methyl 5-(4-nitrophenyl)-3-oxo-5-(phenylamino)pentanoate

• 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-(4-nitrophenyl)-3-oxo-5-(phenylamino)pentanoate
• 英文别名: Methyl 5-anilino-5-(4-nitrophenyl)-3-oxopentanoate；methyl 5-anilino-5-(4-nitrophenyl)-3-oxopentanoate
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: YQSUCIUNIKPNLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 、 (4-硝基苄基亚基)苯胺 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， 生成 methyl 5-(4-nitrophenyl)-3-oxo-5-(phenylamino)pentanoate
  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 approach to δ-amino-β-ketoesters by vinylogous Mannich reaction of masked acetoacetates
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tet.2007.09.073

  日期：2007.12

  SiCl4 is an efficient and selective catalyst for the vinylogous Mannich reaction of linear and cyclic synthetic equivalents of acetoacetate dianion, leading to delta-amino-beta-ketoesters in moderate to high yields and complete gamma-selectivity; anti-diastereoselectivity was observed by using a gamma-methyl-substituted cyclic silyloxydiene. (c) 2007 Elsevier Ltd. All rights reserved.