2,6-dinitroacetanilide | 90110-78-4

• 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: 2,6-dinitroacetanilide
• 英文别名: acetic acid-(2,6-dinitro-anilide)；Essigsaeure-(2,6-dinitro-anilid)；2,6-Dinitro-acetanilid；N-(2,6-Dinitrophenyl)acetamide
• CAS: 90110-78-4
• 化学式: C₈H₇N₃O₅
• 分子量: 225.161
• InChiKey: GIZBJZXZVWGAPV-UHFFFAOYSA-N

物化性质

• 熔点：
  196-197 °C
• 沸点：
  438.5±35.0 °C(Predicted)
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 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：
  121
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-dinitroacetanilide 在 盐酸 、 tin 作用下， 生成 2-甲基-1H-苯并咪唑-7-胺
  参考文献：
  名称：

  Salkowski, Chemische Berichte, 1877, vol. 10, p. 1696

  摘要：

  DOI：
• 作为产物：
  描述：

  2-硝基苯胺 在 氧气 、 二氧化氮 、 臭氧 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 2,6-dinitroacetanilide
  参考文献：
  名称：

  Suzuki, Hitomi; Tatsumi, Atsuo; Ishibashi, Taro, Journal of the Chemical Society. Perkin transactions I, 1995, # 4, p. 339 - 344

  摘要：

  DOI：

文献信息

• Ortho-selective nitration of acetanilides with nitrogen dioxide in the presence of ozone
  作者：Hitomi Suzuki、Taro Ishibashi、Takashi Murashima、Kenkichi Tsukamoto

  DOI：10.1016/0040-4039(91)80229-y

  日期：1991.11

  In the presence of ozone, nitrogen dioxide rapidly reacts with acetanilides ortho-selectively at low temperatures, giving a high proportion of ortho-nitro derivatives in good yields.

  在臭氧的存在下，二氧化氮在低温下与邻苯二甲酰胺快速进行邻位选择性反应，从而以高收率得到高比例的邻硝基衍生物。
• Nitration of <i>N</i>-acetyl anilides using silver(I) nitrate/persulfate combination
  作者：Hathaichanok Sanjeam、Chutima Kuhakarn、Pawaret Leowanawat、Vichai Reutrakul、Darunee Soorukram

  DOI：10.1080/00397911.2022.2081924

  日期：2022.5.19

  Abstract Nitration of N-acetyl anilides using a simple combination of AgNO3 and K2S2O8 as a stable nitro source and an oxidant, respectively, was explored. The reaction was practical to operate and proceeded under considerably mild reaction conditions (reflux in acetonitrile) within acceptable reaction time (6 h). The para-substituted N-acetyl anilides gave only ortho-nitrated products in moderate

  摘要 探索了使用AgNO 3和K 2 S 2 O 8的简单组合分别作为稳定的硝基源和氧化剂对N-乙酰苯胺的硝化。该反应在可接受的反应时间(6小时)内可在相当温和的反应条件(在乙腈中回流)下实际操作和进行。对位取代的N-乙酰苯胺仅产生邻位硝化产物，产率适中（产率 30-63%）。邻位、间位或未取代的N-乙酰苯胺产生硝化产物的混合物（30-72％的总产率），优先在对位而不是邻位（邻位：对位；1.0：1.1-1.0：2.8）。
• POLLUTION-FREE PROCESS FOR PRODUCING AROMATIC NITRO COMPOUND WITHOUT USING MINERAL ACID
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP0497989A1

  公开（公告）日：1992-08-12

  A process for producing aromatic nitro compound which comprises nitrating an aromatic compound by blowing oxygen or air containing a nitrogen oxide and ozone into a solution or suspension thereof in an organohalogen solvent. The use of the oxygen or air containing a nitrogen oxide and ozone as the nitrating agent makes it possible to produce an aromatic nitro compound under mild conditions without using any inorganic acid and to remove various troubles accompanying the use of an inorganic acid in the conventional production process.

  一种生产芳香族硝基化合物的工艺，包括将氧气或含有氧化氮和臭氧的空气吹入芳香族化合物在有机卤素溶剂中的溶液或悬浮液中，使芳香族化合物硝化。使用含有氧化氮和臭氧的氧气或空气作为硝化剂，可以在温和的条件下生产芳香族硝基化合物，而无需使用任何无机酸，并消除了在传统生产工艺中使用无机酸所带来的各种麻烦。
• On the active site for hydrolysis of aryl amides and choline esters by human cholinesterases
  作者：Sultan Darvesh、Robert S. McDonald、Katherine V. Darvesh、Diane Mataija、Sam Mothana、Holly Cook、Karina M. Carneiro、Nicole Richard、Ryan Walsh、Earl Martin

  DOI：10.1016/j.bmc.2006.02.021

  日期：2006.7

  Cholinesterases, in addition to their well-known esterase action, also show an aryl acylamidase (AAA) activity whereby they catalyze the hydrolysis of amides of certain aromatic amines. The biological function of this catalysis is not known. Furthermore, it is not known whether the esterase catalytic site is involved in the AAA activity of cholinesterases. It has been speculated that the AAA activity, especially that of butyrylcholinesterase (BuChE), may be important in the development of the nervous system and in pathological processes such as formation of neuritic plaques in Alzheimer's disease (AD). The substrate generally used to study the AAA activity of cholinesterases is N-(2-nitrophenyl)acetamide. However, use of this substrate requires high concentrations of enzyme and substrate, and prolonged periods of incubation at elevated temperature. As a consequence, difficulties in performing kinetic analysis of AAA activity associated with cholinesterases have hampered understanding this activity. Because of its potential biological importance, we sought to develop a more efficient and specific substrate for use in studying the AAA activity associated with BuChE, and for exploring the catalytic site for this hydrolysis. Here, we describe the structure-activity relationships for hydrolysis of anilides by cholinesterases. These studies led to a substrate, N-(2-nitrophenyl)trifluoroacetamide, that was hydrolyzed several orders of magnitude faster than N-(2-nitrophenyl)acetamide by cholinesterases. Also, larger N-(2-nitrophenyl)alkylamides were found to be more rapidly hydrolyzed by BuChE than N-(2-nitrophenyl)acetamide and, in addition, were more specific for hydrolysis by BuChE. Thus, N-(2-nitrophenyl)alkylamides with six to eight carbon atoms in the acyl group represent suitable specific substrates to investigate further the function of the AAA activity of BuChE. Based on the substrate structure-activity relationships and kinetic studies, the hydrolysis of anilides and esters of choline appears to utilize the same catalytic site in BuChE. (c) 2006 Elsevier Ltd. All rights reserved.
• Rosevear, Judi; Wilshire, John F. K., Australian Journal of Chemistry, 1985, vol. 38, # 5, p. 723 - 733
  作者：Rosevear, Judi、Wilshire, John F. K.

  DOI：——

  日期：——