N-亚硝基-N-乙基脲 | 759-73-9

• 物质功能分类: 化学试剂 - 有机试剂 - 脲
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 中文名称: N-亚硝基-N-乙基脲
• 中文别名: 1-乙基-1-亚硝基脲；亚硝基乙基脲
• 英文名称: 1-ethyl-1-nitrosourea
• 英文别名: N-Ethyl-N-nitrosourea
• CAS: 759-73-9
• 化学式: C₃H₇N₃O₂
• mdl: MFCD00053635
• 分子量: 117.107
• InChiKey: FUSGACRLAFQQRL-UHFFFAOYSA-N

物化性质

• 熔点：
  103-1040C (dec)
• 沸点：
  182℃
• 密度：
  1.35
• 闪点：
  64℃
• 溶解度：
  DMSO（可溶）、甲醇（少量）
• 物理描述：
  N-nitroso-n-ethylurea appears as yellow-pink crystals or off-white powder. Sensitive to light.
• 颜色/状态：
  Very pale pink crystalline solid
• 蒸汽压力：
  2.0X10-2 mm Hg at 25 °C (est)
• 稳定性/保质期：
  Decomposes to diazoethane in alkaline solutions; stability in aqueous solutions is pH-dependent (20 °C) ... . Sensitive to humidity and light and should be refrigerated for storage.
• 分解：
  Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx).

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

在体外用标有(14)C的ENU对牛肝tRNA进行乙基化反应时，主要产物是1,7-二乙基鸟嘌呤。...经过体内乙基化后，从大鼠肝tRNA中分离出的主要反应产物是7-乙基鸟嘌呤和一个含有1,7-二乙基鸟嘌呤衍生物的类似嘧啶核苷酸的组分，其中imidazole环被打开。

In the ethylation of tRNA from calf liver with (14)C-labeled ENU in vitro, 1,7-diethylguanine was obtained as the main product. ... After in vivo ethylation, the main reaction product isolated from rat liver tRNA was 7-ethylguanine and a pyrimidine nucleotide-like fraction containing a 1,7-diethylguanine derivative with an opened imidazole ring.

来源:Hazardous Substances Data Bank (HSDB)

代谢

NEU是一种直接烷基化剂，已经证明可以在体外和体内对核酸进行乙基化。在大鼠体内给药NEU后，已在组织中检测到7-乙基鸟嘌呤、06-乙基鸟嘌呤、3-乙基腺嘌呤、7-乙基腺嘌呤和乙基磷酸三酯。06-乙基鸟嘌呤从大脑（靶器官）DNA中的丢失速度远低于从肝脏DNA中的丢失速度，而其他乙基化产物的丢失速度没有观察到这样的差异。

