methyl (5S)-3-oxo-5-phenyl-5-trimethylsilyloxypentanoate | 292038-16-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl (5S)-3-oxo-5-phenyl-5-trimethylsilyloxypentanoate
• CAS: 292038-16-5
• 化学式: C₁₅H₂₂O₄Si
• 分子量: 294.423
• InChiKey: RGJJGNDLIKXXAC-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5S)-3-oxo-5-phenyl-5-trimethylsilyloxypentanoate 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 (5S) methyl δ-hydroxy-δ-phenyl-β-oxo-pentanoate
  参考文献：
  名称：

  Enantioselective aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene promoted by chiral Ti(IV)/BINOL complex

  摘要：

  Enantiomerically enriched delta-hydroxy-beta-ketoesters are easily available by aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene in the presence of Ti(O-iPr)(4)/(S)-(-)-BINOL system. All reaction mixtures were separated by column chromatography and mostly isolated in moderate to good yields and all in high enantiomeric excesses. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00200-7
• 作为产物：
  描述：

  Chan's diene 、 苯甲醛 在 titanium(IV) isopropylate 、 S-1,1'-联-2-萘酚 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以19%的产率得到methyl (5S)-3-oxo-5-phenyl-5-trimethylsilyloxypentanoate
  参考文献：
  名称：

  Enantioselective aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene promoted by chiral Ti(IV)/BINOL complex

  摘要：

  Enantiomerically enriched delta-hydroxy-beta-ketoesters are easily available by aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene in the presence of Ti(O-iPr)(4)/(S)-(-)-BINOL system. All reaction mixtures were separated by column chromatography and mostly isolated in moderate to good yields and all in high enantiomeric excesses. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00200-7

文献信息

• A new procedure for the enantioselective vinylogous aldol reaction of Chan’s diene
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tetasy.2006.12.016

  日期：2006.12

  Chiral delta-hydroxy-delta-ketoesters are easily available through the enantio selective vinylogous aldol reaction of Chan's diene promoted by a SiCl4/chiral phosphoramide catalytic system. The procedure is conveniently exploited for a very rapid approach to (+)-kavain, a natural bio-active alpha-pyrone compound. (c) 2007 Elsevier Ltd. All rights reserved.
• Enantioselective aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene promoted by chiral Ti(IV)/BINOL complex
  作者：Annunziata Soriente、Margherita De Rosa、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/s0957-4166(00)00200-7

  日期：2000.6

  Enantiomerically enriched delta-hydroxy-beta-ketoesters are easily available by aldol condensation of 1,3-bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene in the presence of Ti(O-iPr)(4)/(S)-(-)-BINOL system. All reaction mixtures were separated by column chromatography and mostly isolated in moderate to good yields and all in high enantiomeric excesses. (C) 2000 Elsevier Science Ltd. All rights reserved.