黑索金 | 121-82-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪烷类
• 中文名称: 黑索金
• 中文别名: 黑索今；1,3,5-三硝基六氢-1,3,5-三嗪；环三次甲基三硝胺；环三甲撑三硝胺；环三亚甲基三硝胺；钝化黑索金；黑索今(环三亚甲基三硝胺)；三亚甲基三硝胺；环三次甲基三硝铵
• 英文名称: 1,3,5-trinitro-1,3,5-triazinane
• 英文别名: Hexahydro-1,3,5-trinitro-1,3,5-triazine；RDX；hexogen；1,3,5-trinitroperhydro-1,3,5-triazine；cyclotrimethylenetrinitramine；Cyclonite
• CAS: 121-82-4
• 化学式: C₃H₆N₆O₆
• mdl: MFCD00458725
• 分子量: 222.117
• InChiKey: XTFIVUDBNACUBN-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  稳定性差，易爆炸。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  9

ADMET

代谢

杨树植株（Populus deltoides x nigra, DN34）在水培条件下生长，暴露于50毫克/升的六氢-1,3,5-三硝基-1,3,5-三唑烷（RDX）24小时。通过逆转录酶（RT）实时PCR分析了可能参与有毒炸药代谢的基因表达。研究的基因是通过参考先前在大肠杆菌中通过暴露于2,4,6-三硝基甲苯（TNT）而上调的相应基因来选择的... 研究的目标基因包括几个编码已知参与异生物质污染解毒的酶的基因，如谷胱甘肽S-转移酶（GSTs）、细胞色素P-450s（CYPs）、NADPH依赖性还原酶和过氧化物酶。从拟南芥TNT可诱导基因出发，从JGI杨树基因组项目数据库中检索相应的杨树序列，并用于设计基因特异性引物。18S核糖体DNA（rDNA）用作内部标准，记录的基因表达水平通过与未暴露植物的参考进行归一化。在三个独立的实验中，发现五种基因在叶组织中通过暴露于RDX显著扩增，包括GST（9.7倍）、CYP（1.6倍）、还原酶（1.6-1.7倍）和过氧化物酶（1.7倍）。在根组织中，只有一个GST基因通过暴露于RDX显著扩增（2.0倍）。这些结果首次表明，杨树植株暴露于RDX会导致几种可能参与炸药解毒的基因的诱导。

Poplar plants (Populus deltoides x nigra, DN34) growing under hydroponic conditions were exposed to 50 mg /per/ L of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) for 24 hr. The expression of genes potentially involved in the metabolism of toxic explosives was analyzed by reverse-transcriptase (RT) real-time PCR. Genes under study were selected by reference to corresponding genes that were previously shown to be upregulated in the model plant Arabidopsis thaliana by exposure to 2,4,6-trinitrotoluene (TNT)... The target genes investigated include several genes encoding for enzymes known to be involved in the detoxification of xenobiotic pollutants, such as glutathione S-transferases (GSTs), cytochrome P-450s (CYPs), NADPH-dependent reductases, and peroxidases. Starting from A. thaliana TNT-inducible genes, corresponding Populus sequences were retrieved from the JGI Poplar Genome Project database and were used to design gene-specific primers. 18S ribosomal DNA (rDNA) was used as an internal standard and recorded gene expression levels were normalized by reference to nonexposed plants. In three separate experiments, five genes were found to be significantly amplified in leaf tissues by exposure to RDX, including GST (9.7 fold), CYP (1.6 fold), reductases (1.6-1.7 fold), and peroxidase (1.7 fold). In root tissues, only a single GST gene was found to be significantly amplified by exposure to RDX (2.0 fold). These results show, for the first time, that the exposure of poplar plants to RDX results in the induction of several genes that are potentially involved in explosive detoxification.

来源:Hazardous Substances Data Bank (HSDB)

