methyl 5-methoxy-3-oxo-5-phenylpentanoate | 53857-00-4

• 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: methyl 5-methoxy-3-oxo-5-phenylpentanoate
• 英文别名: Methyl 5-methoxy-3-oxo-5-phenylpentanoate
• CAS: 53857-00-4
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: AXMJPFSVSZIEHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 碘 、 三氟乙酸 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.02h， 以82%的产率得到methyl 5-methoxy-3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine

  摘要：

  The synthesis of multifunctionalized beta-ketoesters has been achieved by using molecular iodine as a catalyst under very mild conditions. The vinylogous addition of Chan's diene 1 to carbonyl and carbonyl-related compounds (aldehydes, ketones, imines and acetals) occurred with high efficiencies and with complete gamma-selectivity, giving a useful method for the synthesis of interesting libraries of different delta-functionalized beta-ketoesters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.036

文献信息

• A CONVENIENT METHOD FOR THE SYNTHESIS OF δ-ALKOXY-β-KETOESTER THE TITANIUM TETRACHLORIDE-ACTIVATED REACTION OF DIKETENE WITH ACETAL
  作者：Toshio Izawa、Teruaki Mukaiyama

  DOI：10.1246/cl.1974.1189

  日期：1974.10.5

  It was established that, in the presence of TiCl4, diketene [1] reacts with acetals [2] at −78∼−20°C to afford δ-alkoxy-β-ketoesters [3] in good yields. This reaction provides a novel method for the introduction of –COCH2COCH2– unit to an electrophile as acetal activated by TiCl4.

  已经确定，在 TiCl4 存在下，双烯酮 [1] 与缩醛 [2] 在 -78~-20°C 反应以良好的产率提供 δ-烷氧基-β-酮酯 [3]。该反应提供了一种将–COCH2COCH2–单元作为由TiCl4活化的缩醛引入亲电子试剂的新方法。
• Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine
  作者：Rosaria Villano、Maria R. Acocella、Arrigo Scettri

  DOI：10.1016/j.tet.2011.02.036

  日期：2011.4

  The synthesis of multifunctionalized beta-ketoesters has been achieved by using molecular iodine as a catalyst under very mild conditions. The vinylogous addition of Chan's diene 1 to carbonyl and carbonyl-related compounds (aldehydes, ketones, imines and acetals) occurred with high efficiencies and with complete gamma-selectivity, giving a useful method for the synthesis of interesting libraries of different delta-functionalized beta-ketoesters. (C) 2011 Elsevier Ltd. All rights reserved.