2-cyano-N-[2-(phenyl)phenyl]acetamide | 127563-49-9

• 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: 2-cyano-N-[2-(phenyl)phenyl]acetamide
• 英文别名: 2-cyano-N-(4-biphenyl)acetamide；cyanoacetamido-2 biphenyle；cyano-acetic acid biphenyl-2-ylamide；N-(Biphenylyl-(2))-C-cyan-acetamid；Cyan-essigsaeure-biphenyl-2-ylamid；2-cyano-N-(2-phenylphenyl)acetamide
• CAS: 127563-49-9
• 化学式: C₁₅H₁₂N₂O
• mdl: MFCD09931288
• 分子量: 236.273
• InChiKey: RVBGFCDGQNOTQM-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  451.8±28.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-cyano-N-[2-(phenyl)phenyl]acetamide 在 哌啶 、 氢气 作用下， 以 乙醇 为溶剂， 50.0~120.0 ℃ 、1.0 MPa 条件下， 反应 1.0h， 生成 3-amino-2-(thiophene-2-ylmethyl)-N-(4-biphenyl)propanamide
  参考文献：
  名称：

  异吲哚-7-羧酸和7-氧杂双环[2.2.1]庚烷的化学选择流动氢化方法†

  摘要：

  通过一系列连续的化学选择性流加氢和无溶剂转化，访问了两个修饰度很高的降冰藓素类似物的文库。使用10％的Pd / C催化剂，对反应参数（H 2压力，温度和流速条件）的修改允许在呋喃，苄基和腈部分存在下容易地进行选择性直接还原胺化和烯烃还原。使用20％Pd（OH）2 / C; 钯四; 5％Pt / C（硫化）得到呋喃和烯烃（均还原）和烯烃还原产物的混合物。RuO 2 ; 0.5％的Re / C和Re 2 O 7没有减少。通过使用RANEY®镍催化剂，在呋喃部分存在下，烯烃和腈同时还原。总共使用不到200毫克的试剂检查了31种反应条件，从而可以有效地确定最佳条件。这些优化的氢化条件以接近定量的产率提供了所需的类似物，从而消除了反应后处​​理和色谱分离的要求。

  DOI：

  10.1039/c3ra47657j
• 作为产物：
  描述：

  2-氨基联苯 、 氰乙酸甲酯 以7%的产率得到2-cyano-N-[2-(phenyl)phenyl]acetamide
  参考文献：
  名称：

  α-Cyanocinnamide derivatives: a new family of non-peptide, non-sulfhydryl inhibitors of ras farnesylation

  摘要：

  Farnesylation of Ras and other proteins is required for their membrane attachment and normal function. Here we report on the synthesis of alpha-cyanocinnamide derivatives, a new family of farnesyltransferase inhibitors. These compounds are nonpeptidic and do not contain sulfhydryl groups. The most potent compound is a pure competitive inhibitor with respect to the Ras protein and mixed competitive with respect to farnesyl diphosphate. Selectivity studies against geranylgeranyltransferase and biological activities of selected compounds are described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00118-2

文献信息

• Nickel-promoted oxidative domino C_sp3–H/N–H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones
  作者：Li-Rong Wen、Ning-Ning Wang、Wu-Bo Du、Qiang Ma、Lin-Bao Zhang、Ming Li

  DOI：10.1039/d1ob00139f

  日期：——

  double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2 as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3–H bond, representing an effective

  乙酰胺与异氰酸酯的第一个镍催化的氧化多米诺骨牌C sp3 -H / N-H双异氰酸酯插入反应已被开发用于吡咯烷-2-酮衍生物的合成。通过利用Ni（acac）2作为催化剂，各种带有各种官能团的乙酰胺与该反应体系相容。在此转化过程中，异氰酸酯可以用作C1连接器，并插入无活性的C sp3- H键，代表构建杂环的有效方法。
• Low Molecular Weight Amidoximes that Act as Potent Inhibitors of Lysine-Specific Demethylase 1
  作者：Stuart Hazeldine、Boobalan Pachaiyappan、Nora Steinbergs、Shannon Nowotarski、Allison S. Hanson、Robert A. Casero、Patrick M. Woster

  DOI：10.1021/jm3002845

  日期：2012.9.13

  The recently discovered enzyme lysine-specific demethylase 1 (LSD1) plays an important role in the epigenetic control of gene expression, and aberrant gene silencing secondary to LSD1 dysregulation is thought to contribute to the development of cancer. We reported that (bis)guanidines, (bis)biguanides, and their urea- and thiourea isosteres are potent inhibitors of LSD1 and induce the re-expression of aberrantly silenced tumor suppressor genes in tumor cells in vitro. We now report a series of small molecule amidoximes that are moderate inhibitors of recombinant LSD1 but that produce dramatic changes in methylation at the histone 3 lysine 4 (H3K4) chromatin mark, a specific target of LSD1, in Calu-6 lung carcinoma cells. In addition, these analogues increase cellular levels of secreted frizzle-related protein (SFRP) 2, H-cadherin (HCAD), and the transcription factor GATA4. These compounds represent leads for an important new series of drug-like epigenetic modulators with the potential for use as antitumor agents.
• Lion, C.; Boukou-Poba, J. P.; Charvy, C., Bulletin des Societes Chimiques Belges, 1989, vol. 98, # 8, p. 557 - 566
  作者：Lion, C.、Boukou-Poba, J. P.、Charvy, C.

  DOI：——

  日期：——
• Synthetical experiments in the group of sympathomimetics, part IV
  作者：S. Rajagopalan

  DOI：10.1007/bf03048965

  日期：1944.2
• LION, C.;BOUKOU-POBA, J. P.;CHARVY, C., BULL. SOC. CHIM. BELG., 98,(1989) N, C. 557-566
  作者：LION, C.、BOUKOU-POBA, J. P.、CHARVY, C.

  DOI：——

  日期：——