1,3,5,7-cubanetetracarbonyl chloride | 161980-55-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,3,5,7-cubanetetracarbonyl chloride
• 英文别名: cubane-1,3,5,7-tetracarbonyl tetrachloride；Cubane-1,3,5,7-tetracarbonyl chloride
• CAS: 161980-55-8
• 化学式: C₁₂H₄Cl₄O₄
• 分子量: 353.973
• InChiKey: LSJJLPOBMQGLPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3,5,7-cubanetetracarbonyl chloride 在 叠氮基三甲基硅烷 、 2,6-di-tert-butylpyridine dihydrochloride 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 Cubane-1,3,5,7-tetracarbonyl tetraazide
  参考文献：
  名称：

  1,3,5,7-四硝基立方烷的合成和化学，包括酸度测量、邻硝基阴离子的形成以及五硝基立方烷和六硝基立方烷的初步制备1

  摘要：

  立方烷交替角上的硝基增强了立方氢的酸度（pKa~21），并为准备好的阴离子形成提供足够的活化。1,3,5,7-四硝基立方烷的钠盐很容易与亲电子试剂反应，从而产生更高取代度的立方烷，如甲氧基-和（三甲基甲硅烷基）四硝基立方烷。这些物种的阴离子也很容易形成，可用于进一步取代立方核。四氧化二氮与四硝基立方烷的阴离子反应生成 1,2,3,5,7-五硝基立方烷，这是第一个含有邻位硝基的立方烷。该反应可能涉及将阴离子氧化为相应的自由基。同样，五硝基立方烷的阴离子用于制备 1,2,3,4,5,7-六硝基立方烷，这是迄今为止制造的硝化程度最高的立方烷。

  DOI：

  10.1021/ja970552q
• 作为产物：
  描述：

  cubane-1,3,5,7-tetracarboxylic acid 在 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 1,3,5,7-cubanetetracarbonyl chloride
  参考文献：
  名称：

  Systematic substitution on the cubane nucleus. Synthesis and properties of 1,3,5-trinitrocubane and 1,3,5,7-tetranitrocubane

  摘要：

  A systematic methodology is developed for the synthesis of highly symmetric, polysubstituted cubanes. The synthesis of cubanes with C3v and T(d) symmetry is achieved. Details are given for the preparation of 1,3,5-trinitrocubane and 1,3,5,7-tetranitrocubane, compounds of interest as superior high-energy, shock-insensitive explosives. The structures of these new materials, determined by single-crystal X-ray analysis, are discussed in detail. DSC analysis of their thermal decomposition is presented. The effect of nitro groups on the C-13-NMR spectra of cubanes is noted.

  DOI：

  10.1021/ja00075a039

文献信息

• Polyazido compounds
  申请人：Dave Paritosh R.

  公开号：US06841690B1

  公开（公告）日：2005-01-11

  This invention relates to a series of novel compounds having the general structures A and B: including 2-azido-2-azidomethyl-1,3-diazidopropane (1), 2-azidomethyl-2-hydroxy-1,3-diazidopropane (2), 2-azidomethyl-2-nitrato-1,3-diazidopropane (3), 2-azidomethyl-2-nitro-1,3-diazidopropane (4), 2,2-dinitro-1,3-diazidopropane (5), methallyidiazide (6), a dimer of methallyidiazide (6), comprising 3a,8a-Bis-azidomethyl-3a,4,8a,9-tetrahydro-3H,8H-bis[1,2,3]triazolo[1,5-a;1″,5″-d]pyrazine (6-Dimer), 1,3-diazidoacetone (7), and 2-Oximido-1,3-diazidopropane (8). Also shown are reaction intermediates of these compounds, including 2,2-bis(chloromethyl)oxirane (9), and 2,2-bis(azidomethyl)oxirane (10). In addition, a number of potentially useful energetic compounds have been prepared from the low molecular weight polyazido compounds above, including N-2(azido-1-azidomethyl-ethylidene)-N″-(2,4-dinitrophenyl)-hydrazine (7-DNPH), 1,3-Bis(4-carboxytriazolyl)2,2-dinitropropane (12), Tris(4-carboxytriazolomethyl)methanol (13), Benzene-1,3,5-tricarboxylic acid tris(2-azido-1,1-bisazidomethyl-ethyl)ester (14), Adamantane 1,3,5,7-tetracarboxylic acid tetrakis(2-azido-1,1-bisazidomethyl-ethyl)ester (15), Adamantane carboxylic acid 2-azido-1,1-bisazidomethyl-ethyl)ester (16), cubane 1,3,5,7-tetracarboxylic acid tetrakis (2-azido-1,1-bisazidomethyl-ethyl)ester (17), cubane 1,4-dicarboxylic acid bis(2-azido-1,1-bisazidomethyl-ethyl)ester (18).

