CN109180703A - 7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物 - Google Patents

7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物 Download PDF

Info

Publication number
CN109180703A
CN109180703A CN201810896786.8A CN201810896786A CN109180703A CN 109180703 A CN109180703 A CN 109180703A CN 201810896786 A CN201810896786 A CN 201810896786A CN 109180703 A CN109180703 A CN 109180703A
Authority
CN
China
Prior art keywords
furazano
furoxans
hydroxyl
double
azepine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201810896786.8A
Other languages
English (en)
Other versions
CN109180703B (zh
Inventor
翟连杰
毕福强
王伯周
吴敏杰
李祥志
周群
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xian Modern Chemistry Research Institute
Original Assignee
Xian Modern Chemistry Research Institute
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xian Modern Chemistry Research Institute filed Critical Xian Modern Chemistry Research Institute
Priority to CN201810896786.8A priority Critical patent/CN109180703B/zh
Publication of CN109180703A publication Critical patent/CN109180703A/zh
Application granted granted Critical
Publication of CN109180703B publication Critical patent/CN109180703B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

本发明公开了一种7‑羟基双呋咱并氧化呋咱并氮杂环庚烯化合物，其结构式如(I)所示：

Description

7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物
技术领域
本发明涉及一种7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物，属于含能材料领域。
背景技术
氮杂芳环类含能化合物是目前含能材料研究领域的热点，包括吡唑、咪唑、三唑、四唑、噁二唑、三嗪及四嗪等，其中呋咱和氧化呋咱含能化合物因其能量密度高、热稳定性好、氧平衡高、生成焓大等优点而成为含能材料研究的热点之一，可用于高能炸药、高能氧化剂、低特征信号推进剂、气体发生剂、燃速调节剂、火焰配方抑制剂和烟火药等领域，成为构筑高能量密度材料优良母体。张海昊等人在《7-氨基三呋咱并[3,4-b:3′,4′-f:3″,4″-d]氮杂环庚烯合成、晶体结构及热行为》，火炸药学报，2014，37(4)，19-24一文中公开了7-氨基三呋咱并[3,4-b:3′,4′-f:3″,4″-d]氮杂环庚烯的结构、合成路线及该化合物的计算性能，其结构如(II)所示：
该化合物的密度为1.79g/cm3，氧平衡(ΩCO)为-27.3％，爆速7718m/s，爆压26Gpa，但是该化合物密度较小、氧平衡差、爆速和爆压较低。
发明内容
本发明所要解决的技术问题是克服背景技术的不足和缺陷，提供一种密度大、氧平衡好、爆速和爆压较高的7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物。
本发明的7-羟基双呋咱并氧化呋咱并氮杂环庚烯的合成路线：
以3,4-双(4′-硝基呋咱-3′-基)氧化呋咱为原料，与羟胺水溶液发生取代反应得到7-羟基双呋咱并氧化呋咱并氮杂环庚烯。
本发明的7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物，其结构式如(I)所示：
本发明的7-羟基双呋咱并氧化呋咱并氮杂环庚烯的合成方法，包括以下步骤：搅拌下，在温度-20℃～-5℃，将3,4-双(4′-硝基呋咱-3′-基)氧化呋咱加入到无水乙腈中，缓慢滴加质量分数为50％羟胺水溶液，反应30min～1h，反应完成后过滤得7-羟基双呋咱并氧化呋咱并氮杂环庚烯，其中，3,4-双(4′-硝基呋咱-3′-基)氧化呋咱与羟胺的摩尔比为1:2.5～4。
本发明的优点：
本发明的7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物密度较大，其密度为1.93g/cm3，对比文件的7-氨基三呋咱并[3,4-b:3′,4′-f:3″,4″-d]氮杂环庚烯的密度为1.79g/cm3；本发明的7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物氧平衡好，其氧平衡为-9.6％，对比文件的7-氨基三呋咱并[3,4-b:3′,4′-f:3″,4″-d]氮杂环庚烯的氧平衡为-27.3；本发明的7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物爆速和爆压较高，其爆速为8245m/s，爆压为32Gpa，对比文件的7-氨基三呋咱并[3,4-b:3′,4′-f:3″,4″-d]氮杂环庚烯的爆速和爆压分别为7718m/s和26Gpa。
具体实施方式
以下结合实施例对本发明作进一步详细说明。
以下是发明人给出的实施例，需要说明的是，这个实施例是较优的例子，主要用于理解本发明，但本发明不限于这个实施例。
实施例1
7-羟基双呋咱并氧化呋咱并氮杂环庚烯的合成
搅拌下，在温度-15℃下，将(4.5g,15mmol)3,4-双(4′-硝基呋咱-3′-基)氧化呋咱加入到无水30mL乙腈中，缓慢滴加(3.0g,45mmol)质量分数为50％羟胺水溶液，反应45min，过滤得7-羟基双呋咱并氧化呋咱并氮杂环庚烯1.8g，收率44.7％，纯度98.8％。
结构鉴定：
红外光谱：IR(KBr,cm-1),υ：3282,2087,2454,1658,1637,1608,1588,1555,1528,1482,1440,1395,1355,1173,1054,996,969,939,851,797,736；
核磁光谱：1H NMR(DMSO-d6,500MHz),δ：7.81；13C NMR(DMSO-d6,125MHz),δ：155.08,154.68,144.98,135.72,133.66,105.96；
元素分析：分子式C6HN7O5
理论值：C 28.70,H 0.40,N 39.04
实测值：C 28.31,H 0.45,N 38.64；
上述结构鉴定数据证实得到物质确实是7-羟基双呋咱并氧化呋咱并氮杂环庚烯。
本发明7-羟基双呋咱并氧化呋咱并氮杂环庚烯的性能
(1)物化性能
外观：黄色固体
溶解度：易溶于二甲基亚砜、N,N-二甲基甲酰胺、丙酮等，微溶于乙酸乙酯；不溶于石油醚、二氯甲烷；
密度：1.93g/cm3排惰性气体法；
氧平衡(ΩCO)：-9.6％。
(2)爆轰性能
爆速：密度为1.93g/cm3，计算爆速为8245m/s K-J方程
爆压：密度为1.93g/cm3，计算爆压为32Gpa K-J方程
本发明7-羟基双呋咱并氧化呋咱并氮杂环庚烯的用途
本发明的7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物具有密度大、氧平衡好、能量高等特点，可以作为高能炸药组分应用于炸药和火箭推进剂领域。

