2-羟基-1,2-双(2-硝基苯基)乙酮 | 59163-44-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-羟基-1,2-双(2-硝基苯基)乙酮
• 英文名称: 2,2'-dinitrobenzoin
• 英文别名: 2-hydroxy-1,2-bis(2-nitrophenyl)ethanone
• CAS: 59163-44-9
• 化学式: C₁₄H₁₀N₂O₆
• 分子量: 302.243
• InChiKey: IAAMYWQVCIFESD-UHFFFAOYSA-N

物化性质

• 熔点：
  155.5 °C
• 沸点：
  545.8±40.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  123.58
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-羟基-1,2-双(2-硝基苯基)乙酮 在 dimethyl sulfide borane 、 对甲苯磺酸一水合物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,2-bis(2-nitrophenyl)-2-[(7,8,8-trimethyloctahydro-4,7-methanobenzo[b]furan-2-yl)oxy]ethanol
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017
• 作为产物：
  描述：

  1,2-Bis-(2-nitro-phenyl)-2-trimethylsilanyloxy-ethanone 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-羟基-1,2-双(2-硝基苯基)乙酮
  参考文献：
  名称：

  Chiral linker. Part 3: Synthesis and evaluation of aryl substituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for the diastereoselective reduction of α-keto esters

  摘要：

  Five partly novel aryl substituted m-hydrobenzoins were synthesized and the corresponding desymmetrized hydrobenzoin ethers evaluated as open chain chiral auxiliaries in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates, resulting in de values of up to 91%. Two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliary in the same type of reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.017

文献信息

• Synthesis of DMSO–SbCl₅(1 : 1) Complex and Its Oxidizing Action toward Alcohols
  作者：Jiro Yamamoto、Satoshi Ito、Takashi Tsuboi、Toshiaki Tsuboi、Kumiko Tsukihara

  DOI：10.1246/bcsj.58.470

  日期：1985.2

  From an equimolar mixture of DMSO and SbCl5 in carbon tetrachloride, a DMSO–SbCl5(1 : 1) complex (1) was formed as a white precipitate in a quantitative yield. The structure of 1 was determined by X-ray crystallographic analysis. Butyraldehydes, para-substituted benzaldehydes and benzils were obtained by the oxidation of butylalcohols, para-substituted benzylalcohols and benzoins using 1 as an oxidizing agent.

  在四氯化碳中加入等摩尔的二甲基亚砜（DMSO）和氯化锑（SbCl5）混合物后，生成了二甲基亚砜-氯化锑（SbCl5）（1:1）复合物（1），呈白色沉淀，收率极高。通过 X 射线晶体分析确定了 1 的结构。以 1 为氧化剂，通过氧化丁基醇、对位取代的苄基醇和安息香，得到了丁醛、对位取代的苄基醛和苯甲酰苯。
• Catalytically active lead(<scp>ii</scp>)–imidazolium coordination assemblies with diversified lead(<scp>ii</scp>) coordination geometries
  作者：Chatla Naga Babu、Paladugu Suresh、Katam Srinivas、Arruri Sathyanarayana、Natarajan Sampath、Ganesan Prabusankar

  DOI：10.1039/c5dt04409j

  日期：——

  derived from the reaction between the corresponding flexible, semi flexible or rigid imidazolium carboxylic acid ligands and lead nitrate. The imidazolium linker present in these molecules likely plays a triple role such as the counter ion to balance the metal charge, the ligand being an integral part of the final product and the catalyst facilitating carbon–carbon bond formation reaction. These lead–imidazolium

  通过相应的柔性，半柔性或刚性咪唑羧酸配体与硝酸铅之间的反应得到了五个具有新颖结构图案的Pb（II）-咪唑羧酸酯配位体。这些分子中存在的咪唑连接基可能起着三重作用，例如平衡金属电荷的抗衡离子，配体是最终产物的组成部分，并且催化剂促进碳-碳键形成反应。这些铅-咪唑鎓配位化合物具有可变的化学和热稳定性以及催化活性。这些新制备的催化剂对苯偶姻缩合反应具有很高的活性，并具有良好的官能团耐受性。
• Misra, Pranati; Mohapatra, R. C.; Khandual, N. C., Journal of the Indian Chemical Society, 1986, vol. 63, p. 291 - 294
  作者：Misra, Pranati、Mohapatra, R. C.、Khandual, N. C.

  DOI：——

  日期：——
• Safari, Javad; Arani, Naimeh Moshtael; Isfahani, Anousheh Ramezan, Asian Journal of Chemistry, 2011, vol. 23, # 2, p. 495 - 498
  作者：Safari, Javad、Arani, Naimeh Moshtael、Isfahani, Anousheh Ramezan

  DOI：——

  日期：——