代谢

该研究检查了Yucatan小型猪（公猪和母猪）单次口服灌胃5毫升/千克（14）C标记的六氢-1,3,5-三硝基-1,3,5-三嗪（RDX）后的代谢情况（43毫克/千克，56微居里/千克，溶于0.5%羧甲基纤维素中）。在给予剂量后的1、6、12和24小时选择了收集血液、尿液和粪便的时间点。在给药后24小时，收集了肝脏样本。血液、血浆、肝脏和排泄物中分析了总RDX衍生放射性，并鉴定了代谢物。尿液通过液相色谱-质谱（LC/MS）分析，确定了两种环裂解代谢物，4-硝基-2,4-二氮杂丁醛和4-硝基-2,4-二氮杂丁酰胺，以及母体RDX的量化水平。更灵敏的方法（LC/MS/MS）分析还显示，尿液中有微量的RDX代谢物1-亚硝基-3,5-二硝基-1,3,5-三嗪环己烷（MNX）（公猪和母猪）和1-硝基-3,5-二亚硝基-1,3,5-三嗪环己烷（DNX）（公猪）。血浆的LC/MS/MS分析也揭示了RDX的量化水平以及MNX、DNX和1,3,5-三亚硝基-1,3,5-三嗪环己烷（TNX）的微量水平。所有肝脏提取物均未显示RDX或任何可识别代谢物的量化水平。大部分放射性以水溶性高分子量化合物的形式存在。口服给予猪的RDX通过失去两个硝基团然后发生环裂解而迅速代谢。

The study ... examined the metabolism of (14)C-labeled hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) resulting from a single oral gavage of 5 mL/kg to male and female Yucatan miniature pigs (43 mg/kg, 56 microCi/kg in 0.5% carboxymethylcellulose in water). Blood, urine, and feces were collected at selected times of 1, 6, 12, and 24 hr post dose. At 24 hr post dose, liver samples were collected. Blood, plasma, liver, and excreta were analyzed for total RDX-derived radioactivity and metabolites were identified. ... Analysis of urine by liquid chromatography-mass spectrometry (LC/MS) identified quantifiable levels of two ring-cleavage metabolites, 4-nitro-2,4-diazabutanal and 4-nitro-2,4-diaza-butanamide, as well as parent RDX. ... Analysis by a more sensitive method (LC/MS/MS) also showed trace amounts of the RDX metabolites 1-nitroso-3,5-dinitro-1,3,5-triazacyclohexane (MNX) (in both male and female urine) and 1-nitro-3,5-dinitroso-1,3,5-triazacyclohexane (DNX) (in male urine). Analysis of plasma by LC/MS/MS also revealed quantifiable levels of RDX and trace levels of MNX, DNX, and 1,3,5-trinitroso-1,3,5-triazacyclohexane (TNX). None of the liver extracts showed quantifiable levels of RDX or any identifiable metabolites. Most of the radioactivity was in the form of water-soluble high-molecular-weight compounds. RDX when given orally to pigs was rapidly metabolized by loss of two nitro groups followed by ring cleavage.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Sprague-Dawley 大鼠，无论雌雄（体重 200-250 克），通过灌胃给予未标记或放射性碳-14标记的RDX，剂量为每天 20 毫克/千克，持续最多 90 天，或者自由接触未标记的 RDX 或放射性碳-14标记的 RDX 饱和饮水（50-70 微克/毫升）最多 90 天。大部分标记物以呼出的放射性碳-14二氧化碳和尿液中未识别的代谢物形式排出。

Sprague-Dawley rats of both sexes (200-250 g) were either dosed with unlabeled or (14)C-RDX by gavage at 20 mg/kg/day for up to 90 days or allowed free access to unlabeled RDX or (14)C-RDX-saturated drinking water (50-70 ug/mL) for up to 90 days. The majority of the label was excreted as exhaled (14)C-carbon dioxide and as unidentified metabolites in the urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

兔肝细胞色素P450 2B4催化了黑索金（RDX）向4-硝基-2,4-二唑丁醛的生物转化。兔肝细胞色素P450 2B4和Rhodococcus sp. DN22菌株的完整细胞均催化了每个反应的RDX分子释放两个亚硝酸盐离子。对细胞色素P450 2B4和Rhodococcus sp. DN22菌株的比较研究表明，在产物分布和细胞色素P450抑制剂抑制作用方面存在显著相似性。

...A cytochrome P450 2B4 from rabbit liver catalyzed a biotransformation of RDX to 4-nitro-2,4-diazabutanal. Both the cytochrome P450 2B4 and intact cells of Rhodococcus sp. strain DN22 catalyzed the release of two nitrite ions from each reacted RDX molecule. A comparative study of cytochrome P450 2B4 and Rhodococcus sp. strain DN22 revealed substantial similarities in the product distribution and inhibition by cytochrome P450 inhibitors.

