1-(1-Methyl-2-hydroxyethoxy)-2-oxo-3,3-diethyl-1-triazene | 143706-19-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-(1-Methyl-2-hydroxyethoxy)-2-oxo-3,3-diethyl-1-triazene
• 英文别名: (Z)-diethylamino-(1-hydroxypropan-2-yloxyimino)-oxidoazanium
• CAS: 143706-19-8
• 化学式: C₇H₁₇N₃O₃
• 分子量: 191.23
• InChiKey: AERYIRXPRBJJIY-NTMALXAHSA-N

物化性质

• 沸点：
  276.8±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.13
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  sodium N,N-(diethylamino)diazen-1-ium-1,2-diolate 、 methyloxirane 以 四氢呋喃 为溶剂， 反应 20.0h， 以6%的产率得到1-(2-Hydroxypropoxy)-2-oxo-3,3-diethyl-1-triazene
  参考文献：
  名称：

  Secondary amine/nitric oxide complex ions, R2N[N(O)NO]-. O-Functionalization chemistry

  摘要：

  Alkylation of the R2N[N(O)NO]- anion has been studied with the aim of extending the reaction's scope, probing its stereochemistry, and exploring the reactivity of its variously functionalized products. Using the sodium salt of the R = Et ion (1) as the standard starting material, numerous novel products having the structure Et2N[N2O2]R]' (2) were isolated from its reaction with alkyl halides, sulfate esters, and oxiranes. In addition to previously described examples in which R' is a simple straight-chain alkyl or benzyl group, new compound types in which R' is hydroxylated, halide-containing, alpha-methoxylated, and olefinic were prepared. The 2-bromoethyl derivative could be dehydrohalogenated to the O-vinyl compound or further reacted with other nucleophiles such as amines, water, or a second mole of 1 to produce additional new compound types. Ethylation of 1 appeared to occur exclusively at the terminal oxygen to give Et2NN(O)=NOEt as the only isomer detected; this conclusion regarding the regiochemistry of the reaction conflicts with that found in the previous literature, but its generality was supported by X-ray crystallographic analysis of the Et2NN(O)=NOCH2CH2(NC5H5)+Br- analogue. Hydrolytic decomposition of 2 was slow, even for the O-vinyl and -methoxymethyl derivatives, as reflected in the sluggish loss of the intense chromophore these compounds characteristically show at 225-245 nm (epsilon (6.5-9) x 10(3) M-1 cm-1); half-lives at 37-degrees-C for the latter two compounds were 12 h in 0.1 M HCl and 9 h in 1 M HCl respectively. N-Nitrosodiethylamine was a frequent byproduct of both the synthesis and hydrolysis of 2. The results should aid the effort to design prodrug derivatives of 1, a compound type which has recently been shown to exhibit useful pharmacological effects.

  DOI：

  10.1021/jo00049a017

文献信息

• Secondary amine/nitric oxide complex ions, R2N[N(O)NO]-. O-Functionalization chemistry
  作者：Joseph E. Saavedra、Tambra M. Dunams、Judith L. Flippen-Anderson、Larry K. Keefer

  DOI：10.1021/jo00049a017

  日期：1992.11

  Alkylation of the R2N[N(O)NO]- anion has been studied with the aim of extending the reaction's scope, probing its stereochemistry, and exploring the reactivity of its variously functionalized products. Using the sodium salt of the R = Et ion (1) as the standard starting material, numerous novel products having the structure Et2N[N2O2]R]' (2) were isolated from its reaction with alkyl halides, sulfate esters, and oxiranes. In addition to previously described examples in which R' is a simple straight-chain alkyl or benzyl group, new compound types in which R' is hydroxylated, halide-containing, alpha-methoxylated, and olefinic were prepared. The 2-bromoethyl derivative could be dehydrohalogenated to the O-vinyl compound or further reacted with other nucleophiles such as amines, water, or a second mole of 1 to produce additional new compound types. Ethylation of 1 appeared to occur exclusively at the terminal oxygen to give Et2NN(O)=NOEt as the only isomer detected; this conclusion regarding the regiochemistry of the reaction conflicts with that found in the previous literature, but its generality was supported by X-ray crystallographic analysis of the Et2NN(O)=NOCH2CH2(NC5H5)+Br- analogue. Hydrolytic decomposition of 2 was slow, even for the O-vinyl and -methoxymethyl derivatives, as reflected in the sluggish loss of the intense chromophore these compounds characteristically show at 225-245 nm (epsilon (6.5-9) x 10(3) M-1 cm-1); half-lives at 37-degrees-C for the latter two compounds were 12 h in 0.1 M HCl and 9 h in 1 M HCl respectively. N-Nitrosodiethylamine was a frequent byproduct of both the synthesis and hydrolysis of 2. The results should aid the effort to design prodrug derivatives of 1, a compound type which has recently been shown to exhibit useful pharmacological effects.