2,2-dimethyl-5,5-dinitro-1,3-dioxane | 5086-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5,5-dinitro-1,3-dioxane
• 英文别名: 2,2-dimethyl-5,5-dinitro-[1,3]dioxane；2,2-Dimethyl-5,5-dinitro-[1,3]dioxan
• CAS: 5086-75-9
• 化学式: C₆H₁₀N₂O₆
• 分子量: 206.155
• InChiKey: CLCUHNNEIHFIEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5,5-dinitro-1,3-dioxane 在 sodium sulfide 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.5h， 生成 2,2,2'-2'-tetramethyl 1,3,1',3'-bis Δ5,5'-dioxane
  参考文献：
  名称：

  Préparation et évaluation antiparasitaire de nouveaux imidazoles portant le motif dioxane ou hexahydropyrimidine

  摘要：

  5-Nitro-1,3-dioxane and 5-nitrohexahydropyrimidine salts are found to be suitable nucleophiles for S(RN)1 reactions. From C-alkylation products, base-promoted nitrous acid elimination and acid-catalyzed cleavage of the resulting acetals afford new compounds. Only the imidazole derivatives exhibit significant amoebicide and trichomonacide activities. Structure-activity relationships are discussed.

  DOI：

  10.1016/0223-5234(91)90120-c
• 作为产物：
  描述：

  4-甲砜基苯甲酸 在 sodium dithionate 、 potassium hexacyanoferrate(III) 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 2,2-dimethyl-5,5-dinitro-1,3-dioxane
  参考文献：
  名称：

  Préparation et évaluation antiparasitaire de nouveaux imidazoles portant le motif dioxane ou hexahydropyrimidine

  摘要：

  5-Nitro-1,3-dioxane and 5-nitrohexahydropyrimidine salts are found to be suitable nucleophiles for S(RN)1 reactions. From C-alkylation products, base-promoted nitrous acid elimination and acid-catalyzed cleavage of the resulting acetals afford new compounds. Only the imidazole derivatives exhibit significant amoebicide and trichomonacide activities. Structure-activity relationships are discussed.

  DOI：

  10.1016/0223-5234(91)90120-c

文献信息

• Electron transfer reactivity in 5-nitrouracil series
  作者：Michel P. Crozet、Armand Gellis、Christian Pasquier、Patrice Vanelle、Jean-Pierre Aune

  DOI：10.1016/0040-4039(94)02304-t

  日期：1995.1

  shown to react with various reductive alkylating agents such as p-nitrobenzyl chloride and dinitropropane by an SRN1 mechanism to give new potentially bioactive 5-nitrouracil derivatives. 1,3-Dimethyl-5-nitro-6-chloromethyluracil also reacts by an SRN1 mechanism with 2-nitropropane anion to afford a new uracil derivative bearing a trisubstituted ethylenic double bond at the 6-position.

  1，3，6-三甲基-5-硝基尿嘧啶的钠盐显示通过S RN 1机理与各种还原性烷基化剂（例如对硝基苄基氯和二硝基丙烷）反应生成新的具有潜在生物活性的5-硝基尿嘧啶衍生物。1，3-二甲基-5-硝基-6-氯甲基尿嘧啶也通过S RN 1机理与2-硝基丙烷阴离子反应，得到新的尿嘧啶衍生物，其在6-位带有三取代的烯键式双键。
• Synthesis of heterocyclic geminal nitro azides
  作者：D. V. Katorov、G. F. Rudakov、V. F. Zhilin

  DOI：10.1007/s11172-009-0323-9

  日期：2009.11

  The oxidative azidation reactions of C-nitro-substituted saturated heterocyclic compounds, viz., the nitro derivatives of oxetane, azetidine, 1,3-dioxane, tetrahydro-1,3-oxazine, and hexahydropyrimidine, were investigated. A novel representatives of the geminal nitro azides were prepared and their physicochemical properties were studied. The process of the formation of the geminal dinitro compounds

