1,4-Bis(2-cyano-2-methylpropyl)-2,3-(methylenedioxy)benzene | 162659-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1,4-Bis(2-cyano-2-methylpropyl)-2,3-(methylenedioxy)benzene
• 英文别名: 3-[7-(2-Cyano-2-methylpropyl)-1,3-benzodioxol-4-yl]-2,2-dimethylpropanenitrile
• CAS: 162659-11-2
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: SOGJUMDTHRLPKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-Bis(2-cyano-2-methylpropyl)-2,3-(methylenedioxy)benzene 在 盐酸 、 potassium tert-butylate 、 氨 、 叔丁胺 作用下， 反应 1.92h， 生成 6,7-(Methylenedioxy)-3,3,12,12-tetramethyl<4.4>paracyclophane-2,13-dione
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 3,3,12,12-Tetramethyl[4.4]paracyclophane-2,13-dione

  摘要：

  Three [4.4]paracyclophanes (2-4) were synthesized by radical cyclization using the photoinduced S(RN)1 reaction. The structure of the most stable conformer of 4 was ascertained by means of X-ray crystallographic analysis, molecular mechanics calculations, and variable-temperature NMR spectra. The energy barriers to rotation of the two benzene rings in these compounds were obtained from an analysis of the temperature-dependent signals due to the 1,3-dioxolene and aromatic ring protons. Molecular mechanics calculations predicted three stable conformers for 4. Actually, three sets of signals were observed in its low-temperature H-1 NMR spectrum. An experimental technique was used in which crystals were dissolved in precooled solvent. In this manner, NMR signals were recorded due to the single conformer found in its crystalline state, which are identical to the major set of signals present in the original spectrum. The structures due to the other two sets of signals of 4 can;be successfully assigned by comparison of the low temperature H-1 NMR spectra of the two compounds (2 and 3). The interconversion pathways among these conformers were characterized.

  DOI：

  10.1021/jo00111a030
• 作为产物：
  描述：

  1,4-Bis(acetoxymethyl)-2,3-(methylenedioxy)benzene 在 氢溴酸 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 1,4-Bis(2-cyano-2-methylpropyl)-2,3-(methylenedioxy)benzene
  参考文献：
  名称：

  Synthesis and Conformational Analysis of 3,3,12,12-Tetramethyl[4.4]paracyclophane-2,13-dione

  摘要：

  Three [4.4]paracyclophanes (2-4) were synthesized by radical cyclization using the photoinduced S(RN)1 reaction. The structure of the most stable conformer of 4 was ascertained by means of X-ray crystallographic analysis, molecular mechanics calculations, and variable-temperature NMR spectra. The energy barriers to rotation of the two benzene rings in these compounds were obtained from an analysis of the temperature-dependent signals due to the 1,3-dioxolene and aromatic ring protons. Molecular mechanics calculations predicted three stable conformers for 4. Actually, three sets of signals were observed in its low-temperature H-1 NMR spectrum. An experimental technique was used in which crystals were dissolved in precooled solvent. In this manner, NMR signals were recorded due to the single conformer found in its crystalline state, which are identical to the major set of signals present in the original spectrum. The structures due to the other two sets of signals of 4 can;be successfully assigned by comparison of the low temperature H-1 NMR spectra of the two compounds (2 and 3). The interconversion pathways among these conformers were characterized.

  DOI：

  10.1021/jo00111a030