Methyl (2S*,3R*,4R*)-3-hydroxy-2-methyl-4-phenylvalerate | 72691-75-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Methyl (2S*,3R*,4R*)-3-hydroxy-2-methyl-4-phenylvalerate
• 英文别名: methyl 3-hydroxy-2-methyl-4-phenylpentanoate；Methyl (2S^*,3R^*,4R^*)-3-hydroxy-2-methyl-4-phenylvalerate
• CAS: 72691-75-9
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: XTBJNKAQFHJLMY-JFGNBEQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-苯基丙醛 在 sodium methylate 、 锌 作用下， 反应 0.17h， 生成 Methyl (2S*,3R*,4R*)-3-hydroxy-2-methyl-4-phenylvalerate
  参考文献：
  名称：

  A highly stereoselective synthesis of aldols employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes

  摘要：

  DOI：

  10.1016/s0040-4039(00)96931-4

文献信息

• Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensation
  作者：Clayton H. Heathcock、Charles T. Buse、William A. Kleschick、Michael C. Pirrung、John E. Sohn、John Lampe

  DOI：10.1021/jo01294a030

  日期：1980.3
• Highly stereoselective reformatsky reactions of 3-(2-Bromopropionyl)-2-oxazolidone derivatives with various aldehydes
  作者：Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4020(01)87087-3

  日期：1991.1

  The Reformatsky reactions of 3-(2-bromopropionyl)-2-oxazolidone derivatives with various aldehydes were investigated to elucidate the effects of substituents in the 2-oxazolidone moieties on their diastereoselectivities. The highest 2,3-syn-diastereoselectivity (2,3-syn:2,3-anti = 98:2) could be realized at -78-degrees-C by employing sterically crowded 3-(2-bromopropionyl)-4,4-dibutyl-5,5-pentamethylene-2-oxazolidone. While high 2,3-syn-3,4-syn-selectivity (2,3-syn-3,4-syn:2,3-syn-3,4-anti = 94:6) was also accomplished by the reaction with dl-2-phenylpropanal, application of this reaction to enantioselective synthesis of 2,3-syn-aldols was found to be unrewarding. The observed diastereoselectivities could be accounted for by the chelating transition state models.
• Adam, Waldemar; Nestler, Bernd, Liebigs Annalen der Chemie, 1990, # 10, p. 1051 - 1053
  作者：Adam, Waldemar、Nestler, Bernd

  DOI：——

  日期：——