3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide | 13456-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide
• 英文别名: 3,5-dichloro-2,4,6-trimethylbenzonitrile oxide；Benzonitrile, 3,5-dichloro-2,4,6-trimethyl-, N-oxide
• CAS: 13456-86-5
• 化学式: C₁₀H₉Cl₂NO
• 分子量: 230.094
• InChiKey: UFELWQICZDNRND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide 在 4-氨基吡啶 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以54%的产率得到3,5-bis(3,5-dichloro-2,4,6-trimethylphenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  稳定的苯甲腈氧化物与氨基吡啶的反应

  摘要：

  DOI：

  10.3987/com-00-8946
• 作为产物：
  描述：

  3,5-dichloro-N-hydroxy-2,4,6-trimethyl-benzimidoyl chloride 在 盐酸 、 potassium chloride 作用下， 以 甲醇 为溶剂， 生成 3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide
  参考文献：
  名称：

  Beltrame, Paolo; Carniti, Paolo; Gelli, Gioanna, Gazzetta Chimica Italiana, 1980, vol. 110, # 11/12, p. 603 - 608

  摘要：

  DOI：

文献信息

• Stable nitrile oxide dipolar cycloadditions in pure water
  作者：Giorgio Molteni、Paola Del Buttero

  DOI：10.1016/j.tet.2011.07.037

  日期：2011.9

  A systematic study on the behaviour of stable 2,4,6-trimethyl-3,5-dichlorobenzonitrile oxide versus a number of mono-, bi- and trisubstituted dipolarophiles in water was pursued obtaining simple as well as annulated isoxazolines. Reaction conditions changed with the dipolarophilic species, according to their solubility in water and the degree of substitution of the reactive carbon–carbon multiple bond

  进行了系统的研究，研究了稳定的2,4,6-三甲基-3,5-二氯苄腈氧化物与许多单，双和三取代的双亲性亲油性在水中的行为，从而获得了简单的和环化的异恶唑啉。根据其在水中的溶解度和反应性碳-碳多键的取代程度，反应条件随亲双性物质而变化。还测试了十二烷基硫酸钠的存在作为潜在的胶束催化剂。
• Isothiazoles. Part VIII. Thermal rearrangement to α,β-unsaturated nitriles of cycloadducts from 3-diethylamino-4-(4-methoxyphenyl)-5-vinyl-isothiazole 1,1-dioxide with nitrile oxides and münchnones
  作者：Francesca Clerici、Maria Luisa Gelmi、Raffaella Soave、Marinella Valle

  DOI：10.1016/s0040-4020(98)00668-1

  日期：1998.9

  3-Diethylamino-4-(4-methoxyphenyl)-5-vinyl-isothiazole 1,1-dioxide was reacted with nitrile oxides and münchnones affording the cycloadducts in good yields. The cycloaddition reaction occurred at the vinyl group exclusively. The cycloadducts undergo pyrolytic transformation into α,β-unsaturated nitriles through the isoxazole-or pyrrole-isothiazoline 1,1-dioxide intermediates.

  使3-二乙氨基-4-（4-甲氧基苯基）-5-乙烯基-异噻唑1,1-二氧化物与氧化腈和慕尼黑酯反应，以高收率得到环加合物。环加成反应仅在乙烯基上发生。环加合物通过异恶唑-或吡咯-异噻唑啉1,1-二氧化物中间体热解转变为α，β-不饱和腈。
• Cycloaddition of 1,3-dipoles to bullvalene
  作者：A.Gamba Invernizzi、R. Gandolfi、M. Strigazzi

  DOI：10.1016/s0040-4020(01)90657-x

  日期：1974.1

  and other 1,3-dipoles (diphenylnitrilimine, 3,4-dihydroisoquinoline-N-oxide and diazoethane) has been studied. The 3 + 2 → 5 cycloaddition is perispecific. Valence tautomerism of the cycloadducts is evaluated and the influence of the substituents in the isoxazoline ring is briefly discussed.

  已经研究了牛戊烯对几种腈氧化物和其他1,3-偶极子（二苯基硝胺，3,4-二氢异喹啉-N-氧化物和重氮乙烷）的偶极亲和性。3 + 2→5环加成是特异性的。评价环加合物的价互变异构，并简要讨论异恶唑啉环中取代基的影响。
• 1,3-Dipolar cycloaddition reactions of polycyclic aromatic hydrocarbons with 3,5-dichloro-2,4,6-trimethyl- and 2,4,6-trimethylbenzonitrile oxide
  作者：Antonino Corsaro、Vito Librando、Ugo Chiacchio、Venerando Pistarà

  DOI：10.1016/0040-4020(96)00783-1

  日期：1996.9

  and perylene, but not to naphthalene and triphenylene, to give a regioisomeric monocycloadduct. Anthracene give also the two corresponding biscycloadducts. The site- and regio-selectivity of the reactions of the anthracene and pyrene is discussed in terms of FMO approximation.

  标题1，3-偶极加到菲，pyr，蒽和per上，但不加到萘和三亚苯上，得到区域异构的单环加合物。蒽还给出两个相应的双环加合物。蒽和pyr的反应的位点和区域选择性是根据FMO近似进行讨论的。
• N,N-Disubstituted propargylamines as tools in the sequential 1,3-dipolar cycloaddition/arylation processes to the formation of polyheterocyclic systems
  作者：Luca Basolo、Egle M. Beccalli、Elena Borsini、Gianluigi Broggini、Sara Pellegrino

  DOI：10.1016/j.tet.2008.06.042

  日期：2008.8

  Starting from N,N-disubstituted propargylamines, through a one-pot sequential 1,3-dipolar cycloaddition/Pd-catalyzed arylation, polyheterocyclic systems were obtained in only one step. The outcome of the cycloadditions, performed with 1,3-dipoles nitriloxide and azide, was totally regioselective. The subsequent Pd-catalyzed arylation achieved using ligand-free conditions involved the unsubstituted

  从N，N-二取代的炔丙基胺开始，通过一锅顺序的1，3-偶极环加成/ Pd催化的芳基化，仅一步就获得了多杂环体系。用1，3-偶极氮氧化物和叠氮化物进行的环加成反应的结果是完全区域选择性的。使用不含配体的条件实现的后续Pd催化的芳基化反应涉及杂环的未取代碳。