5-[methyl(4-tolyl)carbamoyl]pentanoic acid

• 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: 5-[methyl(4-tolyl)carbamoyl]pentanoic acid
• 英文别名: 6-(N,4-dimethylanilino)-6-oxohexanoic acid
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD15498448
• 分子量: 249.31
• InChiKey: QJSJXDCPNMFCKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[methyl(4-tolyl)carbamoyl]pentanoic acid 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (trans)-N,N’-dimethyl-N-4-tolyl-N’-4-methoxyphenyl-2-oxo-cyclopentane-1,3-dicarboxamide
  参考文献：
  名称：

  Substrate scope in the copper-mediated construction of bis-oxindoles via a double C–H/Ar–H coupling process

  摘要：

  The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)(2)center dot H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.060
• 作为产物：
  描述：

  己二酸 、 N-甲基-对甲基苯胺 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到5-[methyl(4-tolyl)carbamoyl]pentanoic acid
  参考文献：
  名称：

  Substrate scope in the copper-mediated construction of bis-oxindoles via a double C–H/Ar–H coupling process

  摘要：

  The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)(2)center dot H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.060

文献信息

• Compounds and Compositions for Delivering Active Agents
  申请人：Gomez-Orellana Maria Isabel

  公开号：US20080255250A1

  公开（公告）日：2008-10-16

  Compounds and compositions for the delivery of active agents are provided. Methods of administration and preparation are provided as well.

  提供用于传递活性成分的化合物和组合物。同时提供了管理和制备的方法。
• Copper-Mediated Construction of Spirocyclic Bis-oxindoles via a Double C–H, Ar–H Coupling Process
  作者：Pauline Drouhin、Timothy E. Hurst、Adrian C. Whitwood、Richard J. K. Taylor

  DOI：10.1021/ol5024129

  日期：2014.9.19

  A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)(2).H2O/KOtBu in DMF at 110 degrees C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.
• Compounds and compositions for delivering active agents
  申请人：Emisphere Technologies, Inc.

  公开号：EP1756039B1

  公开（公告）日：2012-10-17
• US8273794B2
  申请人：——

  公开号：US8273794B2

  公开（公告）日：2012-09-25
• Substrate scope in the copper-mediated construction of bis-oxindoles via a double C–H/Ar–H coupling process
  作者：Pauline Drouhin、Timothy E. Hurst、Adrian C. Whitwood、Richard J.K. Taylor

  DOI：10.1016/j.tet.2015.02.060

  日期：2015.9

  The synthesis of bis-oxindoles via the copper(II)-mediated double cyclisation of linear bis-anilides is described. Cu(OAc)(2)center dot H2O was identified as an efficient and inexpensive catalyst for this process. In contrast to previous methods, which rely on the synthesis of the central core from existing oxindole building blocks, this new approach focusses on concurrent formation of both oxindole rings from a simple linear precursor, allowing the formation of bis-oxindoles containing a diverse range of cyclic and acyclic linkers using a single synthetic method. (C) 2015 Elsevier Ltd. All rights reserved.