2-allyl-3-(3-methoxyphenyl)propionic acid | 757950-83-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-allyl-3-(3-methoxyphenyl)propionic acid
• 英文别名: 2-[(3-Methoxyphenyl)methyl]pent-4-enoic acid；2-[(3-methoxyphenyl)methyl]pent-4-enoic acid
• CAS: 757950-83-7
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: KGVVLUYASWIGHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-allyl-3-(3-methoxyphenyl)propionic acid 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 三氟甲磺酸 、 叠氮磷酸二苯酯 、 苄基三丁基氯化铵 、 碳酸氢钠 、 sodium iodide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 三乙胺 、 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 21. synthesis of CGP 49823

  摘要：

  CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization / Ritter reaction, gave trans 2-benzyl-4-acetamido-piperidines with high diastereoselectivity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00563-x
• 作为产物：
  描述：

  3-甲氧基氯苄 在 sodium hydroxide 、 硫酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-allyl-3-(3-methoxyphenyl)propionic acid
  参考文献：
  名称：

  SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 21. synthesis of CGP 49823

  摘要：

  CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization / Ritter reaction, gave trans 2-benzyl-4-acetamido-piperidines with high diastereoselectivity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00563-x

文献信息

• Iodine(III)-mediated aromatic amidation vs olefin amidohydroxylation. The amide N-substituent makes the difference
  作者：Sonia Serna、Imanol Tellitu、Esther Domı́nguez、Isabel Moreno、Raúl SanMartin

  DOI：10.1016/j.tet.2004.06.007

  日期：2004.7

  and an allyl group have been treated with phenyliodine(III)bis(trifluoroacetate) to generate stabilized N-acylnitrenium intermediates. It has been observed that, when starting from N-methoxy substituted amides, such intermediates are intramolecularly trapped by nucleophilic arene rings to render the quinolinone skeleton. Alternatively, under the same reaction conditions, N-para-methoxyphenylamides afford

  一系列Ñ甲氧基和ñ -对在由一个苄基和烯丙基α位置-methoxyphenylacetamides同时取代已经phenyliodine处理（III）双（三氟乙酸盐），以产生稳定的Ñ -acylnitrenium中间体。已经观察到，当从N-甲氧基取代的酰胺开始时，这些中间体在分子内被亲核芳烃环捕获以形成喹啉酮骨架。可替换地，在相同的反应条件下，ñ -对-methoxyphenylamides通过烯烃amidohydroxylation过程得到吡咯烷酮衍生物。
• SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 21. synthesis of CGP 49823
  作者：Siem J. Veenstra、Kathleen Hauser、Walter Schilling、Claudia Betschart、Silvio Ofner

  DOI：10.1016/s0960-894x(96)00563-x

  日期：1996.12

  CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization / Ritter reaction, gave trans 2-benzyl-4-acetamido-piperidines with high diastereoselectivity. Copyright (C) 1996 Elsevier Science Ltd