1-(2-Hydroxyethoxy)-2-oxo-3,3-diethyl-1-triazene | 143706-23-4

• 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-(2-Hydroxyethoxy)-2-oxo-3,3-diethyl-1-triazene
• 英文别名: (Z)-diethylamino-(2-hydroxyethoxyimino)-oxidoazanium
• CAS: 143706-23-4
• 化学式: C₆H₁₅N₃O₃
• 分子量: 177.203
• InChiKey: KEDAXAIFVKUMAA-CLFYSBASSA-N

物化性质

• 沸点：
  266.8±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  sodium N,N-(diethylamino)diazen-1-ium-1,2-diolate 、 2-溴乙醇 以 四氢呋喃 为溶剂， 以33%的产率得到1-(2-Hydroxyethoxy)-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

• OXYGEN SUBSTITUTED DERIVATIVES OF NUCLEOPHILE-NITRIC OXIDE ADDUCTS AS NITRIC OXIDE DONOR PRODRUGS
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by the SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP0605622B1

  公开（公告）日：1997-11-12
• US5366997A
  申请人：——

  公开号：US5366997A

  公开（公告）日：1994-11-22
• [EN] OXYGEN SUBSTITUTED DERIVATIVES OF NUCLEOPHILE-NITRIC OXIDE ADDUCTS AS NITRIC OXIDE DONOR PRODRUGS
  申请人：THE UNITED STATES OF AMERICA, represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：WO1993007114A1

  公开（公告）日：1993-04-15

  (EN) There are disclosed cardiovascularly active compounds possessing antihypertensive properties, and pharmaceutical compositions containing these agents and a method of treating cardiovascular disorders with the compounds. The active components of the pharmaceutical compositions are compounds of formula (I) wherein R1 and R2 are independently chosen from straight chain and branched chain alkyl and olefinic groups, which may be unsubstituted or substituted; or R1 and R2 together with the nitrogen atom they are bonded to form a heterocyclic group; and R3 is a pharmaceutically acceptable organic group selected from alkyl and olefinic groups which may be unsubstituted or substituted, acyl, a sulfonyl, sulfinyl, sulfenyl, carbonate, or carbamate derivative; or R3 is a group of the formula: (CH2)nONN(O)NR1R2, wherein n is 2-8, and R1 and R2 are as described above. Novel compounds are disclosed wherein at least one of R1, R2 and R3 is an olefinic group or heteroatom-substituted straight or branched chain alkyl or olefinic group. Novel methods of synthesizing the compounds are also disclosed.(FR) L'invention concerne des composés présentant une activité cardiovasculaire et possédant des propriétés anti-hypertensives, ainsi que des compositions pharmaceutiques contenant ces agents et un procédé de traitement de troubles cardiovasculaires au moyen de ces derniers. Les composants actifs des compositions pharmaceutiques sont des composés de la formule (I), dans laquelle R1 et R2 sont choisis indépendamment parmi des groupes alkyle et oléfinique à chaîne droite et à chaîne ramifiée, lesquels peuvent être non substitués ou substitués; ou R1 et R2 avec l'atome d'azote auquel ils sont fixés forment un groupe hétérocyclique; et R3 représente un groupe organique pharmaceutiquement acceptable choisi parmi des groupes alkyle et oléfinique pouvant être non substitués ou substitués, acyle, un dérivé sulfonyle, sulfinyle, sulfényle, carbonate ou carbamate; ou R3 représente un groupe de la formule: (CH2)nONN(O)NR1R2, dans laquelle n est compris entre 2 et 8, et R1 ainsi que R2 ont la notation ci-définie. L'invention concerne également des nouveaux composés dans lesquels R1 et/ou R2 et/ou R3 représentent un groupe oléfinique ou un groupe alkyle ou oléfinique à chaîne droite ou ramifiée à substitution d'hétéroatomes. En outre, l'invention concerne de nouveaux procédés de synthèse des composés.
• 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.