来源:Hazardous Substances Data Bank (HSDB)

代谢

关于经吸入、口服或皮肤接触后人体内RDX代谢物的研究尚未见报道。一些研究报告称，通过细胞色素P450的生物转化，RDX可以产生4-硝基-2,4-二氮杂丁醛和亚硝酸盐离子。有限的毒理学数据表明，RDX可以通过胃肠系统、肺和皮肤吸收，并分布到脑脊液、血浆、尿液和粪便中。RDX将在几天内通过呼吸和尿液排出体外。(L259,A162)

There are no studies available regarding RDX metabolites in humans following inhalation, oral, or dermal exposure. Some studies reported that 4-nitro-2,4-diazabutanal, and nitrite ions are produced through biotransformation of RDX by cytochrome P450. The limited toxicological data show that RDX is absorbed through the gastrointestinal system, lungs, and skin, and is distributed to the cerebrospinal fluid, plasma, urine, and feces. RDX will leaves the body in the breath and urine within a few days. (L259,A162)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

RDX可以通过吸入燃烧RDX的烟雾或吸入RDX粉末的尘埃进入肺部。它也可以通过摄入受污染的水进入人体。它还可能通过皮肤进入血液或通过皮肤的切口或破损处进入。它还阻断电子传递。（第10节，第259行）

RDX can get into the lungs after breathing in the fumes of burning RDX or breathing in the dust from powdered RDX. It can also enter the body after ingestion of contaminated water. It may also pass through the skin into the bloodstream or enter through cuts or breaks in the skin. It also blocks electron transport. (T10, L259)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

分类：C；可能的人类致癌物。分类依据：雌性B6C3F1小鼠的肝细胞腺瘤和癌。人类致癌性数据：无。

CLASSIFICATION: C; possible human carcinogen. BASIS FOR CLASSIFICATION: Hepatocellular adenomas and carcinomas in female B6C3F1 mice. HUMAN CARCINOGENICITY DATA: None.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A4；不可归类为人类致癌物。

A4; Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

RDX 可导致癫痫发作。吸入 RDX 可能会导致胃肠道、血液学、肝脏和肾脏的影响。

RDX can cause seizures. Inhalation exposure to RDX can lead to gastrointestinal, hematological, hepatic, and renal effects. (L259)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

这项研究检查了Yucatan小型猪（公母各半）单次口服给予含有(14)C标记的六氢-1,3,5-三硝基-1,3,5-三嗪（RDX）的剂量后其代谢情况。剂量为5毫升/千克体重，相当于43毫克/千克和56微居里/千克，溶解在0.5%羧甲基纤维素的水溶液中。在给予剂量后的1、6、12和24小时收集血液、尿液和粪便样本。在给药后24小时收集肝脏样本。血液、血浆、肝脏和排泄物中分析了总RDX衍生的放射性活性和代谢物。尿液是雄性和雌性消除(14)C-RDX派生的放射性的主要途径。胃肠道内容和粪便中的放射性水平相对较低，这表明口服剂量后(14)C-RDX几乎被完全吸收。

The study ... examined the metabolism of (14)C-labeled hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) resulting from a single oral gavage of 5 mL/kg to male and female Yucatan miniature pigs (43 mg/kg, 56 uCi/kg in 0.5% carboxymethylcellulose in water). Blood, urine, and feces were collected at selected times of 1, 6, 12, and 24 hr post dose. At 24 hr post dose, liver samples were collected. Blood, plasma, liver, and excreta were analyzed for total RDX-derived radioactivity and metabolites were identified. Urine was the major route of elimination of (14)C-RDX-derived radioactivity in both males and females. Relatively low levels of radioactivity were found in gastrointestinal contents and in feces, suggesting nearly complete absorption of (14)C-RDX following an oral dose. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

...（14）C-RDX派生的放射活性的毒物动力学在给予单次口服剂量后进行了检测，该剂量是以0.1%羧甲基纤维素水悬浮液的形式配制的，目标剂量水平为43毫克/千克...给雄性和雌性尤卡坦小型猪。在给药后1、6、12和24小时从每只动物收集血液。通过24小时后给药收集尿液和粪便。...尿液是消除（14）C-RDX派生的放射活性的主要途径，雄性和雌性分别占放射性剂量的17.3%和17.6%。RDX吸收良好。粪便占给药剂量的不到1%，胃肠道内容物约占剂量的5.6%。收集的所有组织中都观察到（14）C-RDX派生的放射活性的广泛分布。放射性活性的最高浓度在肝脏和肾脏中观察到。计算出的放射性剂量百分比在肝脏（3.5至5.8%）和肌肉（2.5至4.7%）中较高。

