3-羟基-2-(3-甲基丁-2-烯基)环己-2-烯酮 | 926656-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-2-(3-甲基丁-2-烯基)环己-2-烯酮
• 英文名称: 3-hydroxy-2-(3-methylbut-2-enyl)cyclohex-2-enone
• 英文别名: 3-Hydroxy-2-(3-methylbut-2-enyl)cyclohex-2-en-1-one
• CAS: 926656-88-4
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: YPEJKTCUWQBALF-UHFFFAOYSA-N

物化性质

• 沸点：
  292.6±40.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-羟基-2-(3-甲基丁-2-烯基)环己-2-烯酮 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 65.5h， 生成 3-methyl-2,4-bis(3-methyl-but-2-enyl)cyclohex-2-enone
  参考文献：
  名称：

  2，6-异戊烯基取代的环己酮衍生物与丙二酰氯的α，α'环化：应用于短时间合成（+/-）-clusianone。生物遗传样中间体的形成和重排。

  摘要：

  为成功地将3,3-二甲基-2,4,6-三甲苯基环己酮甲硅烷基烯醇醚与丙二酰氯的Effenbergerα，α'环化找到条件，得到了35％的相应双环[3.3.1]壬烷三酮产率，该结果允许短合成（+/-）-clusianone。还以25％的收率分离了异构体重排的双环[3.3.1]壬烷-三酮，改变路易斯酸导致以38％的收率形成了经黄酮基取代的间苯三酚衍生物。这两种最后产物的形成机制模拟了PPAP的生物遗传途径。[反应：请参见文字]。

  DOI：

  10.1021/ol062736s
• 作为产物：
  描述：

  1,3-环己二酮 、 1-溴-3-甲基-2-丁烯 在 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 以70%的产率得到3-羟基-2-(3-甲基丁-2-烯基)环己-2-烯酮
  参考文献：
  名称：

  2，6-异戊烯基取代的环己酮衍生物与丙二酰氯的α，α'环化：应用于短时间合成（+/-）-clusianone。生物遗传样中间体的形成和重排。

  摘要：

  为成功地将3,3-二甲基-2,4,6-三甲苯基环己酮甲硅烷基烯醇醚与丙二酰氯的Effenbergerα，α'环化找到条件，得到了35％的相应双环[3.3.1]壬烷三酮产率，该结果允许短合成（+/-）-clusianone。还以25％的收率分离了异构体重排的双环[3.3.1]壬烷-三酮，改变路易斯酸导致以38％的收率形成了经黄酮基取代的间苯三酚衍生物。这两种最后产物的形成机制模拟了PPAP的生物遗传途径。[反应：请参见文字]。

  DOI：

  10.1021/ol062736s

文献信息

• Protecting group free syntheses of (±)-columbianetin and (±)-angelmarin
  作者：Eric B.J. Harris、Martin G. Banwell、Anthony C. Willis

  DOI：10.1016/j.tetlet.2011.10.036

  日期：2011.12

  A five-step and protecting group free synthesis of (±)-columbianetin from cyclohexane-1,3-dione is reported. The former compound was converted into its p-hydroxycinnamate derivative, (±)-angelmarin, using Coster’s esterification procedure. Efforts to modify the synthesis so as to prepare angelmarin and columbianetin in an enantioselective manner are described.

  据报道由环己烷-1,3-二酮五步无保护基合成（±）-钴胺素。使用Coster的酯化方法，将前一种化合物转化为其对羟基肉桂酸酯衍生物（±）-Angelmarin。描述了修饰合成以努力以对映选择性的方式制备安吉林和香豆素的努力。
• Domino Aryne Annulation via a Nucleophilic–Ene Process
  作者：Hai Xu、Jia He、Jiarong Shi、Liang Tan、Dachuan Qiu、Xiaohua Luo、Yang Li

  DOI：10.1021/jacs.8b01005

  日期：2018.3.14

  1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.
• New chemical access for pyran core embedded derivatives from bisalkenylated 1,3-diketones and 1,3-diketoesters via tandem C-dealkenylation and cyclization
  作者：T. Narender、S. Sarkar、K. Venkateswarlu、J.K. Kumar

  DOI：10.1016/j.tetlet.2010.10.030

  日期：2010.12

  New chemical access has been developed for the synthesis of pyran core embedded derivatives from 1,3-diketones and 1,3-diketoesters, in which the active methylene group of 1,3-diketone or 1,3-diketoester was alkenylated with three equivalents of alkenyl bromides in presence NaH to give bisalkenyl 1,3-diketones or 1,3-diketoesters and the resultant bisalkenyl 1,3-diketones or 1,3-diketoesters were reacted with AlCl3 at room temperature to furnish pyran core embedded derivatives in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantioselective Wacker-Type Cyclization of 2-Alkenyl-1,3-diketones Promoted by Pd-SPRIX Catalyst
  作者：Kazuhiro Takenaka、Suman C. Mohanta、Mahesh L. Patil、C. V. Laxman Rao、Shinobu Takizawa、Takeyuki Suzuki、Hiroaki Sasai

  DOI：10.1021/ol1013069

  日期：2010.8.6

  An enantioselective intramolecular Wacker-type cyclization of 2-alkenyl-1,3-diketones catalyzed by a Pd(II)-SPRIX complex was developed. The reaction proceeded in a 6-endo-trig mode to give the desired chromene derivatives with moderate to good enantioselectivity. Isomerization of C-C double bonds via a pi-allyl Pd intermediate was involved as the key step.
• Direct palladium/carboxylic acid-catalyzed C-allylation of cyclic 1,3-diones with allylic alcohols in water
  作者：Kim-Hong Gan、Ciou-Jyu Jhong、Shyh-Chyun Yang

  DOI：10.1016/j.tet.2007.11.082

  日期：2008.2

  The direct activation of C-O bonds in allylic alcohols in water as a suspension medium by palladium complexes has been accelerated by carrying out the reactions in the presence of a carboxylic acid. The palladium-catalyzed allylation of cyclic 1,3-diones using allylic alcohols directly gave the corresponding C-allylated products in good yields. (c) 2007 Elsevier Ltd. All rights reserved.