2-(4-methoxy-benzyl)-pent-4-enoic acid | 53979-32-1

• 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-(4-methoxy-benzyl)-pent-4-enoic acid
• 英文别名: 2-(4-Methoxy-benzyl)-pent-4-ensaeure；2-[(4-Methoxyphenyl)methyl]pent-4-enoic acid；2-[(4-methoxyphenyl)methyl]pent-4-enoic acid
• CAS: 53979-32-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: HPXUYEODQMWDKY-UHFFFAOYSA-N

物化性质

• 沸点：
  185-189 °C(Press: 6 Torr)
• 密度：
  1.08015 g/cm3

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-(4-methoxy-benzyl)-pent-4-enoic acid 在 硫酸 、 sulfur 作用下， 生成 6-methoxy-4-methyl-[2]naphthoic acid
  参考文献：
  名称：

  Darzens; Levy, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1935, vol. 200, p. 469

  摘要：

  DOI：
• 作为产物：
  描述：

  烯丙基丙二酸二乙酯 在 sodium hydroxide 、 硫酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-(4-methoxy-benzyl)-pent-4-enoic 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

• Catalyst-Controlled C–O versus C–N Allylic Functionalization of Terminal Olefins
  作者：Iulia I. Strambeanu、M. Christina White

  DOI：10.1021/ja405394v

  日期：2013.8.14

  The divergent synthesis of syn-1,2-aminoalcohol or syn-1,2-diamine precursors from a common terminal olefin has been accomplished using a combination of palladium(II) catalysis with Lewis acid cocatalysis. Palladium(II)/bis-sulfoxide catalysis with a silver triflate cocatalyst leads for the first time to anti-2-aminooxazolines (C-O) in good to excellent yields. Simple removal of the bis-sulfoxide ligand

  使用钯 (II) 催化与路易斯酸助催化的组合，已经完成了从共同的末端烯烃合成 1,2-氨基醇或syn-1,2-二胺前体的不同合成。使用三氟甲磺酸银助催化剂的钯 (II)/双亚砜催化首次以良好至极好的收率产生抗 2-氨基恶唑啉 (CO)。从该反应中简单地去除双亚砜配体导致反应性的完全转变，以良好的收率和出色的非对映选择性提供抗咪唑啉酮产物 (CN)。机理研究表明，由于从烯丙基 CH 裂解/官能化到烯烃异构化/氧化胺化的机制转换，来自常见环境亲核试剂的 CO 与 CN 反应性不同。
• <i>N</i>-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation
  作者：Thomas J. Osberger、M. Christina White

  DOI：10.1021/ja506036q

  日期：2014.8.6

  A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
• Arakeljan; Dangjan, Nauchnye Trudy, Erevanskii Gosudarstvennyi Universitet, Seriya Khimicheskikh Nauk, 1957, vol. 60, p. 17,18
  作者：Arakeljan、Dangjan

  DOI：——

  日期：——
• 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
• Darzens; Levy, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1935, vol. 200, p. 469
  作者：Darzens、Levy

  DOI：——

  日期：——