Claims (1)

1.一种7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物，其结构式如(I)所示：
CN201810896786.8A 2018-08-08 2018-08-08 7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物 Active CN109180703B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810896786.8A CN109180703B (zh) 2018-08-08 2018-08-08 7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810896786.8A CN109180703B (zh) 2018-08-08 2018-08-08 7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物

Publications (2)

Publication Number Publication Date
CN109180703A true CN109180703A (zh) 2019-01-11
CN109180703B CN109180703B (zh) 2021-07-27

Family

ID=64920582

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810896786.8A Active CN109180703B (zh) 2018-08-08 2018-08-08 7-羟基双呋咱并氧化呋咱并氮杂环庚烯化合物

Country Status (1)

Country Link
CN (1) CN109180703B (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109796469A (zh) * 2019-03-06 2019-05-24 西安近代化学研究所 7-(2,4,6-三硝基苯基)双呋咱并氧化呋咱并氮杂环庚三烯化合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2534989C1 (ru) * 2013-05-31 2014-12-10 Федеральное государственное унитарное предприятие "Специальное конструкторско-технологическое бюро "Технолог" ПРОИЗВОДНЫЕ 7H(7R)-ТРИС[1,2,5]ОКСАДИАЗОЛО[3,4-b:3',4'-d:3",4"-f]АЗЕПИНА И СПОСОБ ИХ ПОЛУЧЕНИЯ

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2534989C1 (ru) * 2013-05-31 2014-12-10 Федеральное государственное унитарное предприятие "Специальное конструкторско-технологическое бюро "Технолог" ПРОИЗВОДНЫЕ 7H(7R)-ТРИС[1,2,5]ОКСАДИАЗОЛО[3,4-b:3',4'-d:3",4"-f]АЗЕПИНА И СПОСОБ ИХ ПОЛУЧЕНИЯ

