ethyl (5S)-5-hydroxy-6-[(R)-(4-methylphenyl)sulfinyl]-3-oxohexanoate | 141423-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (5S)-5-hydroxy-6-[(R)-(4-methylphenyl)sulfinyl]-3-oxohexanoate
• CAS: 141423-14-5
• 化学式: C₁₅H₂₀O₅S
• 分子量: 312.387
• InChiKey: DXXLLKOJHBSCRM-YEJXKQKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-己烯酸,3-羟基-6-[(4-甲基苯基)亚硫酰基]-5-羰基-,乙基酯,(R)- 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以80%的产率得到ethyl (5S)-5-hydroxy-6-[(R)-(4-methylphenyl)sulfinyl]-3-oxohexanoate
  参考文献：
  名称：

  Asymmetric Synthesis of β-Hydroxyketones, Precursors of Chiral 1,3-Diols, from β, δ-Diketosulfoxides.

  摘要：

  (R) beta, delta-diketosulfoxides were reduced with DIBAL to (S2R(S)) delta-keto beta-hydroxysulfoxides (de > 98%) which can be easily transformed into syn or anti chiral 1,3-diols by known procedures.

  DOI：

  10.1016/s0040-4039(00)91685-x

文献信息

• New insights into the reduction of β,δ-diketo-sulfoxides
  作者：Gilles Hanquet、Xavier J. Salom-Roig、Laurence Gressot-Kempf、Steve Lanners、Guy Solladié

  DOI：10.1016/s0957-4166(03)00125-3

  日期：2003.5

  New developments in the reduction of beta,delta-diketo-sulfoxides, a reaction that affords important key intermediates for total synthesis, are described. We showed without ambiguity using NMR experiments, that the beta-carbonyl group is totally enolised. This result is inconsistent with the previous hypothesis, which supposed the other tautomer (enolisation at the delta-position) as the major one. We propose a rationale to explain the side reactions occurring during the reduction of unprotected beta,delta-diketo-sulfoxides and showed that judicious protection of the delta-carbonyl group gave all diastereoisomers of beta-hydroxy-delta-ketosulfoxides. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Asymmetric Synthesis of β-Hydroxyketones, Precursors of Chiral 1,3-Diols, from β, δ-Diketosulfoxides.
  作者：Guy Solladié、Nasser Ghiatou

  DOI：10.1016/s0040-4039(00)91685-x

  日期：1992.3

  (R) beta, delta-diketosulfoxides were reduced with DIBAL to (S2R(S)) delta-keto beta-hydroxysulfoxides (de > 98%) which can be easily transformed into syn or anti chiral 1,3-diols by known procedures.