(2RS,3SR)-3-hydroxy-3-(pyridin-2-yl)-2-methyl-1-phenylpropan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2RS,3SR)-3-hydroxy-3-(pyridin-2-yl)-2-methyl-1-phenylpropan-1-one
• 英文别名: 3-hydroxy-2-methyl-1-phenyl-3-(pyridin-2-yl)propan-1-one；(2S,3R)-3-hydroxy-2-methyl-1-phenyl-3-pyridin-2-ylpropan-1-one
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: BHXNDOUULLDMJT-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-2-甲醛 、 1-苯基-2-丙烯-1-醇 在 (C5Ph5)Ru(Cl)(CO)2 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 (2RS,3SR)-3-hydroxy-3-(pyridin-2-yl)-2-methyl-1-phenylpropan-1-one 、 (2SR,3SR)-3-hydroxy-3-(pyridin-2-yl)-2-methyl-1-phenylpropan-1-one
  参考文献：
  名称：

  Ru(η5-C5Ph5)(CO)2Cl催化烯丙醇合成β-羟基和β-氨基酮

  摘要：

  描述了一种由 Ru(5-C5Ph5)(CO)2Cl 催化的烯丙醇合成 β-羟基和 β-氨基酮的有效方法。立体电子特性的影响...

  DOI：

  10.1002/ejic.201101014

文献信息

• Repeated Use of the Catalyst in Ln(OTf)₃-Catalyzed Aldol and Allylation Reactions
  作者：Shu Kobayashi、Iwao Hachiya、Yoshinori Yamanoi

  DOI：10.1246/bcsj.67.2342

  日期：1994.8

  triflate)-catalyzed aldol reactions of silyl enol ethers with aldehydes and allylation reactions of tetraallyltin with aldehydes proceeded smoothly in a water–ethanol–toluene system. The reactions proceeded much faster in the above solvent than in water–tetrahydrofuran. Repeated use of the catalyst in these reactions was realized by a very simple procedure.

  镧系元素三氟甲磺酸盐（镧系元素三氟甲磺酸盐）催化的甲硅烷基烯醇醚与醛的羟醛反应以及四烯丙基锡与醛的烯丙基化反应在水-乙醇-甲苯体系中顺利进行。反应在上述溶剂中进行得比在水-四氢呋喃中快得多。在这些反应中重复使用催化剂是通过一个非常简单的程序实现的。
• Ammonium Phenoxides-catalyzed syn-Selective Aldol Reaction Between an Aldehyde and an Trimethylsilyl Enolate
  作者：Hidehiko Fujisawa、Yuzo Nagata、Yoshinori Sato、Teruaki Mukaiyama

  DOI：10.1246/cl.2005.842

  日期：2005.6

  Aldol reactions between aldehydes and trimethylsilyl enolate; generated from ketones or thioesters proceeded smoothly in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide or p-methoxyphenoxide in THF to afford the corresponding aldols in high yields with high syn-selectivity.

  醛与三甲基甲硅烷基烯醇酯之间的羟醛反应；在路易斯碱催化剂如四丁基苯酚铵或对甲氧基苯酚在 THF 中的存在下，由酮或硫酯生成的反应顺利进行，以高产率和高顺式选择性提供相应的羟醛。
• Scandium trisdodecylsulfate (STDS). A new type of lewis acid that forms stable dispersion systems with organic substrates in water and accelerates aldol reactions much faster in water than in organic solvents
  作者：Shū Kobayashi、Takeshi Wakabayashi

  DOI：10.1016/s0040-4039(98)01081-8

  日期：1998.7

  A new type of Lewis acid, scandium trisdodecylsulfate (STDS), was prepared. In the presence of a catalytic amount of STDS, aldol reactions of silyl enol ethers with aldehydes proceeded smoothly in water without using any organic solvents. It was proven that stable dispersion systems including the catalyst and organic substrates were formed in water and that catalytic activity in water was much higher

  制备了一种新型的路易斯酸，三十二烷基硫酸scan（STDS）。在催化量的STDS的存在下，在不使用任何有机溶剂的情况下，甲硅烷基烯醇醚与醛的醛醇缩合反应在水中顺利进行。事实证明，在水中形成了稳定的分散体系，包括催化剂和有机底物，在水中的催化活性远高于在有机溶剂中的催化活性。据我们所知，这是路易斯酸在水中稳定分散体系中催化的第一个例子。
• Iron(II) and Zinc(II) Complexes with Designed <i>pybox</i> Ligand for Asymmetric Aqueous Mukaiyama-Aldol Reactions
  作者：Joanna Jankowska、Joanna Paradowska、Bartosz Rakiel、Jacek Mlynarski

  DOI：10.1021/jo0621470

  日期：2007.3.1

  An iron(II) complex with a hindered hydroxyethyl-pybox (hepybox) ligand shows improved catalytic activity and enantioselectivity for asymmetric Mukaiyama-aldol reactions in aqueous media. This water-stable chiral Lewis acid promotes condensation of aromatic silyl enol ethers with a range of aldehydes with good yields, excellent syn-diastereoselectivity and up to 92% ee. The combination of the same ligand with Zn-II salt is also demonstrated as a remarkably efficient and water-compatible chiral Lewis acid.
• Synthesis of β‐Hydroxy and β‐Amino Ketones from Allylic Alcohols Catalyzed by Ru(η ⁵ ‐C ₅ Ph ₅ )(CO) ₂ Cl
  作者：Agnieszka Bartoszewicz、Martina M. Jeżowska、Kévin Laymand、Juri Möbus、Belén Martín‐Matute

  DOI：10.1002/ejic.201101014

  日期：2012.3

  An efficient method for the synthesis of beta-hydroxy and beta-amino ketones from allylic alcohols catalyzed by Ru(5-C5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of ...

  描述了一种由 Ru(5-C5Ph5)(CO)2Cl 催化的烯丙醇合成 β-羟基和 β-氨基酮的有效方法。立体电子特性的影响...