Ethyl 4-(pentanoylamino)benzoate | 86927-23-3

• 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: Ethyl 4-(pentanoylamino)benzoate
• CAS: 86927-23-3
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD02339517
• 分子量: 249.31
• InChiKey: FGUZNRRPWKFLCV-UHFFFAOYSA-N

物化性质

• 熔点：
  67 °C(Solv: ethanol (64-17-5))
• 沸点：
  422.2±28.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(pentanoylamino)benzoate 在 劳森试剂 、 4-dimethylaminopyridine borane 、 di-tert-butoxydiazene 、 苯硫酚 作用下， 以 甲苯 为溶剂， 生成 4-pentylamino-benzoic acid ethyl ester
  参考文献：
  名称：

  Lewis Base–Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides

  摘要：

  A new protocol for radical transformations of thioamides promoted by Lewis base-boryl radicals is reported. The desulfurizative reduction to access organic amines was enabled utilizing 4-dimethylaminopyridine-BH3 as the boryl radical precursor and PhSH as the polarity reversal catalyst. Alternatively, the chain process for unsaturated thioamides was switched to an annulation reaction using N-heterocyclic carbene BH3 as the boryl radical precursor and sterically bulky Ph3CSH as the catalyst, allowing for the construction of N-heterocyclic and carbocyclic skeletons.

  DOI：

  10.1021/acs.orglett.7b03201
• 作为产物：
  描述：

  戊酰氯 、 苯佐卡因 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Ethyl 4-(pentanoylamino)benzoate
  参考文献：
  名称：

  Lewis Base–Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides

  摘要：

  A new protocol for radical transformations of thioamides promoted by Lewis base-boryl radicals is reported. The desulfurizative reduction to access organic amines was enabled utilizing 4-dimethylaminopyridine-BH3 as the boryl radical precursor and PhSH as the polarity reversal catalyst. Alternatively, the chain process for unsaturated thioamides was switched to an annulation reaction using N-heterocyclic carbene BH3 as the boryl radical precursor and sterically bulky Ph3CSH as the catalyst, allowing for the construction of N-heterocyclic and carbocyclic skeletons.

  DOI：

  10.1021/acs.orglett.7b03201

文献信息

• General cross-coupling reactions with adaptive dynamic homogeneous catalysis
  作者：Indrajit Ghosh、Nikita Shlapakov、Tobias A. Karl、Jonas Düker、Maksim Nikitin、Julia V. Burykina、Valentine P. Ananikov、Burkhard König

  DOI：10.1038/s41586-023-06087-4

  日期：——

  (AD-HoC) with nickel under visible-light-driven redox reaction conditions for general C(sp2)–(hetero)atom coupling reactions. The self-adjustive nature of the catalytic system allowed the simple classification of dozens of various classes of nucleophiles in cross-coupling reactions. This is synthetically demonstrated in nine different bond-forming reactions (in this case, C(sp2)–S, Se, N, P, B, O, C(sp3, sp2

  交叉偶联反应是现代有机合成中最重要的转化之一1,2,3。尽管考虑到各种方案，报道的（杂）芳基卤化物和亲核试剂偶联配偶体的范围非常大，但化合物类别之间的反应条件差异很大，因此需要根据具体情况重新优化反应条件4。在这里，我们介绍了在可见光驱动的氧化还原反应条件下镍的自适应动态均相催化（AD-HoC），用于一般的 C( sp 2 )–(杂)原子偶联反应。催化系统的自我调节性质允许在交叉偶联反应中对数十种不同类别的亲核试剂进行简单分类。这在九种不同的成键反应（在本例中为 C( sp 2 )–S、Se、N、P、B、O、C( sp 3、  sp 2、  sp )、Si、Cl）中得到了综合证明在可预测的反应条件下进行数百个合成实例。催化反应中心和条件因添加的亲核试剂或如果需要而添加市售的廉价胺碱而彼此不同。
• SET or TET? Iron-catalyzed aminocarbonylation of unactivated alkyl halides with amines, amides, and indoles via a substrate dependent mechanism
  作者：Han-Jun Ai、Fengqian Zhao、Xiao-Feng Wu

  DOI：10.1016/s1872-2067(22)64208-6

  日期：2023.4

  abundance, and potential for distinct and complementary reactivity patterns. Meanwhile, alkyl bromides as well as low nucleophilic amides and indoles are considered to be particularly challenge substrates for carbonylation reactions. Herein, we report an iron-catalyzed carbonylative coupling of unactivated alkyl halides with amines, amides, and indoles to assemble amide structural units, affording various

  铁催化的羰基化反应在我们倡导可持续发展的化学界非常受欢迎，因为它成本低、资源丰富，并且具有独特和互补反应模式的潜力。同时，烷基溴以及低亲核性酰胺和吲哚被认为是羰基化反应特别具有挑战性的底物。在此，我们报告了未活化的烷基卤化物与胺、酰胺和吲哚的铁催化羰基化偶联以组装酰胺结构单元，提供各种酰胺、酰亚胺和N- 具有优异产率和前所未有的官能团相容性的酰基吲哚。值得注意的是，我们的方法也代表了 Fe 催化的卤代烷氨基羰基化的例子。我们的初步机理研究表明反应途径是底物依赖性的：当使用烷基碘时，羰基化通过自由基途径进行；而当烷基溴化物作为亲电子试剂时，会发生双电子转移 (TET) 过程。
• Lewis Base–Boryl Radicals Enabled the Desulfurizative Reduction and Annulation of Thioamides
  作者：You-Jie Yu、Feng-Lian Zhang、Jie Cheng、Jing-Hao Hei、Wei-Ting Deng、Yi-Feng Wang

  DOI：10.1021/acs.orglett.7b03201

  日期：2018.1.5

  A new protocol for radical transformations of thioamides promoted by Lewis base-boryl radicals is reported. The desulfurizative reduction to access organic amines was enabled utilizing 4-dimethylaminopyridine-BH3 as the boryl radical precursor and PhSH as the polarity reversal catalyst. Alternatively, the chain process for unsaturated thioamides was switched to an annulation reaction using N-heterocyclic carbene BH3 as the boryl radical precursor and sterically bulky Ph3CSH as the catalyst, allowing for the construction of N-heterocyclic and carbocyclic skeletons.