1-(Methoxymethoxy)-4-phenyl-2-butanone | 170451-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(Methoxymethoxy)-4-phenyl-2-butanone
• 英文别名: 1-methoxymethoxy-4-phenyl-2-butanone；1-(Methoxymethoxy)-4-phenylbutan-2-one
• CAS: 170451-01-1
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: PSHUGFOYHZASCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Methoxymethoxy)-4-phenyl-2-butanone 在 乙基溴化镁 作用下， 反应 2.33h， 生成 1-Phenyl-3-(propionyloxy)-3-<(methoxymethoxy)methyl>-4-pentene
  参考文献：
  名称：

  A ligand assisted Claisen rearrangement

  摘要：

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes via heteroatom mediated substrate pre-organization prior to rearrangement.

  DOI：

  10.1016/s0040-4039(00)61392-8
• 作为产物：
  描述：

  4-phenyl-2-(trimethylsiloxy)-1-butene 在 四丁基氟化铵 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 1-(Methoxymethoxy)-4-phenyl-2-butanone
  参考文献：
  名称：

  A Chelation-Controlled Ester Enolate Claisen Rearrangement

  摘要：

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.

  DOI：

  10.1021/jo00121a029

文献信息

• Highly Efficient Synthesis of Terminal Alkenes from Ketones
  作者：Hélène Lebel、Danielle Guay、Valérie Paquet、Kim Huard

  DOI：10.1021/ol049085p

  日期：2004.9.1

  [reaction: see text] The rhodium(I)-catalyzed methylenation of ketones using trimethylsilyldiazomethane proceeds to give the corresponding alkenes in good yields (60-97%). The use of an excess of 2-propanol and 1,4-dioxane as a solvent were instrumental to obtain the desired alkenes in high yields. Superior results were achieved with the rhodium(I)-catalyzed methylenation in comparison with the standard

  [反应：见正文]使用三甲基甲硅烷基重氮甲烷进行铑（I）催化的酮的甲基化反应，得到了相应的烯烃，收率很高（60-97％）。使用过量的2-丙醇和1，4-二恶烷作为溶剂有助于以高收率获得所需的烯烃。与标准Wittig反应相比，铑（I）催化的亚甲基化获得了优异的结果。
• A ligand assisted Claisen rearrangement
  作者：Marie E. Krafft、Sandra Jarrett、Olivier A. Dasse

  DOI：10.1016/s0040-4039(00)61392-8

  日期：1993.12

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes via heteroatom mediated substrate pre-organization prior to rearrangement.
• A Chelation-Controlled Ester Enolate Claisen Rearrangement
  作者：Marie E. Krafft、Olivier A. Dasse、Sandra Jarrett、Anne Fievre

  DOI：10.1021/jo00121a029

  日期：1995.8

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.