(2S)-hydroxy-3-(phenylthio)propanoic acid | 83023-80-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2S)-hydroxy-3-(phenylthio)propanoic acid
• 英文别名: Propanoic acid, 2-hydroxy-3-(phenylthio)-, (S)-；(2S)-2-hydroxy-3-phenylsulfanylpropanoic acid
• CAS: 83023-80-7
• 化学式: C₉H₁₀O₃S
• 分子量: 198.243
• InChiKey: ZODAXYLLKGRJLD-MRVPVSSYSA-N

物化性质

• 沸点：
  392.0±32.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-hydroxy-3-(phenylthio)propanoic acid 在 吡啶 、 乙酰氯 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methoxycarbonyl-2-phenylsulfanyl-ethyl ester
  参考文献：
  名称：

  Laboratory-scale enzymic/chemical syntheses of D- and L-.beta.-chlorolactic acid and D- and L-potassium glycidate

  摘要：

  DOI：

  10.1021/ja00380a021
• 作为产物：
  描述：

  benzyl (2S)-hydroxy-3-(phenylthio)propionate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以94%的产率得到(2S)-hydroxy-3-(phenylthio)propanoic acid
  参考文献：
  名称：

  Enantioselective synthesis of 2-alkyl-5-methylene-1,3-dioxolan-4-ones and exo-selective Diels-Alder reactions with cyclopentadiene

  摘要：

  Highly stereoselective syntheses of chiral dienophiles (R)-1 and (R)-2 are described. Diazotization of L-serine in the presence of HCI and then treatment of the resulting beta-hydroxy-alpha-chloropropionic acid (S)-7 with KOH provides potassium glycidate ((R)-8) in good yield and high enantiomeric purity. Treatment of (R)-8 with PhSH in MeOH then provides alpha-hydroxy acid (S)-10 that can be purified by recrystallization. Condensation of (S)-10 with either pivalaldehyde or cyclohexanecarboxaldehyde followed by oxidation to the sulfone and DBU-promoted elimination of benzenesulfinic acid then provides dienophiles (R)-1 and (R)-2, respectively. Highly exo-selective Diels-Alder reactions of (R)-1 and (R)-2 with cyclopentadiene are also described. The major cycloadduct (-)-15 (94% of total) from the Diels-Alder reaction of 1 was shown to have an enantiomeric purity of greater-than-or-equal-to 99% ee. This figure defines the lower limit of enantiomeric purity of (R)-1. The diastereofacial selectivity of the Diels-Alder reactions of 1 in the exo manifold (50:1) is greater than that of 2 (20:1), as would be expected on the basis of the different steric requirements of the tert-butyl and cyclohexyl substituents of the two reagents. Consequently, dienophile 1 is the preferred reagent for complex synthetic applications, either as a chiral ketene equivalent or in contexts in which the a-hydroxy acid functionality will be preserved in the ultimate synthetic target. Finally, the possible role of dipole effects on the exo selectivity of the Diels-Alder reactions of these and related dienophiles are briefly discussed.

  DOI：

  10.1021/jo00038a028

文献信息

• An intramolecular Diels-Alder approach to the spirotetronic acid subunits of the quartromicins
  作者：William R. Roush、David A. Barda

  DOI：10.1016/s0040-4039(97)10415-4

  日期：1997.12

  Three of the four diastereomeric spirotetronates (2, 19 and 24) corresponding to the quartromicins were synthesized by a sequence featuring the intramolecular Diels-Alder reaction of 3. An olefin isomerization pathway accounts for formation of the second most abundant cycloadduct, 16. (C) 1997 Elsevier Science Ltd.