2-hydroxymethyl-3-methyl-1-phenyl-1-butanone | 63481-29-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxymethyl-3-methyl-1-phenyl-1-butanone
• 英文别名: 2-(Hydroxymethyl)-3-methyl-1-phenylbutan-1-one；2-(hydroxymethyl)-3-methyl-1-phenylbutan-1-one
• CAS: 63481-29-8
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: OZJCZHAHRCKGRE-UHFFFAOYSA-N

物化性质

• 沸点：
  316.7±25.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 苯甲醇 在 hydridochlorotris(triphenylphosphine)ruthenium(II) 、 苯甲醛 作用下， 以 苯 为溶剂， 反应 2.0h， 以45%的产率得到2-hydroxymethyl-3-methyl-1-phenyl-1-butanone
  参考文献：
  名称：

  氢化钌催化α，β-不饱和醛与伯醇的交叉偶联反应合成2-羟基甲基酮

  摘要：

  使用RuHCl（CO）（PPh 3）3作为催化剂，可以实现α，β-不饱和醛与伯醇的交叉偶联反应，生成2-羟甲基酮。这种原子经济反应很可能是通过α，β-不饱和醛的加氢钌化反应进行的，然后是烯醇与醛的醛醇缩合反应，生成α-甲酰化的酮，然后与伯醇进行转移氢化反应，生成α-羟甲基酮。 。还原步骤可产生醛，参与下一催化循环。

  DOI：

  10.1021/ol902289r

文献信息

• Lanthanide Trifluoromethanesulfonates as Stable Lewis Acids in Aqueous Media. Yb(OTf)₃Catalyzed Hydroxymethylation Reaction of Silyl Enol Ethers with Commercial Formaldehyde Solution
  作者：Shu Kobayashi

  DOI：10.1246/cl.1991.2187

  日期：1991.12

  Silyl enol ethers smoothly react with commercial formaldehyde solution to give the corresponding hydroxymethylated adducts in high yields by the promotion of a catalytic amount of ytterbium(III) triflate (Yb(OTf)3), which is a stable Lewis acid in aqueous media. Other lanthanide triflates are also found to be effective.

  通过催化量的三氟甲磺酸镱 (III) (Yb(OTf)3)（一种在水性介质中是稳定的路易斯酸），甲硅烷基烯醇醚与商业甲醛溶液顺利反应，以高产率得到相应的羟甲基化加合物。其他镧系元素三氟甲磺酸盐也被发现是有效的。
• Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media
  作者：Shu Kobayashi、Iwao Hachiya

  DOI：10.1021/jo00092a017

  日期：1994.7

  Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)(3)), were found to be stable Lewis acids in water. In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde solution) was activated and the hydroxymethylation reaction of silyl enol ethers proceeded smoothly. Lanthanide triflates were also quite effective in the aldol reaction of silyl enol ethers with aldehydes in aqueous media, and water-soluble aldehydes such as acetaldehyde, acrolein, and chloroacetaldehyde could be employed for direct use. Moreover, in all these reactions, lanthanide triflates were quantitatively recovered after the reactions were completed and could be reused.
• Kobayashi; Hashiya; Ishitani, Russian Journal of Organic Chemistry, 1996, vol. 32, # 2, p. 193 - 202
  作者：Kobayashi、Hashiya、Ishitani、Moriwaki、Nagayama

  DOI：——

  日期：——
• Synthesis of 2-Hydroxymethyl Ketones by Ruthenium Hydride-Catalyzed Cross-Coupling Reaction of α,β-Unsaturated Aldehydes with Primary Alcohols
  作者：Aurélien Denichoux、Takahide Fukuyama、Takashi Doi、Jiro Horiguchi、Ilhyong Ryu

  DOI：10.1021/ol902289r

  日期：2010.1.1

  The cross-coupling reaction of α,β-unsaturated aldehydes with primary alcohols to give 2-hydroxymethyl ketones was achieved using RuHCl(CO)(PPh3)3 as a catalyst. This atom-economical reaction is likely to proceed via the hydroruthenation of α,β-unsaturated aldehydes followed by an aldol reaction of the resultant enolates with aldehydes to give α-formylated ketones, which undergo transfer hydrogenation

  使用RuHCl（CO）（PPh 3）3作为催化剂，可以实现α，β-不饱和醛与伯醇的交叉偶联反应，生成2-羟甲基酮。这种原子经济反应很可能是通过α，β-不饱和醛的加氢钌化反应进行的，然后是烯醇与醛的醛醇缩合反应，生成α-甲酰化的酮，然后与伯醇进行转移氢化反应，生成α-羟甲基酮。 。还原步骤可产生醛，参与下一催化循环。