4,6-二硝基-1,3-苯二羰酰氯 | 1723-42-8

• 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: 4,6-二硝基-1,3-苯二羰酰氯
• 英文名称: 4,6-dinitroisophthaloyl chloride
• 英文别名: 4,6-Dinitro-1,3-benzenedicarbonyl chloride；4,6-dinitrobenzene-1,3-dicarbonyl chloride
• CAS: 1723-42-8
• 化学式: C₈H₂Cl₂N₂O₆
• 分子量: 293.02
• InChiKey: BVJAHSGPQFJMLI-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  419.5±40.0 °C(Predicted)
• 密度：
  1.765±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-二硝基-1,3-苯二羰酰氯 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4,6-bis((naphthalen-2-ylamino)methyl)benzene-1,3-diamine
  参考文献：
  名称：

  Overcoming Regioselectivity Issues Inherent in Bis-Tröger's Base Preparation

  摘要：

  [GRAPHICS]Bis-Troger's base derivatives are a new family of molecular tweezers. A major drawback to their study is a lack of commercially available precursors, ortho-nitrocarboxylic acids. A reverse synthetic strategy starting from known dinitrodicarboxylic acids, which circumvents this problem, is presented. Via this methodology regioisomeric bis-TB derivatives can be prepared selectively, using only common aromatic amines that are typically commercially available.

  DOI：

  10.1021/ol061913m
• 作为产物：
  描述：

  4,6-二硝基-1,3-二甲苯 在 chromium(VI) oxide 、 氯化亚砜 、 硫酸 作用下， 生成 4,6-二硝基-1,3-苯二羰酰氯
  参考文献：
  名称：

  Aromatic Oligoureas:  Enforced Folding and Assisted Cyclization

  摘要：

  Aromatic oligoureas are forced into well-defined conformation by incorporated intramolecular hydrogen bonds. Shape-persistent tetraureas macrocycles were obtained in a one-step [2 + 2] reaction in good yields.

  DOI：

  10.1021/ol0526322

文献信息

• CHEMISTRY OF NYBOMYCIN: II. SYNTHESIS OF 4,5-DIMETHYL-2,7-DIOXO-1,2,7,8-TETRAHYDRO-1,8-DIAZAANTHRACENE
  作者：Graham Leadbetter、Kenneth L. Rinehart Jr.

  DOI：10.1139/v65-214

  日期：1965.5.1

  4,5-Dimethyl-2,7-dioxo-1,2,7,8-tetrahydro-1,8-diazaanthracene, a compound previously obtained from phosphorus – hydrogen iodide reduction of deoxynybomycin, has been synthesized in eight steps from m-xylene, in 5% overall yield.

  4,5-二甲基-2,7-二氧-1,2,7,8-四氢-1,8-二氮蒽，是一种先前通过脱氧尼波霉素的磷-氢碘还原得到的化合物，经过八个步骤从间二甲苯合成，总产率为5%。
• Über 4,6-Dinitro-isophtalsäure und einige Kondensationsprodukte aus Dinitro-xylol und Dinitro-toluol mit Aldehyden (16. Mitteilung über Isatogene und Indole)
  作者：Paul Ruggli、Otto Schmid

  DOI：10.1002/hlca.19350180131

  日期：——
• Über 4,6-Diamino-1,3-diacetyl-benzol und seine Überführung in Derivate des lin. Benzo-dipyridins. (30. Mitteilung über Stickstoff-Heterocyclen)
  作者：Paul Ruggli、Heinrich Reichwein

  DOI：10.1002/hlca.193702001130

  日期：——
• Chiral Amino Acid Recognition by a Porphyrin-Based Artificial Receptor
  作者：Yasuhisa Kuroda、Yusuke Kato、Takuji Higashioji、Jun-ya Hasegawa、Shinichi Kawanami、Masatoshi Takahashi、Nobuyuki Shiraishi、Kazuhito Tanabe、Hisanobu Ogoshi

  DOI：10.1021/ja00149a018

  日期：1995.11

  Molecular recognition of amino acid methyl esters by doubly bridged porphyrin Zn complexes was investigated. A chiral, bridged porphyrin was prepared from the alpha,alpha,alpha,alpha-atropisomer of meso-tetrakis(o-aminophenyl)porphyrin and 4-nitroisophthaloyl chloride. The similar reactions using unsubstituted isophthaloyl, 5-nitroisophthaloyl, and 4,6-dinitroisophthaloyl chlorides as the bridging reagents gave corresponding nonchiral bridged porphyrins. The Zn complex of the chiral porphyrin exhibits significant chiral recognition toward amino acids. For example, the chiral receptor porphyrin shows D-/L-selectivity of 7.5 for valine methyl ester at 293 K in CH2Cl2. Comparison of binding behavior of four types of bridged porphyrin Zn complexes and H-1 NMR investigations reveal that the present chiral recognition observed for amino acid methyl esters is caused by favorable hydrogen bond formation between the carbonyl group of the guest and the 3-carboxyamide of the 4-nitroisophthalic bridging benzene. Thermodynamic parameters of the present complexation were also determined, and two types of very strong linear isoequilibrium relationships between the observed entropies and enthalpies were found. One is the linear correlation (R = 0.993) between Delta H and T Delta S values observed for host-guest combinations of bridged porphyrins-amino acid esters, and another is that (R = 0.997) observed for combinations of tetraphenylporphyrin-amino acid esters and bridged porphyrins-3-amino-2,4-dimethylpentane. The very large slopes observed for these linear correlations indicate that the significant amount of the conformational freedom of the guests is lost even during the process of simple coordination without hydrogen bond formation.
• Aromatic Oligoureas:  Enforced Folding and Assisted Cyclization
  作者：Aimin Zhang、Yaohua Han、Kazuhiro Yamato、Xiao Cheng Zeng、Bing Gong

  DOI：10.1021/ol0526322

  日期：2006.3.2

  Aromatic oligoureas are forced into well-defined conformation by incorporated intramolecular hydrogen bonds. Shape-persistent tetraureas macrocycles were obtained in a one-step [2 + 2] reaction in good yields.