(1R,2S,3R)-1-isopropyl-3-hydroxy-2-methylpentyl isopropylcarboxylate | 182073-20-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3R)-1-isopropyl-3-hydroxy-2-methylpentyl isopropylcarboxylate
• 英文别名: [(3R,4S,5R)-5-hydroxy-2,4-dimethylheptan-3-yl] 2-methylpropanoate
• CAS: 182073-20-7
• 化学式: C₁₃H₂₆O₃
• 分子量: 230.348
• InChiKey: WDCSYGZAOLLBMT-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异丁醛 、 5-hydroxy-4,6-dimethyl-3-heptanone 在 titanium(IV) tetrabutoxide 、 R-BINOL 、 辛可宁 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1R,2S,3R)-1-isopropyl-3-hydroxy-2-methylpentyl isopropylcarboxylate 、 rac-(1R,2S,3R)-1-isopropyl-3-hydroxy-2-methylpentyl isopropylcarboxylate 、 (1R,2R,3R)-1-isopropyl-3-hydroxy-2-methylpentyl isopropylcarboxylate 、 (1R,2R,3R)-1-isopropyl-3-hydroxy-2-methylpentyl isopropylcarboxylate
  参考文献：
  名称：

  Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads

  摘要：

  Asymmetric aldol-Tishchenko, reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBU)(2)/Cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.

  DOI：

  10.1021/jo9003635

文献信息

• Toward Asymmetric Aldol-Tishchenko Reactions with Enolizable Aldehydes: Access to Defined Configured Stereotriads, Tetrads, and Stereopentads
  作者：Kerstin Rohr、Robert Herre、Rainer Mahrwald

  DOI：10.1021/jo9003635

  日期：2009.5.15

  Asymmetric aldol-Tishchenko, reactions of enolizable aldehydes and ketones in the presence of chiral BINOLTi(OtBU)(2)/Cinchona alkaloids complexes are described. Different configurative outcomes of these reactions depend on an equilibration through a retro aldol/aldol sequence and can be influenced by the configurative architecture of substrates. The results are explained by means of transition state models and rate constants. These considerations offer a fine-tuning of diastereoselectivity in aldol-Tishchenko reactions. Extensions of this research give access to defined configured stereotriads, stereotetrads, and stereopentads.