  研究了C-硝基取代的饱和杂环化合物的氧化叠氮化反应，即氧杂环丁烷、氮杂环丁烷、1,3-二恶烷、四氢-1,3-恶嗪和六氢嘧啶的硝基衍生物。制备了一种新型的孪生硝基叠氮化物的代表物并研究了它们的理化性质。分析了氧化叠氮化形成孪生二硝基化合物的过程。
• 3,4-Bis(α-nitroalkyl-ONN-azoxy)furazans and some of their derivatives
  作者：O. A. Luk’yanov、G. V. Pokhvisneva、T. V. Ternikova、N. I. Shlykova

  DOI：10.1007/s11172-012-0050-5

  日期：2012.2

  Reaction of pseudonitroles and their derivatives with diaminofurazan in the presence of dibromoisocyanuric acid (DBI) resulted in symmetrical 3,4-bis(-nitroalkyl-ONN-azoxy)-furazans or their derivatives. For the synthesis of bis(nitroalkyl-ONN-azoxy)furazans bearing various a-nitroalkyl-ONN-azoxy groups, the method based on the reaction of α-nitronitroso compounds with 3-amino-4-(nitroalkyl)-ONN-azoxy)furazans (in the presence of DBI) was developed. Synthetic procedures towards aforementioned compounds with nitromethyl-, dibromonitromethyl-, trinitromethyl-ONN-azoxy and other groups were described.

  伪硝酮及其衍生物在二溴异氰尿酸（DBI）的存在下与二氨基呋咱反应，生成了对称的3,4-双（-硝基烷基-ONN-偶氮基）呋咱或其衍生物。为了合成具有不同α-硝基烷基-ONN-偶氮基的双（硝基烷基-ONN-偶氮基）呋咱，开发了一种基于α-硝基亚硝基化合物与3-氨基-4-（硝基烷基）-ONN-偶氮基呋咱反应的方法（在DBI的存在下）。描述了合成上述含有硝基甲基、二溴硝基甲基、三硝基甲基-ONN-偶氮基及其他基团的化合物的合成程序。
• Nitro-substituted bis(methyl-ONN-azoxyfurazanyl)furoxans
  作者：O. A. Luk’yanov、G. V. Pokhvisneva、T. V. Ternikova

  DOI：10.1007/s11172-015-0832-7

  日期：2015.1

  Reaction of bis(aminofurazanyl)furoxan with 2,2-dimethyl-5-nitro-5-nitroso-1,3-dioxane in the presence of dibromoisocyanurate and a series of subsequent transformations give rise to the following bis(mononitroalkyland polynitromethyl-ONN-azoxyfurazanyl)furoxans: bis(nitromethyl-ONN-azoxyfurazanyl)furoxan, bis(dinitromethyl-ONN-azoxyfurazanyl)furoxan, bis(trinitromethyl-ONN-azoxyfurazanyl)furoxan, and a

  双（氨基呋喃基）呋喃与 2,2-二甲基-5-硝基-5-亚硝基-1,3-二恶烷在二溴异氰脲酸酯和一系列后续转化的存在下反应产生以下双（单硝基烷基和多硝基甲基-ONN- azoxyfurazanyl)furoxan：双(硝基甲基-ONN-azoxyfurazanyl)furoxan、双(dinitromethyl-ONN-azoxyfurazanyl)furoxan、bis(trinitromethyl-ONN-azoxyfurazanyl)furoxan，以及它们的许多衍生物，包括双(fluorodinitrometyl-ONN-azoxy)呋喃西林
• Reactions SRN1 en serie heterocyclique: IV: Reactivite des sels du dimethyl-2,2 nitro-5 dioxanne-1,3
  作者：Michel P Crozet、Gaëlle Archaimbault、Patrice Vanelle、Robert Nouguier

  DOI：10.1016/s0040-4039(00)98882-8

  日期：1985.1

  2-Alkyl 2-nitro 1,3-propanediol, 2-alkylidene 1,3-propanediol and 2-dialkylidene 1,3-propanediol are prepared via SRN1 reactions with salts of 2,2-dimethyl 5-nitro 1,3-dioxane and acid-catalyzed cleavage of the resulting acetals.

  通过S RN 1反应与2,2-二甲基5-硝基1,3的盐制备2-烷基2-硝基1,3-丙二醇，2-亚烷基1,3-丙二醇和2-二亚烷基1,3-丙二醇-二恶烷和酸催化裂解所产生的缩醛。