N-亚硝基-N-(乙酰氧基甲基)丁胺 | 56986-36-8

• 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-(乙酰氧基甲基)丁胺
• 英文名称: (N-nitroso-butylamino) methyl acetate
• 英文别名: N-nitroso-N-(acetoxymethyl)butylamine；(N-Nitrosobutylamino)methyl acetate；N-Acetoxymethyl-N-nitrosobutylamin；N-n-Butyl-N-(acetoxymethyl)nitrosamin；N-Butyl-N-(acetoxymethyl)nitrosamine；[butyl(nitroso)amino]methyl acetate
• CAS: 56986-36-8
• 化学式: C₇H₁₄N₂O₃
• 分子量: 174.2
• InChiKey: YMUAXKYTHNCMAS-UHFFFAOYSA-N

物化性质

• 沸点：
  305.17°C (rough estimate)
• 密度：
  1.2227 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  5

制备方法与用途

类别：有毒物质

毒性分级：中毒

急性毒性：

• 口服-大鼠 LD50: 1500 毫克/公斤

可燃性危险特性：热分解排出有毒氮氧化物烟雾

储运特性：库房通风、低温干燥

灭火剂：水、干粉、二氧化碳、泡沫

反应信息

• 作为反应物：
  描述：

  N-亚硝基-N-(乙酰氧基甲基)丁胺 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以29%的产率得到N-butyl-N-(hydroperoxymethyl)nitrosamine
  参考文献：
  名称：

  由正烷基-正-（1-乙酰氧基烷基）亚硝胺形成正烷基-正（1-氢过氧烷基）亚硝胺

  摘要：

  N-烷基-N-（1-氢过氧烷基）亚硝胺是通过酸催化的亲核取代反应，在乙酸中用过氧化氢处理相应的1-乙酰氧基烷基亚硝胺来制备的。

  DOI：

  10.1016/s0040-4039(00)77830-0
• 作为产物：
  描述：

  N-methylidenebutylamine 在 亚硝酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 N-亚硝基-N-(乙酰氧基甲基)丁胺
  参考文献：
  名称：

  Mueller, Eduard; Kettler, Regina; Wiessler, Manfred, Liebigs Annalen der Chemie, 1984, # 8, p. 1468 - 1493

  摘要：

  DOI：

文献信息

• Secondary α-deuterium kinetic isotope effects in the decomposition of simple α-acetoxydialkylnitrosamines: Nitrosiminium ion intermediates
  作者：Hongliang Cai、James C. Fishbein

  DOI：10.1016/s0040-4020(97)00687-x

  日期：1997.8

  Secondary α-deuterium kinetic isotope effects for the pH independent decay of two (N-nitrosoalkylamino)methylacetates (4) and two (N-nitrosoalkylamino)propyl acetates (5) have been determined at 52 °C in aqueous solution, ionic strength 1 M. In all cases the isotope effects are kobsdH/kobsdD ∼ 1.1 – 1.2 (per hydrogen). It is concluded that the direction and magnitude of the isotope effects are inconsistent

  已确定在52°C的水溶液中，离子强度为1 M时，两种（N-亚硝基烷基氨基）甲基乙酸酯（4）和两种（N-亚硝基烷基氨基）丙基乙酸酯（5）的pH值随衰减而变的次级α-氘动力学同位素效应。在所有情况下的同位素效应k个实测值ħ / K实测值d〜1.1 - 1.2（每氢）。结论是同位素作用的方向和幅度与羰基限速反应的机理不一致。并且与在限速步骤中或之前的N-亚硝基亚胺离子的形成是一致的。
• Syntheses of N-alkyl-N-(.ALPHA.-acetoxyalkyl)nitrosamines, model compounds for metabolically activated N,N-dialkylnitrosamines.
  作者：MASATAKA MOCHIZUKI、TAKAKO ANJO、MASASHI OKADA

  DOI：10.1248/cpb.26.3905

  日期：——

  Syntheses of a series of new N, N-dialkylnitrosamines monosubstituted at the α-carbon with an acetoxy group were reported. They were prepared by the procedures reported earlier, but a new procedure was provided, according to which N-alkyl-N-(methoxymethyl)-nitrosamines were converted into N-alkyl-N-(acetoxymethyl) nitrosamines in low but satisfactory yield by refluxing them in acetic acid. The (E)-(Z) conformer ratios of these compounds determined by nuclear magnetic resonance measurement were given.

