ethyl 5-(benzylamino)-5-oxopentanoate | 66001-97-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 5-(benzylamino)-5-oxopentanoate
• CAS: 66001-97-6
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: FRHUMYWYLVSHHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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 5-(benzylamino)-5-oxopentanoate 、 (3,4-二氢-1H-异色烯-1-甲基)胺盐酸盐 以64%的产率得到
  参考文献：
  名称：

  BADALYAN V. E.; SAMODUROVA A. G.; GERASIMYAN D. A.; MARTIROSYAN K. A.; MA+, AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1977, 30, HO 9, 762-770

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基(1S,2S)-2-甲酰基环丙烷羧酸酯 、 苄胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 以82%的产率得到ethyl 5-(benzylamino)-5-oxopentanoate
  参考文献：
  名称：

  Catalytic Redox Amidations of Aldehydes with a Polymer-Supported Peptide-N-Heterocyclic Carbene Multifunctional Catalyst

  摘要：

  We have prepared an oligomeric histidine-bound N-heterocyclic carbene precursor by coupling a carboxylic acid functionalized 1,2,4-triazolium salt to a peptide using solid-phase peptide synthesis. We have demonstrated that the resulting multifunctional resin-bound catalyst cooperatively facilitates redox amidation reactions of aldehydes and amines, a reaction not catalyzed by N-heterocyclic carbenes alone.

  DOI：

  10.1055/s-0033-1338956

文献信息

• Versatile Palladium-Catalyzed Approach to Acyl Fluorides and Carbonylations by Combining Visible Light- and Ligand-Driven Operations
  作者：Yi Liu、Cuihan Zhou、Meijing Jiang、Bruce A. Arndtsen

  DOI：10.1021/jacs.2c01951

  日期：2022.6.1

  We describe the development of a general palladium-catalyzed carbonylative method to synthesize acyl fluorides from aryl, heteroaryl, alkyl, and functionalized organic halides. Mechanistic analysis suggests that the reaction proceeds via the synergistic combination of visible light photoexcitation of Pd(0) to induce oxidative addition with a ligand-favored reductive elimination. These together create

  我们描述了从芳基、杂芳基、烷基和官能化有机卤化物合成酰基氟化物的一般钯催化羰基化方法的发展。机理分析表明，反应通过Pd(0) 的可见光光激发的协同组合进行，以诱导氧化加成和配体有利的还原消除。这些共同创造了一个单向催化循环，不受一氧化碳配位的经典效应的抑制。将酰氟的催化形成与其随后的亲核反应相结合，开辟了一种以前所未有的广度进行羰基化反应的方法，包括高度官能化的含羰基产物的组装。
• A Visible Light Driven Nickel Carbonylation Catalyst: The Synthesis of Acid Chlorides from Alkyl Halides
  作者：Kristian El Chami、Yi Liu、Mohammed A. Belahouane、Yiyang Ma、Pierre‐Louis Lagueux‐Tremblay、Bruce A. Arndtsen

  DOI：10.1002/anie.202213297

  日期：2023.3

  A visible light driven nickel carbonylation catalyst has been develop. This offers a method for carbonylative coupling reactions with an earth abundant metal at ambient temperature for the conversion of alkyl halides into synthetically versatile acid chlorides. The acid chlorides can then be transformed into an array of challenging ester, thioester and amide products.

  已经开发出可见光驱动的镍羰基化催化剂。这提供了一种在环境温度下与地球上丰富的金属进行羰基化偶联反应的方法，用于将卤代烷转化为合成用途广泛的酰氯。然后可以将酰氯转化为一系列具有挑战性的酯、硫酯和酰胺产品。
• N-Heterocyclic Carbene-Catalyzed Redox Amidations of α-Functionalized Aldehydes with Amines
  作者：Jeffrey W. Bode、Stephanie S. Sohn

  DOI：10.1021/ja0768136

  日期：2007.11.1

  A catalytic method for the direct synthesis of carboxylic acid amides from amines and alpha-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product.
• Catalytic Redox Amidations of Aldehydes with a Polymer-Supported Peptide-N-Heterocyclic Carbene Multifunctional Catalyst
  作者：Chenaimwoyo Gondo、Jeffrey Bode

  DOI：10.1055/s-0033-1338956

  日期：——

  We have prepared an oligomeric histidine-bound N-heterocyclic carbene precursor by coupling a carboxylic acid functionalized 1,2,4-triazolium salt to a peptide using solid-phase peptide synthesis. We have demonstrated that the resulting multifunctional resin-bound catalyst cooperatively facilitates redox amidation reactions of aldehydes and amines, a reaction not catalyzed by N-heterocyclic carbenes alone.
• BADALYAN V. E.; SAMODUROVA A. G.; GERASIMYAN D. A.; MARTIROSYAN K. A.; MA+, AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1977, 30, HO 9, 762-770
  作者：BADALYAN V. E.、 SAMODUROVA A. G.、 GERASIMYAN D. A.、 MARTIROSYAN K. A.、 MA+

  DOI：——

  日期：——