NEU is a direct alkylating agent and has been shown to ethylate nucleic acids both in vitro and in vivo. 7-Ethylguanine, 06-ethylguanine, 3-ethyladenine and 7-ethyladenine and ethylphosphate triesters have been detected in rat tissues after administration of NEU in vivo. 06-Ethylguanine was lost from DNA of brain (a target organ) much more slowly than from liver DNA, whereas no such difference was observed for the rate of loss of the other ethylated products.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别与用途：N-亚硝基-N-乙基脲（NEU）是一种固体。它被实验性地用作诱变剂，并在实验室合成重氮乙烷时作为乙基化剂。诱变效应已进行研究，以促进各种植物的生长。人体研究：用NEU处理培养的人类成纤维细胞，诱发了染色单体和染色体畸变。研究了NEU对培养血液淋巴细胞人类染色体的影响。在体外，人淋巴细胞的单个染色单体和等染色单体断裂、交换和多重断裂的发病率与剂量相关，剂量范围为25-200微克/毫升。O6-烷基鸟嘌呤-DNA烷基转移酶和核苷酸切除修复在保护人类细胞免受NEU的毒性和诱变影响方面发挥着重要作用。动物研究：给予大鼠单次口服剂量的NEU为10、20、40或80毫克/千克体重，在大脑、脊髓和周围神经系统中诱发了75/80动物的恶性神经母细胞瘤。即使在最低剂量，也有23/26的大鼠死于神经母细胞瘤（21例脑肿瘤）。在最高剂量下，9/16的大鼠患有肾母细胞瘤。在给予39只大鼠每周5天，连续52周饮用60毫克NEU/升的水中，观察到以下肿瘤：7个胃肿瘤（3个乳头状瘤，1个鳞状细胞癌和3个肉瘤，全部为雄性），9个大肠肿瘤（6个腺癌和3个肉瘤，全部为雄性），9个乳腺腺癌（8只为雌性，1只为雄性）和12个粒细胞性白血病。在出生至16周龄期间口服给予100毫克/千克体重NEU的单次或分次剂量的负鼠（Didelphis virginiana Kerr）中，发现了眼睛、肝脏、大脑、肾脏、肌肉和下颌的多种上皮和间充质胚胎性肿瘤（包括眼睛的神经外胚层肿瘤和肾母细胞瘤），这些肿瘤与人类婴儿的肿瘤非常相似。单日龄小鼠单次皮下注射NEU，剂量水平从10-160毫克/千克体重，发展出高肿瘤发病率。每月腹腔注射10毫克/动物的NEU，持续3个月，导致3/10的成年大鼠发生胸腺淋巴瘤。每月治疗5个月，用10毫克/动物，产生了9/20的胸腺淋巴瘤大鼠和5只其他髓系白血病。当30毫克/千克体重的NEU通过静脉注射给予叙利亚金仓鼠怀孕第15天时，14/22的后代发展出肿瘤，主要是神经系统肿瘤（5个三叉神经肿瘤和11个周围神经肿瘤）。没有观察到大脑或脊髓肿瘤。在活体大鼠胚胎和体外使用整体胚胎培养技术中，研究了NEU对颅面部发育的致畸作用。在怀孕大鼠的第9.5天给予单次腹腔注射NEU，诱导了多种颅面部畸形。除了形态缺陷外，还诱导了雄性小鼠在交配前用NEU处理后代的功能性缺陷（呼吸窘迫）。NEU在鼠伤寒沙门氏菌、大肠杆菌、低等和高等植物、果蝇和其他生物体中诱发突变。在暴露于4-5毫克NEU的果蝇中，观察到85%的X连锁隐性致死和可见突变。

IDENTIFICATION AND USE: N-Nitroso-N-ethylurea (NEU) is a solid. It is used experimentally as mutagen, and as ethylating agent in the laboratory synthesis of diazoethane. Mutagenic effect has been studied for promoting growth of various plants. HUMAN STUDIES: Treatment of cultured human fibroblasts with NEU induced both chromatid and chromosome aberrations. The effect of NEU on human chromosomes from cultured blood lymphocytes was studied. The incidence of single chromatid and isochromatid breaks, exchanges and multiple breaks in human lymphocytes in vitro was dose-dependent, at doses ranging 25-200 ug/mL. Both O6-alkylguanine-DNA alkyltransferase and nucleotide excision repair play an important role in protecting human cells from the toxic and mutagenic effects of NEU. ANIMAL STUDIES: Rats were given single oral doses of 10, 20, 40 or 80 mg/kg bw NEU, and malignant neurogenic tumors were induced in the brain, spinal cord and peripheral nervous system in 75/80 animals. Even at the lowest dose, 23/26 animals died with neurogenic tumors (21 with brain tumors). At the highest dose, 9/16 rats had nephroblastomas. Among 39 rats given 60 mg NEU/L of drinking-water on 5 days/week for 52 weeks, the following tumors were observed: 7 tumors of the stomach (3 papillomas, 1 squamous-cell carcinoma and 3 sarcomas, all in males), 9 tumors of the large intestine (6 adenocarcinomas and 3 sarcomas, all in males), 9 adenocarcinomas of the mammary gland (8 in females and 1 in a male) and 12 myelocytic leukemias were observed. A variety of epithelial and mesenchymal embryonal neoplasms of the eye, liver, brain, kidney, muscle and jaw (including neuroectodermal tumors of the eye and nephroblastomas), closely analogous to tumors of human infancy, were found in opossums (Didelphis virginiana Kerr) treated orally from birth to 16 weeks of age with 100 mg/kg bw NEU in either single or split doses. One-day-old mice given single s.c. injections of NEU at dose levels ranging from 10-160 mg/kg bw developed a high incidence of tumors. Monthly i.p. injections of 10 mg/animal NEU for 3 months caused thymic lymphomas in 3/10 adult rats. Monthly treatment with 10 mg/animal for 5 months produced thymic lymphomas in 9/20 treated rats and myeloid leukemias in 5 others. When 30 mg/kg bw NEU were given by i.v. injection to Syrian golden hamsters on day 15 of pregnancy, 14/22 offspring developed tumors, mainly of the nervous system (5 tumors the trigeminal nerve and 11 tumors of the peripheral nerves). No tumors of the brain or spinal cord were observed. Teratogenic effects of NEU on craniofacial development were investigated in rat embryos in vivo, and in vitro using a whole-embryo culture technique. A single intraperitoneal injection of NEU into the pregnant rat on day 9.5 of gestation induced several types of craniofacial malformations. A functional defect (respiratory distress), in addition to morphological defects, was induced in the offspring of male mice treated with NEU before mating. NEU Induces mutations in Salmonella typhimurium, Escherichia coli, lower and higher plants, in Drosophila melanogaster and in other organisms. A mutation yield of 85% X-linked recessive lethal and visible mutations was seen in Drosophila exposed to 4-5 mg NEU.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

