Ishikawa、Osamu Kodama

  DOI：10.1016/s0040-4020(00)00735-3

  日期：2000.10

  A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug (Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure. (C) 2000 Elsevier Science Ltd. All rights reserved.