1-((Methoxymethyl)oxy)-2-oxo-3,3-diethyl-1-triazene | 143706-25-6

• 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-((Methoxymethyl)oxy)-2-oxo-3,3-diethyl-1-triazene
• 英文别名: 1-[(Methoxymethyl)oxy]-2-oxo-3,3-diethyl-1-triazene；DEA/NO: methoxymethyl ether；(Z)-diethylamino-(methoxymethoxyimino)-oxidoazanium
• CAS: 143706-25-6
• 化学式: C₆H₁₅N₃O₃
• 分子量: 177.203
• InChiKey: MOBRKEKGWCQYHC-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  62.8
• 氢给体数：
  0
• 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 、 氯甲基甲基醚 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以41%的产率得到1-((Methoxymethyl)oxy)-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

• ENDOTHELIUM MIMICKING NANOMATRIX
  申请人：Jun Ho-Wook

  公开号：US20100119573A1

  公开（公告）日：2010-05-13

  Disclosed herein are peptide amphiphiles for use in producing a natural endothelium mimicking nanomatrix. The disclosed natural endothelium mimicking nanomatrix can be used to coat medical devices such as vascular stents to promote endothelializaiton and inhibit restenosis and thrombosis. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
• CYCLOHEXYL UREA MODULATORS OF D2 RECEPTORS AND/OR D3 RECEPTORS
  申请人：Auspex Pharmaceuticals, Inc.

  公开号：US20140178503A1

  公开（公告）日：2014-06-26

  The present invention relates to new cyclohexyl urea modulators of D2 receptors and/or modulators of D3 receptors, pharmaceutical compositions thereof, and methods of use thereof.
• US8735354B2
  申请人：——

  公开号：US8735354B2

  公开（公告）日：2014-05-27
• 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.