N-(2-亚硝基苯基)-乙酰胺 | 21354-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-亚硝基苯基)-乙酰胺
• 英文名称: 2-nitrosoacetanilide
• 英文别名: N-(2-Nitrosophenyl)acetamide
• CAS: 21354-01-8
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: AEMQSBVTDQQBGB-UHFFFAOYSA-N

物化性质

• 熔点：
  105-110 °C
• 沸点：
  376.2±25.0 °C(Predicted)
• 密度：
  1.351 g/cm3(Temp: 15 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(2-亚硝基苯基)-乙酰胺 在 吡啶 、 氢氧化钾 、 溶剂黄146 、 甲胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 N-{2-[3-(2-picolinoylaminophenylazo)phenylazo]phenyl}picolinamide
  参考文献：
  名称：

  Helical Conformational Dynamics and Photoisomerism of Alternating Pyridinedicarboxamide/m-(Phenylazo)azobenzene Oligomers

  摘要：

  Alternating sequences of pyridine-2,6-dicarboxamides and meta-(phenylazo)azobenzenes have been assembled into oligomers composed of four (8) and eight (9) azobenzene linkages. X-ray crystallography confirmed that oligomer 8 adopts a two-turn helical conformation with a helical pitch of approximately 3.4 angstrom in the solid state. The presence of a two- and four-turn helical conformation of 8 and 9, respectively, in polar and nonpolar solvents was elucidated by the anisotropic upfield shifting of protons located within the helices, NOE enhancements between protons oriented toward the helix interior, and the diastereotopicity of the terminal benzyloxycarbonyl (CBz) methylene protons. H-1 NMR line shape analysis of the CBz methylene hydrogens at the chain ends revealed a dynamic equilibria interconverting M and P helical conformations with energetic barriers (Delta G(double dagger)) of 11.1 (AS(double dagger) = -19.4 +/- 1.6 cal mol(-1) K-1; Delta H-double dagger = 6.5 +/- 0.4 kcal/mol) for 8 and 13.8 kcal/mol (Delta S-double dagger = -6.6 +/- 6.2 cal mol(-1) K-1; Delta H-double dagger = 11.8 +/- 1.8 kcal/mol) for 9. Irradiation of the oligomers with 350 nm light induces an E -> Z isomerization of the azo linkages that decreases in efficacy at longer helix lengths. The suppression of E -> Z isomerization is a consequence of the contrasting behavior of the azo linkages located at the helix termini, which afford Z/E ratios similar to those of model compound 7d, and the internal azo groups, which undergo significantly lower Z/E conversion ratios compared with 7e.

  DOI：

  10.1021/ja0547228
• 作为产物：
  描述：

  2-硝基苯胺 在 Rh on carbon 溶剂黄146 、 肼 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 N-(2-亚硝基苯基)-乙酰胺
  参考文献：
  名称：

  Helical Conformational Dynamics and Photoisomerism of Alternating Pyridinedicarboxamide/m-(Phenylazo)azobenzene Oligomers

  摘要：

  Alternating sequences of pyridine-2,6-dicarboxamides and meta-(phenylazo)azobenzenes have been assembled into oligomers composed of four (8) and eight (9) azobenzene linkages. X-ray crystallography confirmed that oligomer 8 adopts a two-turn helical conformation with a helical pitch of approximately 3.4 angstrom in the solid state. The presence of a two- and four-turn helical conformation of 8 and 9, respectively, in polar and nonpolar solvents was elucidated by the anisotropic upfield shifting of protons located within the helices, NOE enhancements between protons oriented toward the helix interior, and the diastereotopicity of the terminal benzyloxycarbonyl (CBz) methylene protons. H-1 NMR line shape analysis of the CBz methylene hydrogens at the chain ends revealed a dynamic equilibria interconverting M and P helical conformations with energetic barriers (Delta G(double dagger)) of 11.1 (AS(double dagger) = -19.4 +/- 1.6 cal mol(-1) K-1; Delta H-double dagger = 6.5 +/- 0.4 kcal/mol) for 8 and 13.8 kcal/mol (Delta S-double dagger = -6.6 +/- 6.2 cal mol(-1) K-1; Delta H-double dagger = 11.8 +/- 1.8 kcal/mol) for 9. Irradiation of the oligomers with 350 nm light induces an E -> Z isomerization of the azo linkages that decreases in efficacy at longer helix lengths. The suppression of E -> Z isomerization is a consequence of the contrasting behavior of the azo linkages located at the helix termini, which afford Z/E ratios similar to those of model compound 7d, and the internal azo groups, which undergo significantly lower Z/E conversion ratios compared with 7e.