  本发明涉及一系列新型化合物，其一般结构为A和B，包括2-叠氮基-2-叠氮甲基-1,3-叠氮丙烷（1）、2-叠氮甲基-2-羟基-1,3-叠氮丙烷（2）、2-叠氮甲基-2-硝酸酯-1,3-叠氮丙烷（3）、2-叠氮甲基-2-硝基-1,3-叠氮丙烷（4）、2,2-二硝基-1,3-叠氮丙烷（5）、甲烯基叠氮基（6）、甲烯基叠氮基的二聚体（6-Dimer）、1,3-叠氮丙酮（7）和2-肟基-1,3-叠氮丙烷（8）。此外，还显示了这些化合物的反应中间体，包括2,2-双(氯甲基)环氧烷（9）和2,2-双(叠氮甲基)环氧烷（10）。此外，还从上述低分子量多叠氮化合物中制备了许多潜在有用的高能化合物，包括N-2（叠氮-1-叠氮甲基-乙烯）-N″-（2,4-二硝基苯基）-肼（7-DNPH）、1,3-叠氮基-2,2-二硝基丙烷-4-羧酸三唑（12）、三（4-羧酸三唑甲基）甲醇（13）、苯-1,3,5-三羧酸三（2-叠氮基-1,1-叠氮甲基-乙基）酯（14）、立方烷-1,3,5,7-四羧酸四（2-叠氮基-1,1-叠氮甲基-乙基）酯（15）、立方烷羧酸2-叠氮基-1,1-叠氮甲基-乙基酯（16）、立方烷-1,3,5,7-四羧酸四（2-叠氮基-1,1-叠氮甲基-乙基）酯（17）和立方烷-1,4-二羧酸双（2-叠氮基-1,1-叠氮甲基-乙基）酯（18）。
• Glycoluril core molecules for combinatorial libraries
  申请人：Rebek Julius

  公开号：US20050250830A1

  公开（公告）日：2005-11-10

  The present invention provides novel glycoluril derivatives for use as core molecules in combinatorial chemistry. Core molecules of the present invention can contain from one to six building blocks. Preferred building blocks are substituted amine radicals. Combinatorial libraries containing such core molecules are also provided.

  本发明提供了可用作组合化学核心分子的新型甘氨酰脲衍生物。本发明的核心分子可包含一至六个结构单元。优选的结构单元是取代的胺基。本发明还提供了含有此类核心分子的组合库。
• Photochemical Functionalization of Cubanes
  作者：A. Bashir-Hashemi、J. Li、Nathan Gelber、Herman Ammon

  DOI：10.1021/jo00108a037

  日期：1995.2

  A wide range of cubanecarboxylic acids has been prepared by a simple and efficient photochemical process. Chlorocarbonylation of cubanecarboxylic acid with oxalyl chloride under UV irradiation produced polysubstituted cubanes with chlorocarbonyl groups predominantly on the remote sites (beta or gamma). The T-d-tetraacid chloride 6b, in which chlorocarbonyl groups are in alternate positions, was the major product. Irradiation of 1,2,3,7-tetrasubstituted cubane 9 with oxalyl chloride gave pentasubstituted cubane 10. Other isomers, 1,3,5,7-tetrasubstituted cubane 6 and 1,2,4,7-tetrasubstituted cubane 8, in which chlorocarbonylation would occur at positions ortho to three or two carbonyl groups, gave only chlorinated products. Photochemical reaction of oxalyl chloride with nitrocubanes gave chlorocarbonylated and chlorinated nitrocubanes. Ab initio calculations show carbon-hydrogen bond strength at different positions of the cubane is not the major factor in determining the regioselectivity of the chlorocarbonylation. A polar effect might be the key factor in site selectivity.
• Preparation of ‘cage molecule’ based polyazido core units for dendrimer synthesis
  作者：Paritosh R. Dave、Raja Duddu、Kathy Yang、Reddy Damavarapu、Nathaniel Gelber、Rao Surapaneni、Richard Gilardi

  DOI：10.1016/j.tetlet.2004.01.037

  日期：2004.3

  Core Molecules based on benzene-, cubane-, adamantane-polycarboxlates with peripheral polyazido substitution are reported. The first synthesis of 1.3-diazidoacetone and its conversion to the corresponding oxime, DNPH, and 2,2-dinitro derivatives is also reported. (C) 2004 Elsevier Ltd. All rights reserved.
• US6939973B1
  申请人：——

  公开号：US6939973B1

  公开（公告）日：2005-09-06