N-phenethyl-2,2-diphenylacetamide | 300717-27-5

• 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: N-phenethyl-2,2-diphenylacetamide
• 英文别名: 2,2-diphenyl-N-(2-phenylethyl)acetamide
• CAS: 300717-27-5
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: RLMGKXOWTFSAAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  草酰氯 、 N-phenethyl-2,2-diphenylacetamide 在 苯 作用下， 生成 1-phenethyl-4,4-diphenyl-pyrrolidine-2,3,5-trione
  参考文献：
  名称：

  Trialkylpyrrolidinetriones

  摘要：

  DOI：

  10.1021/ja01168a057
• 作为产物：
  描述：

  2,2-二苯基乙酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 N-phenethyl-2,2-diphenylacetamide
  参考文献：
  名称：

  Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest

  摘要：

  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.

  DOI：

  10.1021/ja042913p

文献信息

• Tetrabenzylpyrophosphate: An Efficient Catalyst for the Synthesis of Carboxamides from Carboxylic Acids and Amines
  作者：Y. Thirupathi Reddy、P. Narsimha Reddy、P. Raghotham Reddy、Peter A Crooks

  DOI：10.1246/cl.2008.528

  日期：2008.5.5

  An efficient method for the synthesis of simple and sterically hindered carboxamides from various carboxylic acids and amines using tetrabenzylpyrophosphate (TBPP) as a coupling agent in the presence of 4-(dimethylamino)pyridine (DMAP) is described. The reaction is operationally straightforward, proceeds under mild conditions at room temperature, and affords the desired product in high yield.

  描述了一种高效的方法，利用四苄基焦磷酸酯（TBPP）作为耦合剂，在4-(二甲氨基)吡啶（DMAP）存在下，从各种羧酸和胺合成简单及立体阻碍的羧酰胺。该反应操作简便，在室温下温和条件下进行，并以高产率获得所需产物。
• Facile direct synthesis of amides from trichloroethyl esters using catalytic DBU
  作者：Minh Thanh La、Hee-Kwon Kim

  DOI：10.1139/cjc-2018-0234

  日期：2018.12

  A practical method for the direct synthesis of amide compounds is described. Using small quantities of DBU as a catalyst, the direct conversion of 2,2,2-trichloroethyl esters to their corresponding...

  描述了直接合成酰胺化合物的实用方法。使用少量 DBU 作为催化剂，将 2,2,2-三氯乙酯直接转化为相应的...
• 2-Furanylboronic Acid as an Effective Catalyst for the Direct Amidation of Carboxylic Acids at Room Temperature
  作者：Eric Kwok Wai Tam、Rita、Lionel Yiqian Liu、Anqi Chen

  DOI：10.1002/ejoc.201403468

  日期：2015.2

  2-Furanylboronic acid has been identified as an inexpensive and effective catalyst for the dehydrative amide formation of carboxylic acids and amines. This transformation can be efficiently carried out at room temperature and is applicable to a wide range of carboxylic acids with primary and secondary amines to afford amides in good to excellent yields.

  2-呋喃基硼酸已被确定为一种廉价且有效的催化剂，用于羧酸和胺的脱水酰胺形成。这种转化可以在室温下有效地进行，并且适用于具有伯胺和仲胺的各种羧酸，以良好到极好的收率提供酰胺。
• [EN] COMPOUNDS AND METHODS FOR TREATMENT OF CANCER AND MODULATION OF PROGRAMMED CELL DEATH FOR MELANOMA AND OTHER CANCER CELLS<br/>[FR] COMPOSES ET PROCEDES DE TRAITEMENT DU CANCER ET MODULATION DE LA MORT CELLULAIRE PROGRAMMEE DE MELANOMES ET D'AUTRES CELLULES CANCEREUSES
  申请人：UNIV ALABAMA

  公开号：WO2005044191A3

  公开（公告）日：2005-10-20
• US7632972B2
  申请人：——

  公开号：US7632972B2

  公开（公告）日：2009-12-15