N-亚硝基-N-乙基脲合理地被预期为人类致癌物，基于实验动物研究中充分的致癌性证据。

N-Nitroso-N-ethylurea is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据可用。在动物中有足够的致癌性证据。总体评估：2A组：该物质可能对人类致癌。

No data are available in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2A: The agent is probably carcinogenic to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌剂：N-乙基-N-亚硝基脲

IARC Carcinogenic Agent:N-Ethyl-N-nitrosourea

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2A组：可能对人类致癌

IARC Carcinogenic Classes:Group 2A: Probably carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

NEU在静脉注射后迅速从血液中消失，其半衰期为5-6分钟。NEU的高化学反应性使得酶催化不太可能参与其分解。

NEU was rapidly lost from the blood after its i.v. injection, with a half-life of 5-6 minutes. The high chemical reactivity of NEU renders it unlikely that enzymic catalysis is involved in its decomposition.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

N-[(14)C]乙基-N-亚硝脲在小鼠体内的组织分布和命运已经进行了研究。发现大部分注射的N-[(14)C]乙基-N-亚硝脲放射性以(14)CO2形式被呼出。全身自动放射性显影显示，在N-[(14)C]乙基-N-亚硝脲给药后不久，大多数组织中放射性分布均匀，这可能是由于均匀分布的物质和非酶促形成的乙基碳正离子与组织反应。血脑屏障似乎有能力部分阻止物质进入中枢神经系统。在肝脏中观察到高放射性，这可能意味着N-[(14)C]乙基-N-亚硝脲在该组织中通过酶促分解。观察到的肾脏标记可能与尿液中放射性排泄有关。肝脏和肾脏中的放射性在较晚的存活间隔内降低，并出现了一种分布模式，该模式以富含蛋白质或类固醇合成的组织和含脂肪的组织的标记为特征。分布模式与[(14)C]乙醛给药后观察到的分布模式一致，这可能是由于2碳池中正常生物合成整合放射性的结果。使用吡唑、尼亚拉胺和二乙基二硫代氨基甲酸盐预处理显著抑制了(14)CO2的呼出和肝脏中放射性的整合。这种效应可能是针对N-[(14)C]乙基-N-亚硝脲本身的分解，但也可能影响形成的2碳片段的代谢。预处理对其他组织中放射性的整合没有影响。

