(E)-4-羟基-1-(4-甲氧基苯基)-4-甲基戊-1-烯-3-酮 | 81791-30-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (E)-4-羟基-1-(4-甲氧基苯基)-4-甲基戊-1-烯-3-酮
• 英文名称: (E)-4-hydroxy-1-(4-methoxyphenyl)-4-methylpent-1-en-3-one
• CAS: 81791-30-2
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: WDUZIWGNQKQNOU-RMKNXTFCSA-N

物化性质

• 沸点：
  374.5±27.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-羟基-1-(4-甲氧基苯基)-4-甲基戊-1-烯-3-酮 以 三氟乙酸 为溶剂， 生成 5-(4-methoxy-phenyl)-2,2-dimethyl-dihydro-furan-3-one
  参考文献：
  名称：

  分子间和分子内迈克尔加成反应之间电子效应的逆转

  摘要：

  在三氟乙酸中测量（E）-2-甲基-3-氧代-3-苯基-5-苯基戊-4-烯-2-醇及其对甲氧基衍生物的环化速率，以及逆反应速率，表示在分子间迈克尔加成中不存在的立体电子起源的影响。

  DOI：

  10.1039/c39820000036
• 作为产物：
  描述：

  5-(4-methoxy-phenyl)-2,2-dimethyl-dihydro-furan-3-one 以 三氟乙酸 为溶剂， 生成 (E)-4-羟基-1-(4-甲氧基苯基)-4-甲基戊-1-烯-3-酮
  参考文献：
  名称：

  分子间和分子内迈克尔加成反应之间电子效应的逆转

  摘要：

  在三氟乙酸中测量（E）-2-甲基-3-氧代-3-苯基-5-苯基戊-4-烯-2-醇及其对甲氧基衍生物的环化速率，以及逆反应速率，表示在分子间迈克尔加成中不存在的立体电子起源的影响。

  DOI：

  10.1039/c39820000036

文献信息

• Palladium-Catalyzed Oxidative Cyclizations:  Synthesis of Dihydropyranones and Furanones
  作者：Maud Reiter、Hazel Turner、Rebecca Mills-Webb、Véronique Gouverneur

  DOI：10.1021/jo051274d

  日期：2005.10.1

  good yields. The Pd(II)-mediated oxidative cyclization was expanded to α-hydroxyenones leading to furan-3(2H)-one derivatives, which include natural product bullatenone and a known precursor of geiparvarin. The sole product of the oxidative cyclization of α,β-dihydroxyenone was a five-membered furan-3(2H)-one derivative, suggesting that the ring closure of these diols is both chemo- and regioselective

  将引起各种β-羟基烯酮的硼介导的顺式和反式立体选择性醛醇缩合反应与Pd （II）介导的氧化环化反应偶联，以高收率得到2,3,6-三取代的顺式和反式二氢吡喃酮。Pd （II）介导的氧化环化反应扩展为α-羟基烯酮，生成了呋喃3（2 H）-one衍生物，其中包括天然产物Bullatenone和已知的geiparvarin前体。α，β-二羟基烯酮的氧化环化的唯一产物是五元呋喃-3（2 H）-one衍生物，这表明这些二醇的闭环具有化学选择性和区域选择性。
• Enantioselective Conjugate Radical Addition to α‘-Hydroxy Enones
  作者：Sunggi Lee、Chae Jo Lim、Sunggak Kim、Rajesh Subramaniam、Jake Zimmerman、Mukund P. Sibi

  DOI：10.1021/ol061634z

  日期：2006.9

  Enantioselective conjugate radical addition to alpha'-hydroxy alpha,beta-unsaturated ketones, compounds containing bidentate donors, has been investigated. It has been found that radical additions to alpha'-hydroxy alpha,beta-unsaturated ketones in the presence of Mg(NTf2)2 and bisoxazoline ligand 5a proceeded cleanly, yielding the addition products in high chemical yields and good enantiomeric excesses

  已研究了向α'-羟基α，β-不饱和酮（含双齿供体的化合物）的对映选择性共轭基团的加成反应。已经发现，在Mg（NTf2）2和双恶唑啉配体5a存在下，向α′-羟基α，β-不饱和酮的自由基加成反应干净进行，以高化学产率和良好的对映体过量产生加成产物。
• Lewis acid mediated elimination and rearrangement reactions of α-chlorosulfides derived from phenylthio-substituted 4,5-dihydrofuran-3(2H )-ones.
  作者：Daniel G. McCarthy、Cornelius C. Collins、Joan P. O’Driscoll、Simon E. Lawrence

  DOI：10.1039/a905169d

  日期：——

  Phenylthio-substituted 4,5-dihydrofuran-3(2H)-ones were converted into α-chlorosulfides in a highly diastereoselective manner with sulfuryl chloride. Treatment of the chlorides with stoichiometric amounts of Lewis acids gave furan-3(2H)-one products resulting from elimination and aryl group migrations. Similar behaviour was observed with an α-acetoxy sulfide derivative. The X-ray crystal structures of a representative α-chlorosulfide and of a novel, ring sulfenylated product were determined.

  用硫酰氯将苯硫基取代的 4,5-二氢呋喃-3(2H)-酮高度非对映选择性地转化为δ-氯硫化物。用等量的路易斯酸处理这些氯化物后，呋喃-3(2H)-酮产物会发生消除和芳基迁移。δ-乙酰氧基硫化物衍生物也有类似的表现。研究人员还测定了一种具有代表性的δ-氯硫化物和一种新型环亚磺化产物的 X 射线晶体结构。
• Chiang, Pei-Chen; Rommel, Michael; Bode, Jeffrey W., Journal of the American Chemical Society, 2009, vol. 131, p. 8714 - 8718
  作者：Chiang, Pei-Chen、Rommel, Michael、Bode, Jeffrey W.

  DOI：——

  日期：——
• α‘-Hydroxy Enones as Achiral Templates for Lewis Acid-Catalyzed Enantioselective Diels−Alder Reactions
  作者：Claudio Palomo、Mikel Oiarbide、Jesús M. García、Alberto González、Elena Arceo

  DOI：10.1021/ja0368002

  日期：2003.11.1

  alpha'-Hydroxy enones react with dienes in the presence of (S,S)-[Cu(tBu-box)](OTf)2 or (S,S)-[Cu(tBu-box)](SbF6)2 (2 to 10 mol %) to afford the corresponding Diels-Alder adducts in high yield and selectivity. Isomeric ratios (regioselectivity, endo/exo or cis/trans) of up to >99:1 and ee values of up to >99% are obtained. Significantly, difficult dienes such as isoprene, 2,3-dimethyl butadiene and piperylene behave satisfactorily. Subsequent oxidative cleavage of the ketol in the resulting cycloadducts by treatment with cerium ammonium nitrate (CAN) yields the corresponding enantiopure carboxylic acids. Alternatively, carbonyl addition and subsequent diol cleavage with CAN produces the corresponding ketone adducts.