... The toxicokinetics of (14)C-RDX-derived radioactivity was examined following administration of a single oral dose formulated as an aqueous suspension in 0.1% carboxymethylcellulose at a target dose level of 43 mg/kg ... to male and female Yucatan mini pigs. Blood was collected at 1, 6, 12 and 24 hr post dose from each animal. Urine and feces were collected through 24 hr post dose. ... Urine was the major route for elimination of (14)C-RDX-derived radioactivity, with 17.3 and 17.6% of the radioactive dose, respectively, in males and females. RDX was well absorbed. Feces accounted for less than 1% of administered dose and gastrointestinal contents for about 5.6% of the dose. The distribution of (14)C-RDX derived radioactivity was extensive, with radioactivity observed in all collected tissues. The highest concentrations of radioactivity were observed in liver and kidney. The calculated percent of radioactive dose was high in liver (3.5 to 5.8%) and muscle (2.5 to 4.7%).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

它从胃和肺逐渐吸收，但没有证据表明可以通过皮肤吸收。

It is slowly absorbed from the stomach and apparently from the lungs, but there is no evidence of skin absorption.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

Sprague-Dawley 大鼠（200-250克）无论雌雄，通过灌胃给予未标记的RDX或（14）C-RDX，剂量为20毫克/千克/天，最长持续90天，或者自由接触未标记的RDX或（14）C-RDX饱和的饮用水（50-70微克/毫升），最长持续90天。RDX没有在任何被检查的组织中积累，也没有迹象表明随着重复给药，大鼠血浆中的RDX会持续增加。在90天的饮用水研究中，每天恢复的（14）C标记物，在1、4、8和13周结束时估计，在54%到89%之间变化。大部分标记物以呼出的（14）-二氧化碳和尿液中未识别的代谢物形式排出。

Sprague-Dawley rats of both sexes (200-250 g) were either dosed with unlabeled or (14)C-RDX by gavage at 20 mg/kg/day for up to 90 days or allowed free access to unlabeled RDX or (14)C-RDX-saturated drinking water (50-70 ug/mL) for up to 90 days. RDX did not accumulate in any tissue examined nor were there any tendencies for plasma RDX to increase continuously with repeated dosing in rats. In the 90-day drinking water study the daily recovery of the (14)C label, estimated at the end of 1, 4, 8, and 13 wk, varied between 54 and 89%. The majority of the label was excreted as exhaled (14)-carbon dioxide and as unidentified metabolites in the urine.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  黑索金的毒性虽小于TNT但仍具有毒性，吸入后可导致中毒，误服会引起头晕、恶心、呕吐、流涎及多汗等症状，严重者会出现抽搐。它富含铅，因此对环境有严重的污染风险。储存时应远离火源和热源，并与起爆器材、碱类等分开存放。严禁混储混运，避免震动、撞击和摩擦，防止扬尘。

制备方法与用途

黑索今制备

1. 伍尔维次法：以硝酸（100%）及六亚甲基四胺（乌洛托品）为原料，其中硝酸的用量是六亚甲基四胺的11倍。反应温度需控制在30℃以下。反应过程中，六亚甲基四胺会经由硝解作用生成RDX、NH₃及甲醛。

2. 兹贝雷-奚斯勒-罗斯法：将甲醛和硝酸铵加入乙酸酐中，反应温度控制在70℃左右。此方法需要大量乙酸酐且收率较低，因此并不理想。

3. 巴克曼法：结合伍尔维次法和兹贝雷-奚斯勒-罗斯法而成的组合法。其原料包括六亚甲基四胺、硝酸铵、硝酸及乙酸酐。巴克曼法的产率约为80%，所得RDX熔点约190℃，其中含有约10%的HMX。由于此方法使用醋酸酐和硝酸较少，且产率较高，从而降低了黑索今的成本。

4. 沃尔夫拉姆法：甲醛与氨基磺酸钾反应生成亚甲基氨基磺酸钾。该环状化合物通过80%发烟硝酸及20%三氧化硫进行硝化后可得到RDX。此方法的产率约为80%～90%。 用途：可用作高能炸药。 用途：也可用作民爆炸药。

