5-(R)-p-methoxyphenyl-3-oxo-5-(trimethylsilyloxy)-pentanoic acid methyl ester | 356793-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(R)-p-methoxyphenyl-3-oxo-5-(trimethylsilyloxy)-pentanoic acid methyl ester
• 英文别名: methyl (5R)-5-(4-methoxyphenyl)-3-oxo-5-trimethylsilyloxypentanoate
• CAS: 356793-31-2
• 化学式: C₁₆H₂₄O₅Si
• 分子量: 324.449
• InChiKey: OSDIQGCOVXXEOQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(R)-p-methoxyphenyl-3-oxo-5-(trimethylsilyloxy)-pentanoic acid methyl ester 在 三氟乙酸 作用下， 生成 (3R) methyl δ-hydroxy-δ-(p-methoxylphenyl)-β-oxo-pentanoate
  参考文献：
  名称：

  A new procedure for the enantioselective vinylogous aldol reaction of Chan’s diene

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2006.12.016
• 作为产物：
  描述：

  Chan's diene 、 4-甲氧基苯甲醛 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol molecular sieve 作用下， 以 四氢呋喃 为溶剂， 生成 5-(R)-p-methoxyphenyl-3-oxo-5-(trimethylsilyloxy)-pentanoic acid methyl ester
  参考文献：
  名称：

  An efficient asymmetric aldol reaction of Chan's diene promoted by chiral Ti(IV)–BINOL complex

  摘要：

  1.3-Bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene (Chan's diene) can be conveniently used in asymmetric aldol reaction with aromatic, heteroaromatic, alpha,beta -unsaturated and aliphatic aldehydes in the presence of catalytic amounts (2-8% mol) of chiral Ti(IV)/(R)-BINOL complex. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00150-1

文献信息

• 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.