(+)-(E,R_S)-1-(p-tolylsulfinyl)-4-methoxy-3-pentene-2-one | 561276-74-2

• 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: (+)-(E,R_S)-1-(p-tolylsulfinyl)-4-methoxy-3-pentene-2-one
• 英文别名: (E)-4-methoxy-1-[(R)-(4-methylphenyl)sulfinyl]pent-3-en-2-one
• CAS: 561276-74-2
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: IQYGAPSTWJIVAJ-VGMNTSGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-(E,R_S)-1-(p-tolylsulfinyl)-4-methoxy-3-pentene-2-one 在 二异丁基氢化铝 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以81%的产率得到(+)-(E,2R,R_S)-1-(p-tolylsulfinyl)-4-methoxy-3-pentene-2-ol
  参考文献：
  名称：

  New insights into the reduction of β,δ-diketo-sulfoxides

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(03)00125-3
• 作为产物：
  描述：

  (E)-ethyl 3-methoxy-2-butenoate 、 (R)-(+)-甲基对甲苯砜 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以55%的产率得到(+)-(E,R_S)-1-(p-tolylsulfinyl)-4-methoxy-3-pentene-2-one
  参考文献：
  名称：

  New insights into the reduction of β,δ-diketo-sulfoxides

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(03)00125-3

文献信息

• Preparation of enantiomerically pure (E)-β-sulfinylenones from β-ketoesters
  作者：Naïma Khiri、Amandine Lefranc、Guy Solladié、Gilles Hanquet

  DOI：10.1016/j.tetlet.2005.06.151

  日期：2005.8

  Enantiomerically pure (E)-beta-sulfinylenones are smoothly prepared from beta-ketoesters in three steps with good overall yield. Since they can be the substrates of many diastereoselective reactions, they represent versatile precursors of a wide range of chiral building blocks. We propose a rationale to explain the formation of (E)-beta-sulfinylen ones from the corresponding delta-enol-methylethers. (c) 2005 Elsevier Ltd. All rights reserved.