4-hydroxy-4-(4-methoxyphenyl)pentan-2-one | 36238-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-hydroxy-4-(4-methoxyphenyl)pentan-2-one
• 英文别名: 4-Hydroxy-4-(4-methoxyphenyl)pentan-2-one
• CAS: 36238-17-2
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: UPDCRXPRKAQTLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  4-hydroxy-4-(4-methoxyphenyl)pentan-2-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 4-(4-甲氧基-苯基)-戊-3-烯-2-酮
  参考文献：
  名称：

  Catalytic Stereospecific Allyl–Allyl Cross-Coupling of Internal Allyl Electrophiles with AllylB(pin)

  摘要：

  Application of internal electrophiles in catalytic stereospecific allyl allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation can be synthesized with high enantiomeric excess.

  DOI：

  10.1021/ol500456s
• 作为产物：
  描述：

  2-(4-methoxyphenyl)pent-4-en-2-ol 在 chromium(VI) oxide 、 palladium dichloride 作用下， 以 水 、 乙腈 为溶剂， 生成 4-hydroxy-4-(4-methoxyphenyl)pentan-2-one
  参考文献：
  名称：

  痕量OH导向的Wacker氧化消除反应，替代Wittig烯烃/醇醛缩合反应：由均烯丙基醇一锅法合成α，β-不饱和和非共轭酮

  摘要：

  用于一锅合成的新方法β-取代和β，β -二取代的α，β通过顺序的PdCl不饱和的甲基酮从高烯丙基醇2 / CRO 3促进的瓦克法然后酸介导的脱水反应已经开发。值得注意的是，内部均烯丙基醇在相同的方案下可选择性地引入区域选择性的非共轭不饱和羰基化合物。证明了一种新的基于原料的α，β-不饱和和非共轭甲基酮的合成方法。

  DOI：

  10.1021/acs.joc.6b01899

文献信息

• Isopropylmagnesium chloride-promoted unilateral addition of Grignard reagents to β-diketones: one-pot syntheses of β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones
  作者：Rui Yuan、Dan Zhao、Li-Yuan Zhang、Xiang Pan、Yan Yang、Pei Wang、Hong-Feng Li、Chao-Shan Da

  DOI：10.1039/c5ob02072g

  日期：——

  unilateral additions of Grignard reagents to acyclic or cyclic β-diketones were effectively promoted by sub-stoichiometric amounts of i-PrMgCl to afford β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones, respectively. Also, the addition of Grignard reagents to acyclic β-diketones followed by a reaction with cyclic β-diketones in a one-pot process was put forward. The reaction mechanism was discussed

  亚化学计量的i-PrMgCl有效促进了格氏试剂向无环或环状β-二酮的区域选择性单侧添加，从而分别提供了β-叔羟基酮或3-取代的环-2-烯酮。此外，提出了在单锅法中将格氏试剂添加到无环β-二酮中，然后与环状β-二酮反应。通过化学实验，氢-氘交换和质谱对反应机理进行了详细讨论，以解释其高区域选择性。
• Action des organomagnésiens sur les composés β-dicarbonylés V. Synthèses de β-diols bitertiaires à partir de β-hydroxycétones. Induction asymétrique 1-3
  作者：Jacqueline Michel、Perséphone Canonne

  DOI：10.1139/v71-677

  日期：1971.12.15

  Addition of organomagnesium compounds to β-hydroxyketones with an asymmetric center gave a diastereoisomeric mixture of symmetric ditertiary β-diols, the ratio of meso and threo forms depending on the nature of the inductive group.The configurations of the β-diols were determined using their respective n.m.r. spectra in which the methyl and the methylene protons have different chemical shifts.The conformations of the β-hydroxyketones and the β-diols were studied by i.r. spectroscopy. Models for a preferred attack of the organomagnesium compounds are proposed and product-determining transition states for the reactions are also suggested.

  有机镁化合物加到具有不对称中心的β-羟基酮中，形成对映异构体混合物，对称的二叔丁基β-二醇，meso和threo形式的比例取决于电子诱导基团的性质。通过它们各自的n.m.r.谱图确定了β-二醇的构型，其中甲基和亚甲基质子具有不同的化学位移。通过i.r.光谱研究了β-羟基酮和β-二醇的构象。提出了有机镁化合物优先攻击的模型，并推荐了反应的产物确定过渡态。
• Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of <i>α</i>,<i>β</i>-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols
  作者：Venkati Bethi、Rodney A. Fernandes

  DOI：10.1021/acs.joc.6b01899

  日期：2016.9.16

  A new method for one-pot synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols by sequential PdCl2/CrO3-promoted Wacker process followed by an acid-mediated dehydration reaction has been developed. Remarkably, internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol. A new starting material-based

  用于一锅合成的新方法β-取代和β，β -二取代的α，β通过顺序的PdCl不饱和的甲基酮从高烯丙基醇2 / CRO 3促进的瓦克法然后酸介导的脱水反应已经开发。值得注意的是，内部均烯丙基醇在相同的方案下可选择性地引入区域选择性的非共轭不饱和羰基化合物。证明了一种新的基于原料的α，β-不饱和和非共轭甲基酮的合成方法。
• Catalytic Stereospecific Allyl–Allyl Cross-Coupling of Internal Allyl Electrophiles with AllylB(pin)
  作者：Hai Le、Amanda Batten、James P. Morken

  DOI：10.1021/ol500456s

  日期：2014.4.18

  Application of internal electrophiles in catalytic stereospecific allyl allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation can be synthesized with high enantiomeric excess.