The tissue-disposition and fate of N-[(14)C]ethyl-N-nitrosourea has been studied in mice. A large part of the injected N-[(14)C]ethyl-N-nitrosourea radioactivity was found to be exhaled as (14)CO2. Whole-body autoradiography showed evenly distributed radioactivity in most tissues shortly after the administration of N-[(14)C]ethyl-N-nitrosourea which probably is due to the homogeneously distributed substance and the non-enzymatically formed ethyl-carbonium ions which have reacted with the tissues. The blood-brain barrier seemed to have a capacity to partially prevent the uptake of the substance in the central nervous system. A high radioactivity was observed in the liver, which may imply that N-[(14)C]ethyl-N-nitrosourea is enzymatically decomposed in this tissue. An observed labelling of kidneys may be connected with urinary excretion of radioactivity. The radioactivity in the liver and kidney decreased at later survival intervals and a distribution pattern appeared, which was characterized by a labelling of tissues with a high protein or steroid synthesis and of fat containing tissues. The distribution pattern corresponded to the one seen after the administration of [(14)C]acetaldehyde and is probably due to normal biosynthetic incorporation of radioactivity in the 2-carbon pool. Pretreatments with pyrazole, nialamide and diethyldithiocarbamate caused a marked inhibition of the exhalation of (14)CO2 and of the incorporation of radioactivity in the liver. This effect may be directed towards the decomposition of N-[(14)C]ethyl-N-nitrosourea itself, but an effect on the metabolism of formed 2-carbon fragments is also possible. The incorporation of radioactivity in other tissues was not influenced by the pretreatments.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险类别码：
  R20/21/22,R45,R46,R61
• 海关编码：
  2924199090
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 储存条件：
  -20°C

制备方法与用途

N-Nitroso-N-ethylurea is a precursor to diazoethane and possesses alkylating, carcinogenic, and mutagenic properties.

反应信息

• 作为反应物：
  描述：

  N-亚硝基-N-乙基脲 在 potassium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 0.25h， 生成 重氮乙烷
  参考文献：
  名称：

  重氮烷烷对钯催化的烯基硅烷的环丙烷化作用：Pd0机理的证据

  摘要：

  Pd 0 可以解决问题！链烯基硅烷可以在低Pd负载下被重氮烷烃有效地环丙烷化（请参见方案）。给出了该反应涉及Pd 0静止状态的明确证据。

  DOI：

  10.1002/chem.200802052
• 作为产物：
  描述：

  Cytochrome鎐frompigeonbreastmuscle 在 硫酸 、 sodium nitrite 作用下， 生成 N-亚硝基-N-乙基脲
  参考文献：
  名称：

  六元磺胺类药物与重氮甲烷的无金属扩环反应：七元烯磺酰胺的一种方法

  摘要：

  已开发了由N-甲苯磺酰hydr原位生成的六元N-磺酰亚胺碱与不稳定的重氮甲烷的新的无金属环扩环反应。该反应通过Tiffeneau–Demjanov重排和分子内质子转移互变异构过程提供了有价值的七元烯磺酰胺。而且，该扩环反应可以单锅方式进行，并通过使用芳基醛将其规模扩大至克级，而无需分离N-甲苯磺酰hydr。

  DOI：

  10.1002/anie.201508804

文献信息

• 7-Methyl- and 7-phenylcyclohepta-1, 3, 5-trienes from benzvalene via 3, 3a, 4, 5, 6, 6a-hexahydro-4, 5, 6-methenocyclopentapyrazoles and tetracyclo[4. 1. 0. 0.0] heptanes
  作者：Manfred Christl、Erich Brunn、Wolfgang R. Roth、Hans-Werner Lennartz

  DOI：10.1016/s0040-4020(01)80119-8

  日期：1989.1

  norbornene with both diazoalkanes cannot be rationalized on the basis of frontier orbital energies. On direct photolysis, the pyrazolines 2a-g were converted into the tetracyclo[4. 1. 0. 02,4. 03,5] heptanes 4a-g exclusively. These compounds gave the 1, 3, 5-cycloheptatrienes 5a, b, d, e, g in high yields on treatment with silver ions, thus providing better access to 7, 7-dimethyl-(5d) and 7, 7-diphenylcycloheptatriene

