N-亚硝基-N-苄基氨基磺酸钾 | 138337-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-亚硝基-N-苄基氨基磺酸钾
• 中文别名: 硫酰胺酸,亚硝基(苯基甲基)-,盐钾
• 英文名称: potassium N-Nitroso-N-benzylsulfamate
• 英文别名: benzyl-nitroso-amidosulfuric acid ; potassium salt；Benzyl-nitroso-amidoschwefelsaeure; Kaliumsalz；potassium;N-benzyl-N-nitrososulfamate
• CAS: 138337-14-1
• 化学式: C₇H₇N₂O₄S*K
• 分子量: 254.308
• InChiKey: QBCPHMLVLRCNNS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.37
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-亚硝基-N-苄基氨基磺酸钾 以 重水 为溶剂， 反应 0.07h， 生成 potassium benzylidensulfamate
  参考文献：
  名称：

  Alkyldiazonium ion pairs and deamination. 46. N-nitrososulfamates: sources of carbonium ions in aqueous media and substrates in solid-state decompositions

  摘要：

  Potassium N-nitrososulfamates of benzylamine, 2-phenylethylamine, and cyclohexylamine 2a-c were synthesized and examined as sources of carbonium ions in aqueous media. The nitrososulfamates are crystalline compounds which decompose readily at low pHs (approximately 2) under conditions where the parent amines are relatively stable to nitrous acid. In water solutions they produce the corresponding alcohols, principally, along with small percentages of the corresponding esters of potassium bisulfate. The decomposition of the benzyl analogue 2b in the presence of sodium thiocyanate produced, principally, benzyl alcohol, but also benzyl thiocyanate and benzyl isothiocyanate in a ratio of 4.4/1, indicating a muted role for nucleophilicity in this carbonium ion reaction. In sulfate buffers they decompose by psuedo-first-order kinetics (rate constants are reported). In acetic acid they produce principally the corresponding acetate esters. A reaction mechanism is proposed in which the slow step involves the production of diazohydroxide rather than a direct formation of a carbonium ion. The benzyl analogue 2b is an inhibitor of the enzyme pepsin; it also undergoes a photoelimination reaction on irradiation. The nitrososulfamates are perfectly stable when dry, but they undergo a relatively rapid solid-state decomposition (T1/2 almost-equal-to 2-5 days) when exposed to normal atmospheric humidity; surprisingly, the external appearance of the crystals does not change during the decompositions. The products are, principally, the esters of sulfuric acid and potassium bisulfate.

  DOI：

  10.1021/jo00030a037
• 作为产物：
  描述：

  N-苄基氨基磺酸 在 potassium nitrite 作用下， 以 水 为溶剂， 以48%的产率得到N-亚硝基-N-苄基氨基磺酸钾
  参考文献：
  名称：

  Alkyldiazonium ion pairs and deamination. 46. N-nitrososulfamates: sources of carbonium ions in aqueous media and substrates in solid-state decompositions

  摘要：

  Potassium N-nitrososulfamates of benzylamine, 2-phenylethylamine, and cyclohexylamine 2a-c were synthesized and examined as sources of carbonium ions in aqueous media. The nitrososulfamates are crystalline compounds which decompose readily at low pHs (approximately 2) under conditions where the parent amines are relatively stable to nitrous acid. In water solutions they produce the corresponding alcohols, principally, along with small percentages of the corresponding esters of potassium bisulfate. The decomposition of the benzyl analogue 2b in the presence of sodium thiocyanate produced, principally, benzyl alcohol, but also benzyl thiocyanate and benzyl isothiocyanate in a ratio of 4.4/1, indicating a muted role for nucleophilicity in this carbonium ion reaction. In sulfate buffers they decompose by psuedo-first-order kinetics (rate constants are reported). In acetic acid they produce principally the corresponding acetate esters. A reaction mechanism is proposed in which the slow step involves the production of diazohydroxide rather than a direct formation of a carbonium ion. The benzyl analogue 2b is an inhibitor of the enzyme pepsin; it also undergoes a photoelimination reaction on irradiation. The nitrososulfamates are perfectly stable when dry, but they undergo a relatively rapid solid-state decomposition (T1/2 almost-equal-to 2-5 days) when exposed to normal atmospheric humidity; surprisingly, the external appearance of the crystals does not change during the decompositions. The products are, principally, the esters of sulfuric acid and potassium bisulfate.

  DOI：

  10.1021/jo00030a037

文献信息

• Paal; Lowitsch, Chemische Berichte, 1897, vol. 30, p. 879
  作者：Paal、Lowitsch

  DOI：——

  日期：——
• Alkyldiazonium ion pairs and deamination. 46. N-nitrososulfamates: sources of carbonium ions in aqueous media and substrates in solid-state decompositions
  作者：Emil H. White、Min Li、Shanzheng Lu

  DOI：10.1021/jo00030a037

  日期：1992.2

  Potassium N-nitrososulfamates of benzylamine, 2-phenylethylamine, and cyclohexylamine 2a-c were synthesized and examined as sources of carbonium ions in aqueous media. The nitrososulfamates are crystalline compounds which decompose readily at low pHs (approximately 2) under conditions where the parent amines are relatively stable to nitrous acid. In water solutions they produce the corresponding alcohols, principally, along with small percentages of the corresponding esters of potassium bisulfate. The decomposition of the benzyl analogue 2b in the presence of sodium thiocyanate produced, principally, benzyl alcohol, but also benzyl thiocyanate and benzyl isothiocyanate in a ratio of 4.4/1, indicating a muted role for nucleophilicity in this carbonium ion reaction. In sulfate buffers they decompose by psuedo-first-order kinetics (rate constants are reported). In acetic acid they produce principally the corresponding acetate esters. A reaction mechanism is proposed in which the slow step involves the production of diazohydroxide rather than a direct formation of a carbonium ion. The benzyl analogue 2b is an inhibitor of the enzyme pepsin; it also undergoes a photoelimination reaction on irradiation. The nitrososulfamates are perfectly stable when dry, but they undergo a relatively rapid solid-state decomposition (T1/2 almost-equal-to 2-5 days) when exposed to normal atmospheric humidity; surprisingly, the external appearance of the crystals does not change during the decompositions. The products are, principally, the esters of sulfuric acid and potassium bisulfate.