N-亚硝基-N-(甲酰基甲基)丁胺 | 70625-90-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-亚硝基-N-(甲酰基甲基)丁胺
• 英文名称: N-Butylethanalnitrosamine
• 英文别名: N-nitroso-N-(formylmethyl)butylamine；N-Butyl-nitrosamino-N-acetaldehyd；(Butylnitrosoamino)acetaldehyde；N-butyl-N-(2-oxoethyl)nitrous amide
• CAS: 70625-90-0
• 化学式: C₆H₁₂N₂O₂
• 分子量: 144.173
• InChiKey: YBZFKQXWWAOFFD-UHFFFAOYSA-N

物化性质

• 沸点：
  256.6±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-亚硝基-N-(甲酰基甲基)丁胺 以 乙酸甲酯 、 乙腈 为溶剂， 反应 1.0h， 生成 C₁₂H₁₅N₇O₆
  参考文献：
  名称：

  Characterization of directly acting mutagens produced from N-nitroso-N-(formylmethyl)alkylamines: Their possible involvement in the carcinogenesis of N-nitrosamines having a 2-hydroxyethyl group.

  摘要：

  从 N-亚硝基-N-（甲酰基甲基）烷基胺（3）中分离出直接作用的诱变剂，并确定其为 N-亚硝基-N-烷基-1-羟基亚氨基-2-氧代乙胺（4）。根据核磁共振波谱阐明了它们的结构，并通过衍生成结晶的 2，4-二硝基苯肼（5）得到了证实。化合物 4（烷基=乙基和丁基）对鼠伤寒沙门氏菌 TA 1535 和大肠杆菌 WP2 hcr- 具有强烈的致突变性，而带有叔丁基的 4 则没有致突变性。4 的形成被认为是通过 3 的亚硝基化进行的，这表明带有 2-羟乙基的 N-亚硝胺可能参与了甲酰基甲基代谢物的致癌过程。

  DOI：

  10.1248/cpb.35.4022
• 作为产物：
  描述：

  n-butylaminoacetaldehyde diethyl acetale 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 N-亚硝基-N-(甲酰基甲基)丁胺
  参考文献：
  名称：

  Suzuki,E.; Okada,M., Chemical and pharmaceutical bulletin, 1979, vol. 27, p. 541 - 544

  摘要：

  DOI：

文献信息

• In Vitro DNA Deamination by α-Nitrosaminoaldehydes Determined by GC/MS-SIM Quantitation
  作者：Misun Park、Richard N. Loeppky

  DOI：10.1021/tx990126d

  日期：2000.2.1

  The deamination of DNA bases by three alpha-nitrosaminoaldehydes, butylethanalnitrosamine, methylethanalnitrosamine, and N-nitroso-2-hydroxymorpholine (NHMOR), the direct metabolite of potent animal carcinogen N-nitrosodiethanolamine, was demonstrated by a set of in vitro experiments. The deamination of guanine, adenine, and cytosine bases in nucleotides, oligonucleotides, and calf thymus DNA gave xanthine, hypoxanthine, and uracil, respectively. The order of relative reactivities of the bases was as listed above. Deamination of cytosine to uracil was detected by the reaction of P-32-labeled oligonucleotide ([5'-P-32]CGAT) followed by enzymatic hydrolysis. Quantitative analysis of deamination of guanine and adenine in calf thymus DNA was performed by a gas chromatography/mass spectrometry-selected ion monitoring method. Both the extent and the rate of the deamination reactions which occur by transnitrosation from the alpha-nitrosaminoaldehyde to the base were determined for formation of xanthine and hypoxanthine. The deamination of guanine by NHMOR remained significant at low substrate levels.
• SUZUKI, EMAKO;OSABE, MARIKO;MOCHIZUKI, MASATAKA;WAKABAYASHI, YUOK;OKADA, +, CHEM. AND PHARM. BULL., 35,(1987) N 10, 4022-4030
  作者：SUZUKI, EMAKO、OSABE, MARIKO、MOCHIZUKI, MASATAKA、WAKABAYASHI, YUOK、OKADA, +

  DOI：——

  日期：——
• Characterization of directly acting mutagens produced from N-nitroso-N-(formylmethyl)alkylamines: Their possible involvement in the carcinogenesis of N-nitrosamines having a 2-hydroxyethyl group.
  作者：EMAKO SUZUKI、MARIKO OSABE、MASATAKA MOCHIZUKI、YUKO WAKABAYASHI、MASASHI OKADA

  DOI：10.1248/cpb.35.4022

  日期：——

  Directly acting mutagens formed from N-nitroso-N- (formylmethyl) alkylamines (3) were isolated and identified as N-nitroso-N-alkyl-1-hydroxyimino-2-oxoethylamines (4). Their structures were elucidated on the basis of nuclear magnetic resonance spectra and confirmed by derivatization to the crystalline 2, 4-dinitrophenylhydrazones (5). Compounds 4 (alkyl =ethyl and butyl) were strongly mutagenic to Salmonella typhimurium TA 1535 and Escherichia coli WP2 hcr- without metabolic activation, while 4 with a tert-butyl group was not mutagenic. The formation of 4 is considered to proceed by the nitrosation of 3, indicating a possible involvement of the formylmethyl metabolite in carcinogenesis by N-nitrosamines with a 2-hydroxyethyl group.

  从 N-亚硝基-N-（甲酰基甲基）烷基胺（3）中分离出直接作用的诱变剂，并确定其为 N-亚硝基-N-烷基-1-羟基亚氨基-2-氧代乙胺（4）。根据核磁共振波谱阐明了它们的结构，并通过衍生成结晶的 2，4-二硝基苯肼（5）得到了证实。化合物 4（烷基=乙基和丁基）对鼠伤寒沙门氏菌 TA 1535 和大肠杆菌 WP2 hcr- 具有强烈的致突变性，而带有叔丁基的 4 则没有致突变性。4 的形成被认为是通过 3 的亚硝基化进行的，这表明带有 2-羟乙基的 N-亚硝胺可能参与了甲酰基甲基代谢物的致癌过程。
• Suzuki,E.; Okada,M., Chemical and pharmaceutical bulletin, 1979, vol. 27, p. 541 - 544
  作者：Suzuki,E.、Okada,M.

  DOI：——

  日期：——