  向重氮甲烷，重氮乙烷，2-重氮丙烷，苯基重氮甲烷和二苯基重氮甲烷中添加苯并戊烯（1）以良好的收率得到1-吡唑啉2a-g。通过竞争实验，已经确定了苯并戊烯（1）和降冰片烯相对于重氮甲烷和2-重氮丙烷的相对反应性。苯并戊烯与两种重氮烷烃的反应速度约为降冰片烯的两倍，这不能基于前沿轨道能量来合理化。直接光解后，吡唑啉2a-g转化为四环[4]。1. 0. 0 2,4。0 3,5 ]庚烷4a-g只。在用银离子处理后，这些化合物可高收率地产生1，3，5-环庚烯5a，b，d，e，g，从而提供了更好的7、7-二甲基-（5d）和7,7-二苯基环庚三烯（5克）。出人意料的是，后一种化合物与大量的正十八碳烯形式处于平衡状态。-已经确定了4a至5a重排的反应热，这可以导出四环[4]的形成热。1. 0. 0 2,4。0 3,5 ]庚烷（4a）。
• ³H-labelled alkyl-nucleotides, -nucleosides and -bases for the immunoanalytical quantification of DNA damage and repair
  作者：Wolfgang Drosdziok、Catrin Lutze、Kai Krüger、Karl-Heinz Glüsenkamp、Manfred F. Rajewsky

  DOI：10.1002/jlcr.721

  日期：2003.8

  Analysis of the formation and repair of structurally modified DNA is of particular interest in the study of carcinogenesis, cancer therapy and aging. The quantification of specific DNA lesions by sensitive immunoanalytical methods requires radiotracers with high specific activity. We describe the synthesis of 3H-labelled adenine-, cytosine-, guanine- and thymine-alkyl derivatives by nucleophilic N- and O-alkylation using alkyl halides and diazoalkanes: 3-alkyl-[8-3H]adenine (Alkyl = Me, Et, n-Bu); O6-alkyl-deoxy[1′,2′-3H]guanosine (Alkyl = Me, Et, i-Pro, n-Bu); O6-ethyl-deoxyguanosine-5′-triphosphate ([2-3H-Ethyl]; [8-3H]); O6-alkyl-9-hydroxyhexyl-[8-3H] guanine (Alkyl=Me, Et); 7-ethyl-[8,5′-3H]guanosine-3′,5′-cyclic-phosphate; O2-andO4-alkyl-[methyl, 1′,2′-3H]thymidine (Alkyl=Me, Et); the conversion of 3H-labelled thymidine to the corresponding 5-methylcytidine; the synthesis of three different 8-oxo-guanine tracers; and the generation of thymidine glycol (5,6-dihydroxy-5,6-dihydro-[methyl-3H]thymidine) from thymidine. All radiotracers were sucessfully employed in competitive radioimmunoassays for the quantification of defined DNA alkylation products in DNA repair analyses. Copyright © 2003 John Wiley & Sons, Ltd.

  结构修饰DNA的形成与修复分析，在癌变、癌症治疗和衰老的研究中具有特殊意义。灵敏的免疫分析法测定特定DNA损伤需要高比活性的放射性示踪剂。我们描述了使用烷基卤和重氮烷通过亲核N-和O-烷基化合成3H标记的腺嘌呤、胞嘧啶、鸟嘌呤和胸腺嘧啶的烷基衍生物：3-烷基-[8-3H]腺嘌呤（烷基=甲基、乙基、正丁基）；O6-烷基-脱氧[1′,2′-3H]鸟苷（烷基=甲基、乙基、异丙基、正丁基）；O6-乙基-脱氧鸟苷-5′-三磷酸（[2-3H-乙基]；[8-3H]）；O6-烷基-9-羟基己基-[8-3H]鸟嘌呤（烷基=甲基、乙基）；7-乙基-[8,5′-3H]鸟苷-3′,5′-环磷酸酯；O2和O4-烷基-[甲基, 1′,2′-3H]胸苷（烷基=甲基、乙基）；将3H标记的胸苷转化为相应的5-甲基胞苷；三种不同8-氧代鸟嘌呤示踪剂的合成；以及从胸苷生成胸苷乙二醇（5,6-二羟基-5,6-二氢-[甲基-3H]胸苷）。所有放射性示踪剂均成功用于竞争性放射免疫分析，以量化DNA修复分析中的特定DNA烷基化产物。版权所有 © 2003 John Wiley & Sons, Ltd.
• Enantiospecific first total synthesis of (6S,7R)-silphiperfolan-6-ol
  作者：A. Srikrishna、Gopalasetty Nagaraju、Vishal M. Sheth