  报告了一系列在 α 碳上用乙酰氧基单取代的新型 N，N-二烷基亚硝胺的合成。根据该程序，N-烷基-N-（甲氧基甲基）亚硝胺通过在乙酸中回流转化为 N-烷基-N-（乙酰氧甲基）亚硝胺，产量低但令人满意。通过核磁共振测量确定了这些化合物的(E)-(Z)构象比。
• Reexamination of the Mechanisms of Decomposition of Simple .alpha.-Acetoxynitrosamines in the Physiological pH Range
  作者：Cynthia Revis、Markku Rajamaki、James C. Fishbein

  DOI：10.1021/jo00129a011

  日期：1995.12

  Rate constants, k(0), for the buffer independent decay of eight alpha-(acyloxy)nitrosamines were determined in aqueous media, 25 degrees C, ionic strength 1 M (NaClO4), 1% (v/v) in acetonitrile in the pH range 2-13. The pH-rate profile of log k(0) against pH, from pH 2 to 13, indicates a rate law that includes two terms: k(1), a pH independent term, and k(OH), a hydroxide ion dependent term. Values of the entropy of activation for the pH independent reactions of 1-(N-nitrosoethylamino)ethyl acetate (3), (N-nitrosomethylamino)methyl acetate (1), and (N-nitrosobutylamino)methyl acetate (9) are determined to be Delta S-double dagger = 0.7 (+/-1.5), 3 (+/-3), and -5 (+/-3) cal deg(-1) mol(-1), respectively. (N-Nitrosobutylamino)methyl benzoate (11) and (N-nitrosobutylamino)methyl pivaloate (12) decompose with pH independent rate constants that are larger than that of the corresponding acetate 9 by factors of 2.3 and 3.4, respectively. The value of rho(*) for allkyl substituents attached to nitrogen; not containing the acetoxy group, is rho(*) = -5.99 for four methyl acetates. It is concluded that the pH independent decomposition involves the formation of N-nitrosiminium ion intermediates. The greater reactivity of the benzoate and pivaloate, compared to the acetate, in the case of (N-nitrosobutylamino)methyl esters, combined with the product analysis previously reported for the reaction of the ethyl acetates indicates no measurable anchimeric assistance in the decay of the Z forms of the alpha-(acyloxy)nitrosamines studied in the present report. The value of rho(*) for the pH independent decay of the ethyl acetates is rho(*) = -1.50. The smaller value, in comparison to that for the methyl acetates, is ascribed either to a change in transition structure or to a difference, between methyl and ethyl acetates, in the nature of the rate-limiting step of the reactions. The rate constants, k(OH), for the hydroxide ion-catalyzed decay of (N-nitrosobutylamino)methyl benzoate (11) and (N-nitrosobutylamino)methyl pivaloate (12) are smaller than that for the corresponding acetate 9 by factors of 7 and 16, respectively. This observation is consistent with the deduction of others that the mechanism of this reaction involves a rate-limiting reaction at the carbonyl group.
• Isolation and characterization of N-alkyl-N- (hydroxymethyl)nitrosamines from N-alkyl-N- (hydroperoxymethyl)nitrosamines by deoxygenation
  作者：Masataka Mochizuki、Takako Anjo、Masashi Okada

  DOI：10.1016/s0040-4039(00)78747-8

  日期：——
• MOCHIZUKI MASATAKA; ANJO TAKAKO; WAKABAYASHI YUKO; SONE TOSHIE; OKADA MAS+, TETRAHEDRON LETT., 1980, 21, NO 18, 1761-1764
  作者：MOCHIZUKI MASATAKA、 ANJO TAKAKO、 WAKABAYASHI YUKO、 SONE TOSHIE、 OKADA MAS+

  DOI：——

  日期：——