  DOI：

  10.1021/ja0547228

文献信息

• Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
  作者：Silvia Roscales、Aurelio G. Csákÿ

  DOI：10.1021/acs.orglett.8b00473

  日期：2018.3.16

  The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.

  据报道，通过亚硝基芳烃和硼酸之间的无过渡金属交叉偶联来合成二（杂）芳基胺。该方法实验上简单，快速，温和且可扩展，并且具有宽泛的官能团耐受性，包括羰基，硝基，卤素，游离的OH和NH基团。它还允许合成位阻化合物。
• Synthesis and Property Studies of Cyclotrisazobenzenes
  作者：Raphael Reuter、Nik Hostettler、Markus Neuburger、Hermann A. Wegner

  DOI：10.1002/ejoc.200900861

  日期：2009.11

  special interest due to their unique photochromic behavior. Cyclotrisazobenzenes 2 (R = H, Br, tBu) were prepared to probe how much strain the photoisomerization of the azobenzene motive can tolerate. The macrocycles were synthesized in an overall yield of 10–20 % from ortho-phenylenediamine (6). Solid-state structures of cyclotrisazobenzenes 2a and 2b were obtained. Irradiation under various conditions

  Azobenzenophanes 是迷人的大环化合物，由于其独特的光致变色行为而受到特别关注。制备环三偶氮苯 2 (R = H, Br, tBu) 以探测偶氮苯动机的光异构化可以承受多大的应变。从邻苯二胺 (6) 合成大环化合物的总产率为 10-20%。获得了环三偶氮苯 2a 和 2b 的固态结构。在各种条件下辐照不会引起任何异构化。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• Insights into a novel class of azobenzenes incorporating 4,6-<i>O</i>-protected sugars as photo-responsive organogelators
  作者：P. V. Bhavya、V. Rabecca Jenifer、Panneerselvam Muthuvel、T. Mohan Das

  DOI：10.1039/c9ra08033c

  日期：——

  A novel class of 4,6-O-butylidene/ethylidene/benzylidene β-D-glucopyranose gelator functionalized with photo-responsive azobenzene moieties were designed and synthesized and also characterized using different spectral techniques. These azobenzene-based organogelators can gel even at lower concentrations (critical gelation concentration – 0.5% and 1%). A morphological study of the gels shows one-dimensional

  设计和合成了一种新型的 4,6 - O-丁叉/亚乙叉/亚苄基 β- D-吡喃葡萄糖凝胶剂，并使用不同的光谱技术对其进行了表征。这些基于偶氮苯的有机凝胶剂即使在较低浓度（临界凝胶浓度 - 0.5% 和 1%）下也能凝胶化。凝胶的形态学研究显示一维聚集束和螺旋纤维。自组装的主要驱动力是通过不同群体表现出的合作相互作用，即。、糖羟基（氢键相互作用）、偶氮苯（芳族π-π相互作用）和烷基链的保护基团（范德华相互作用）。
• Oligoazobenzenes – Switching in a New Dimension
  作者：Raphael Reuter、Nik Hostettler、Markus Neuburger、Hermann A. Wegner

  DOI：10.2533/chimia.2010.180

  日期：——

  A new synthesis of cyclotrisazobenzene with different substituents was developed with yields of up to 30%. Solid-state structures of cyclotrisazobenzene as well as the tert-butyl derivative were obtained. Also, the photochromic properties and the complexation behaviour with alkali metal ions of this class of molecules were investigated.

  一种新的环三偶氮苯衍生物合成方法被开发出来，产率可达30%。得到了环三偶氮苯及叔丁基衍生物的固态结构。此类分子的光致变色性质和与碱金属离子的络合行为也得到了研究。
• Syntheses and Cyclization Reactions of Bifunctional 1,2-Bis (styryl)benzenes and Some Aza Analogues. Macrocyclic aza compounds. V
  作者：Carl-Peter Ehrensperger、Manfred Heberlein、Peter Skrabal

  DOI：10.1002/hlca.19780610808

  日期：1978.12.13

  The syntheses of the bis (styryl)benzenes 4 and 5 and of the aza analogue 3 are described. Diamine 3 and dialdehyde 5 were cyclized to the 14-membered macrocycles 19 and 27, respectively. Diamine 4 and glyoxal give the 28-membered macrocycle 28. The cyclizations are discussed.

  描述了双（苯乙烯基）苯4和5以及氮杂类似物3的合成。二胺3和二醛5分别环化成14元大环19和27。二胺4和乙二醛产生28元大环28。讨论了环化。