N-benzyl-2,2,2-triphenylacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-benzyl-2,2,2-triphenylacetamide
• 化学式: C₂₇H₂₃NO
• 分子量: 377.486
• InChiKey: JNTFGGFMZOLIEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三苯基乙酸 在 potassium carbonate 、 Selectfluor 、 三乙胺 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 N-benzyl-2,2,2-triphenylacetamide
  参考文献：
  名称：

  铜/ Selectfluor系统的酯介导的自由基介导的活化：大体积酰胺和肽的合成

  摘要：

  在本文中，我们描述了一种通过铜/ Selectfluor系统实现的自由基介导的过程来活化酯的新方法。衍生自庞大的羧酸和氨基酸的多种对甲氧基苄基酯可轻松转化为相应的酰基氟，直接用于酰胺和多肽的一锅法合成中。作为概念的证明，该方法被应用于空间位阻酰胺键的迭代形成。

  DOI：

  10.1021/acs.joc.1c00188

文献信息

• Radical-Mediated Activation of Esters with a Copper/Selectfluor System: Synthesis of Bulky Amides and Peptides
  作者：Akira Matsumoto、Zhe Wang、Keiji Maruoka

  DOI：10.1021/acs.joc.1c00188

  日期：2021.4.2

  approach for the activation of esters via a radical-mediated process enabled by a copper/Selectfluor system. A variety of para-methoxybenzyl esters derived from bulky carboxylic acids and amino acids can be easily converted into the corresponding acyl fluorides, directly used in the one-pot synthesis of amides and peptides. As a proof of concept, this method was applied to the iterative formation of sterically

  在本文中，我们描述了一种通过铜/ Selectfluor系统实现的自由基介导的过程来活化酯的新方法。衍生自庞大的羧酸和氨基酸的多种对甲氧基苄基酯可轻松转化为相应的酰基氟，直接用于酰胺和多肽的一锅法合成中。作为概念的证明，该方法被应用于空间位阻酰胺键的迭代形成。
• Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest
  作者：Robin S. Dothager、Karson S. Putt、Brittany J. Allen、Benjamin J. Leslie、Vitaliy Nesterenko、Paul J. Hergenrother

  DOI：10.1021/ja042913p

  日期：2005.6.1

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.
• Indifference to Hydrogen Bonding in a Family of Secondary Amides
  作者：D. Tyler McQuade、Sonya L. McKay、Douglas R. Powell、Samuel H. Gellman

  DOI：10.1021/ja9711019

  日期：1997.9.1

  N-H stretch region IR spectroscopy has been used to probe the hydrogen bond-donating properties of six structurally related secondary amides in which the amide group is flanked by sterically bulky groups. For three of the compounds, solid state IR analysis reveals N-R stretch bands >3400 cm(-1), which suggests the absence of intermolecular N-H-O=C hydrogen bonds. Crystallographic data for these three amides confirm the absence of a standard N-H-O=C interaction. For the other three amides, N-H stretch bands in the range 3370-3290 cm(-1) suggest the occurrence of intermolecular N-H-O=C hydrogen bonds in the solid state, but high quality crystals could not be grown. Steric hindrance to hydrogen bond donation by these amides is manifested in IR data obtained in DMSO: although this solvent is a strong hydrogen bond acceptor, N-H stretch bands are observed for both solvent-hydrogen bonded and non-hydrogen bonded amide groups. The amides described here and related compounds should be useful for calibrating spectroscopic methods that are intended to detect hydrogen bond formation.