  DOI：10.1016/j.tet.2012.01.063

  日期：2012.3

  Enantiospecific first total synthesis of the angular triquinane sesquiterpene (6S,7R)-silphiperfolan-6-ol has been accomplished, starting from 2-(3-isopropenyl-2-methylene-1-methylcyclopent-1-yl)acetic acid (readily available from (R)-limonene) employing an efficient, regioselective intramolecular rhodium carbenoid insertion into the CH bond of a tertiary methyl group as the key step.

  对映体特异性的角triquinane倍半萜烯（6第一全合成小号，7 - [R）-silphiperfolan -6-醇已经完成，从2-（3-异丙烯基-2-亚甲基-1-甲基环戊-1-基）乙酸（原料可以很容易地从（R）-柠檬烯中获得），其方法是将有效的区域选择性分子内铑类胡萝卜素插入叔甲基的CH键中，这是关键步骤。
• Organocatalysed Asymmetric β-Amination and Multicomponentsyn-Selective Diamination of α,β-Unsaturated Aldehydes
  作者：Hao Jiang、Johanne B. Nielsen、Martin Nielsen、Karl Anker Jørgensen

  DOI：10.1002/chem.200700696

  日期：2007.11.5

  3-aminoaldehydes in good yields and enantioselectivities. This is followed by two easy transformations giving rise to optically active 1,3-aminoalcohols, a common motif in many biologically active compounds, for example, fibrinogen receptor antagonists. Furthermore, optically active alpha,beta-syn-diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one-pot reaction.

  提出了一种简单且可负担的途径，该途径通过使用有机催化来获得手性β-氨基化和α，β-氨基化的醛，1,3-氨基醇及相关化合物。手性仲胺（S）-2- [双（3,5-双三氟甲基苯基）三甲基硅烷基氧基甲基]吡咯烷用作催化剂来活化α，β-不饱和醛，从而使琥珀酰亚胺可以添加1,4-区域-和-立体选择性的方式，从而以良好的产率和对映选择性形成N-保护的1，3-氨基醛。随后是两个简单的转化，产生了光学活性的1,3-氨基醇，这是许多生物活性化合物（例如，纤维蛋白原受体拮抗剂）中的常见基序。此外，光学活性Alpha
• Steric effect in alkylation reactions by<i>N</i>-alkyl-<i>N</i>-nitrosoureas: a kinetic approach
  作者：J. A. Manso、M. T. Pérez-Prior、M. P. García-Santos、E. Calle、J. Casado

  DOI：10.1002/poc.1402

  日期：2008.11

  by five N-alkyl-N-nitrosoureas (methyl-, ethyl-, propyl-, butyl-, and allylnitrosourea) were investigated in 7:3 (v/v) water/dioxane medium in the 5.0–6.5 pH range. Decomposition of alkylnitrosoureas (ANU) gives rise to alkyldiazonium ions that yield NBP-R adducts directly or through carbocations in certain instances. The NBP alkylation rate constants by these species were determined. The following sequence

  4-（对硝基苄基）吡啶（NBP）的烷基化反应是通过五个N-烷基-N进行的，该陷阱是具有类似于DNA碱基的亲核特性的烷基化剂-亚硝基脲（甲基，乙基，丙基，丁基和烯丙基亚硝基脲）在7：3（v / v）水/二恶烷介质中于5.0-6.5 pH范围内进行了研究。烷基亚硝基脲（ANU）的分解产生烷基重氮离子，在某些情况下可直接或通过碳阳离子产生NBP-R加合物。确定了这些物种的NBP烷基化速率常数。发现以下烷基化电位序列：甲基->乙基->烯丙基->丙基->丁基。将Ingold-Taft相关分析应用于动力学结果表明，NBP烷基化反应主要通过空间控制发生。NBP-R加合物的摩尔吸收系数的值还揭示了空间效应对烷基化加合物形成的决定性影响。动力学结果与ANU的生物学活性一致。版权所有©2008 John Wiley＆Sons，Ltd.

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