反应信息

• 作为反应物：
  描述：

  黑索金 生成 乙烯酮
  参考文献：
  名称：

  固体1,3,5-Trinitro-1,3,5-Triazinane（RDX）的红外多光子离解中的难以捉摸的Ketene（H2 CCO）通道。

  摘要：

  对1,3,5-三硝基-1,3,5-三氮杂烷（RDX）分解所涉及的基本机理的理解仍然是高能材料和物理（有机）化学社区面临的主要挑战，主要是因为存在多个竞争的解离通道可能涉及到这些产物，并且以前的产物检测方法对异构体没有选择性。在这项研究中，我们利用微秒脉冲红外激光在温和条件下在5 K下分解RDX薄膜，以限制碎片通道。使用异构体选择性单光电离飞行时间质谱（PI‐ReTOF‐MS）检测程序升温脱附阶段中的升华分解产物。该技术使我们能够将m / z = 42的产物信号分配给烯酮（H 2CCO），但不是先前推测的重氮甲烷（H 2 CNN； 42 amu）。电子结构计算支持我们的实验观察，并揭示了RDX通过异乎寻常的四元环中间体最终导致难以捉摸的烯酮（H 2 CCO）的分解机理。这项研究强调了利用异构体选择性检测方案来探测基于硝胺的高能材料真正分解产物的必要性。

  DOI：

  10.1002/cphc.201901202
• 作为产物：
  描述：

  3,7-二乙酰基-1,3,5,7-四氮杂二环[3.3.1]壬烷 在 硝酸铵 、 copper(II) nitrate trihydrate 、 硝酸 、 乙酸酐 作用下， 反应 4.0h， 以62%的产率得到黑索金
  参考文献：
  名称：

  金属路易斯酸对[3,7-二乙酰-1,3,5,7-四氮杂双环（3.3.1）-壬烷]硝化作用的影响研究

  摘要：

  通过实验和理论方法研究了金属离子对DAPT [3,7-二乙酰基-1,3,5,7-四氮杂双环（3.3.1）壬烷]和HA（六胺）的硝化作用的影响。发现组合试剂M（NO - 3）n / Ac 2 / NH 4 NO 3（M = Mg 2 +，Cu 2 +，Pb 2 +，Bi 3+，Fe 3+和Zr 4+）在DAPT硝化实验中非常有效。用1检测到DAPT硝化过程中的关键中间体1 H NMR。提出并分析了中间体的形成机理。基于硬-软和酸碱原理以及离子络合物的稳定能量，解释了由不同的金属硝酸盐催化的DAPT和HA硝化的一些不同结果。从视后一点，一些阳离子具有高极化配体，例如，OSO。2 CF 3 - ，（CF 3 SO 2）2 Ñ - ，和（C 4 ˚F 9 SO 2）2 Ñ - ，可以增加产率。两种新设计的催化剂Cu [（CF 3 SO 2）测试了2 N] 2和Cu [（C 4 F 9 SO 2）2

  DOI：

  10.1002/cjoc.201190079
• 作为试剂：
  描述：

  N,N-二甲基苯胺 在 黑索金 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 N-甲基对硝基苯胺 、 N,N-二甲基对硝基苯胺
  参考文献：
  名称：

  通过硝基酯和硝胺的光解裂解检测爆炸物

  摘要：

  含有硝胺的炸药 RDX 和含有硝基酯的炸药 PETN 被证明在暴露于阳光下时容易发生光致碎裂。含有硝基酯和硝胺部分的模型化合物也显示在暴露于紫外线照射时会碎裂。这种光裂解的产物是反应性的、亲电子的 NO x物质，例如亚硝酸和硝酸、一氧化氮和二氧化氮。N , N -二甲基苯胺能够被RDX 和 PETN的反应性亲电子 NO x光裂解产物硝化。一系列 9,9-二取代的 9,10-二氢吖啶 (DHAs) 由N-苯基邻氨基苯甲酸甲酯或二苯胺衍生物，同样显示出被 RDX 和 PETN 的光致碎裂产物快速硝化。由于荧光供体-受体发色团的产生，在 DHA 硝化时观察到 550 nm 处的新（开启）发射信号。使用荧光光谱法，约的存在。1.2 ng 的 RDX 和 320 pg 的 PETN 可以通过暴露在阳光下的固态 DHA 指示剂检测到。RDX 和 PETN 的光致碎裂产物对芳香胺的硝化是一种独特的、高度

  DOI：

  10.1021/jo200280c

文献信息

• A Convenient Method For<i>N</i>-Nitration Using Ammonium Nitrate/Trifluoroacetic Anhydride
  作者：Suresh Chander Suri、Robert D. Chapman

  DOI：10.1055/s-1988-27696

  日期：——

  A mixture of ammonium nitrate and trifluoroacetic anhydride is found to be a convenient reagent for N-nitration in the synthesis of nitramines, nitramides, and nitrimides. Yields are comparable to those from conventional, but less convenient or safe, nitrating reagents.