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
廉鹏，等: "三呋咱并氧(氮)杂环庚三烯的密度泛函理论研究", 《计算机与应用化学》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109796469A (zh) * 2019-03-06 2019-05-24 西安近代化学研究所 7-(2,4,6-三硝基苯基)双呋咱并氧化呋咱并氮杂环庚三烯化合物
CN109796469B (zh) * 2019-03-06 2021-08-20 西安近代化学研究所 7-(2,4,6-三硝基苯基)双呋咱并氧化呋咱并氮杂环庚三烯化合物

Also Published As

Publication number Publication date
CN109180703B (zh) 2021-07-27

Similar Documents

Publication Publication Date Title
Tang et al. Enforced planar FOX-7-like molecules: a strategy for thermally stable and insensitive π-conjugated energetic materials
Klapötke et al. Thermal stabilization of energetic materials by the aromatic nitrogen-rich 4, 4′, 5, 5′-tetraamino-3, 3′-bi-1, 2, 4-triazolium cation
Yin et al. Nitrogen-rich azoles as high density energy materials: reviewing the energetic footprints of heterocycles
Bian et al. 3-Nitro-1-(2 H-tetrazol-5-yl)-1 H-1, 2, 4-triazol-5-amine (HANTT) and its energetic salts: highly thermally stable energetic materials with low sensitivity
Gidaspov et al. Novel trinitroethanol derivatives: high energetic 2-(2, 2, 2-trinitroethoxy)-1, 3, 5-triazines
Wang et al. Synthesis of 1-(2 H-tetrazol-5-yl)-5-nitraminotetrazole and its derivatives from 5-aminotetrazole and cyanogen azide: a promising strategy towards the development of C–N linked bistetrazolate energetic materials
Manzoor et al. Nitro-tetrazole based high performing explosives: Recent overview of synthesis and energetic properties
Sun et al. Combination of four oxadiazole rings for the generation of energetic materials with high detonation performance, low sensitivity and excellent thermal stability
Lei et al. A facile strategy for synthesizing promising pyrazole-fused energetic compounds
Lei et al. New pyrazole energetic materials and their energetic salts: combining the dinitromethyl group with nitropyrazole
Sun et al. Dancing with 5-substituted monotetrazoles, oxygen-rich ions, and silver: towards primary explosives with positive oxygen balance and excellent energetic performance
Zhang et al. Towards improved explosives with a high performance: N-(3, 5-dinitro-1 H-pyrazol-4-yl)-1 H-tetrazol-5-amine and its salts
Gao et al. Recent progress in taming FOX-7 (1, 1-diamino-2, 2-dinitroethene)
Kumar et al. Asymmetric N, N′-ethylene-bridged azole-based compounds: Two way control of the energetic properties of compounds
Zhang et al. Insensitive Nitrogen‐Rich Materials Incorporating the Nitroguanidyl Functionality
Zhang et al. Combining 5, 6-fused triazolo-triazine with pyrazole: a novel energetic framework for heat-resistant explosive
Tang et al. Synthesis and characterization of 1, 1′-azobis (5-methyltetrazole)
Kumar et al. 3, 4, 5-Trinitro-1-(nitromethyl)-1 H-pyrazole (TNNMP): a perchlorate free high energy density oxidizer with high thermal stability
Cheng et al. A potential insensitive-highly-energetic material through conjugation-promoted N-oxidation strategy
Yan et al. Exploiting the energetic potential of 1, 2, 4-oxadiazole derivatives: combining the benefits of a 1, 2, 4-oxadiazole framework with various energetic functionalities
Ma et al. Formation of trinitromethyl functionalized 1, 2, 4-triazole-based energetic ionic salts and a zwitterionic salt directed by an intermolecular and intramolecular metathesis strategy
Liu et al. Synthesis, characterization and properties of nitrogen-rich compounds based on cyanuric acid: a promising design in the development of new energetic materials
Sun et al. Tetracyclic pyrazine-fused furazans as insensitive energetic materials: syntheses, structures, and properties
Xue et al. A family of energetic materials based on 1, 2, 4-oxadiazole and 1, 2, 5-oxadiazole backbones with low insensitivity and good detonation performance
Zhang et al. Synthesis and Properties of 3, 6‐Dinitropyrazolo [4, 3‐c]‐pyrazole (DNPP) Derivatives

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant