4-methyl-2-(3-nitro-phenyl)-[1,3]dioxolane | 72024-78-3

• 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: 4-methyl-2-(3-nitro-phenyl)-[1,3]dioxolane
• 英文别名: 4-Methyl-2-(3-nitro-phenyl)-[1,3]dioxolan；4-Methyl-2-(3-nitrophenyl)-1,3-dioxolane
• CAS: 72024-78-3
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: NCABOERLZUBBNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2-丙二醇 、 间硝基苯甲醛 在 amberlite IR 120 (nuclear sulfonic acid type) 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 4-methyl-2-(3-nitro-phenyl)-[1,3]dioxolane
  参考文献：
  名称：

  A New Approach to the Synthesis of 2-Nitrobenzaldehyde. Reactivity and Molecular Structure Studies

  摘要：

  New approaches to the synthesis of 2-nitrobenzaldehyde by formation and selective isomer separation of 2-nitrophenyl-1,3-dioxolane and further hydrolysis are reported. In this route, the same acidic heterogeneous catalyst is used for 1,3-dioxolane formation and hydrolysis; it can be recycled several times without loss of efficiency. The ortholmeta isomers of 2-nitrophenyl-1,3-dioxolane can be separated by a combination of stereoselective crystallization and fractionated distillation. This new route reduces safety and environmental hazards in the synthesis of 2-nitro- and 3-nitro-benzaldehydes. The molecular structures of the nitro derivatives were confirmed by H-1 and C-13 NMR spectroscopy. The results are in accordance with a non-coplanar conformer of the,2-nitro derivatives (2-nitrobenzaldehyde and 2-(2'-nitrophenyl)-1,3-dioxolane), where the nitro group is twisted with respect to the phenyl ring. In contrary, both the carbonyl and the nitro group are coplanar with the phenyl ring in 3-nitrobenzaldehyde. This result is consistent with the reactivity of the compounds.

  DOI：

  10.1007/s007060270002

文献信息

• Ovchinnikov, V. V.; Evstaf'eva, Yu. G.; Latypova, V. Z., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 1, p. 196 - 199
  作者：Ovchinnikov, V. V.、Evstaf'eva, Yu. G.、Latypova, V. Z.、Bogoveeva, G. A.、Cherkasov, R. A.

  DOI：——

  日期：——
• Salmi; Kyrki, Suomen Kemistilehti B, 1946, vol. 19, p. 97,100
  作者：Salmi、Kyrki

  DOI：——

  日期：——
• Fieser et al., Journal of Biological Chemistry, 1944, vol. 156, p. 191,195
  作者：Fieser et al.

  DOI：——

  日期：——
• KANTLEHNER W.; GUTBROD H.-D., LIEBIGS ANN. CHEM., 1979, NO 9, 1362-1369
  作者：KANTLEHNER W.、 GUTBROD H.-D.

  DOI：——

  日期：——
• A New Approach to the Synthesis of 2-Nitrobenzaldehyde. Reactivity and Molecular Structure Studies
  作者：C. Ignacio Sainz-Díaz

  DOI：10.1007/s007060270002

  日期：2002.1

  New approaches to the synthesis of 2-nitrobenzaldehyde by formation and selective isomer separation of 2-nitrophenyl-1,3-dioxolane and further hydrolysis are reported. In this route, the same acidic heterogeneous catalyst is used for 1,3-dioxolane formation and hydrolysis; it can be recycled several times without loss of efficiency. The ortholmeta isomers of 2-nitrophenyl-1,3-dioxolane can be separated by a combination of stereoselective crystallization and fractionated distillation. This new route reduces safety and environmental hazards in the synthesis of 2-nitro- and 3-nitro-benzaldehydes. The molecular structures of the nitro derivatives were confirmed by H-1 and C-13 NMR spectroscopy. The results are in accordance with a non-coplanar conformer of the,2-nitro derivatives (2-nitrobenzaldehyde and 2-(2'-nitrophenyl)-1,3-dioxolane), where the nitro group is twisted with respect to the phenyl ring. In contrary, both the carbonyl and the nitro group are coplanar with the phenyl ring in 3-nitrobenzaldehyde. This result is consistent with the reactivity of the compounds.