  发现硝酸铵和三氟乙酸酐的混合物是一种方便的N-硝化试剂，用于合成硝胺、硝酰胺和硝酰亚胺。其产率与传统但更不方便或安全的硝化试剂相当。
• Application of [PVI-SO₃H]NO₃ as a novel polymeric nitrating agent with ionic tags in preparation of high-energetic materials
  作者：Hassan Sepehrmansourie、Mahmoud Zarei、Mohammad Ali Zolfigol、Amin Mehrzad、Hamid Reza Hafizi-Atabak

  DOI：10.1039/d1ra00651g

  日期：——

  In this paper, poly(vinyl imidazole) sulfonic acid nitrate [PVI-SO3H]NO3 awas synthesized and fully characterized. Then, it was used for the preparation of energetic materials.

  本文合成并充分表征了聚(乙烯基咪唑)磺酸硝酸盐[PVI-SO3H]NO3。然后，它被用于制备含能材料。
• Nitrolysis of syn,syn-2,4,6-tris-(n-propyl)-hexahydro-1,3,5-tripropionyl-s-triazine
  作者：Matthew C. Davis、Gregory H. Imler

  DOI：10.1016/j.tetlet.2020.152665

  日期：2020.12

  5-tripropionyl-s-triazine (3) with 1,1,1-trifluoroacetyl nitrate (TFAN) generated in situ from 1,1,1-trifluoroacetic anhydride and nitric acid in nitromethane gave mononitramine, dinitramine and trinitramine products depending on reaction duration and concentration of TFAN. Each of the three new nitramine products was purified and characterized by multi-nuclear magnetic resonance spectroscopy. An X-ray structure for

  顺式的硝解，顺式-2,4,6-三- （ñ -丙基） -六氢-1,3,5- tripropionyl-小号嗪（3（TFAN）产生）与1,1,1-三氟乙酰基硝酸盐在由1,1,1-三氟乙酸酐和硝酸在硝基甲烷中原位产生单硝胺，二硝胺和三硝胺产物，具体取决于反应持续时间和TFAN的浓度。三种新的硝胺产品均已纯化，并通过多核磁共振波谱进行了表征。报道了syn，syn -2,4,6-tris-（n -propyl）-hexahydro -1,3,5-trinitro- s -triazine（syn，syn - 10）的X射线结构。异构体syn，anti– 3 在这些硝解条件下未产生类似的硝胺产物。
• 15N Studies of the Mechanisms of Nitration of Hexamethylenetetramine and 3,7-Diacetyl-1,3,5,7-tetraazabicyclo[3.3.1]nonane
  作者：Michael R. Crampton、Michael Jones、John K. Scranage、Peter Golding

  DOI：10.1016/s0040-4020(01)86730-2

  日期：1988.1

  the nitration of 3,7-diacetyl-1,3,5,7-tetraazabicyclo(3.3.1]nonane (DAPT) to 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DADN) involves selective cleavage of the methylene bridge. A synthesis of DADN by acetolysis of DPT is reported.

  报道了对六甲基四氢呋喃（1）及其某些衍生物进行硝化的机理研究，并将其与乙酰化反应进行了比较。使用[ 15 N 4 ]-和[ 14 N 4的混合物，与硝酸进行硝化反应质谱测定产物中的[-]-化合物和氮同位素的目的地。结果表明，在硝化（1）中得到3,7-二硝基-1,3,5,7-四氮杂双环[3.3.1]壬烷（DPT）发生了广泛的环裂解，得到了包含单个氨基氮片段的物质。但是将3,7-二乙酰基1,3,5,7-四氮杂双环（3.3.1）壬烷（DAPT）硝化为1,5-二乙酰基-3,7-二硝基-1,3,5,7-四氮杂环辛烷（DADN）涉及亚甲基桥的选择性裂解，报道了通过DPT的乙酰化合成DADN。
• Alkaline Decomposition of Cyclic Nitramines
  作者：S. G. Il’yasov、A. A. Lobanova

  DOI：10.1007/s11176-005-0181-6

  日期：2005.1

  Treatment of 1,3,5-trinitro-1,3,5-triazacyclohexane and 1,3,5,7-tetranitro-1,3,5,7-tetrazacyclo-octane with potassium hydroxide gives dipotassium salt of methylenedinitramine.

  用氢氧化钾处理1,3,5-三硝基-1,3,5-三氮杂环己烷和1,3,5,7-四硝基-1,3,5,7-四氮杂环辛烷得到甲基化二乙胺的二钾盐。

表征谱图