dimethyl 1,4-dihydro-1,4,5,8-tetramethyl-1,4-ethenonaphthalene-2,3-dicarboxylate | 147240-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl 1,4-dihydro-1,4,5,8-tetramethyl-1,4-ethenonaphthalene-2,3-dicarboxylate
• 英文别名: dimethyl 1,3,6,8-tetramethyltricyclo[6.2.2.02,7]dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylate
• CAS: 147240-77-5
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: WXDJYOIHAKNIFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  dimethyl 1,4-dihydro-1,4,5,8-tetramethyl-1,4-ethenonaphthalene-2,3-dicarboxylate 以 苯 为溶剂， 生成 1,2a,3,6-Tetramethyl-2a,6c-dihydro-benzo[a]cyclopropa[cd]pentalene-2b,6b-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Novel photochemistry of a sterically crowded monobenzobarrelene derivative

  摘要：

  The solution phase photochemistry of the sterically congested tetramethylated benzobarrelene derivative 2b differs completely from that of its non-methylated counterpart, 2a. Based on molecular mechanics calculations, the factor that is suggested to be responsible for this difference is relief of the unfavorable methyl-methyl interactions present in 2b.

  DOI：

  10.1016/s0040-4039(00)60050-3
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 1,4,5,8-四甲基萘 生成 dimethyl 1,4-dihydro-1,4,5,8-tetramethyl-1,4-ethenonaphthalene-2,3-dicarboxylate
  参考文献：
  名称：

  Novel photochemistry of a sterically crowded monobenzobarrelene derivative

  摘要：

  The solution phase photochemistry of the sterically congested tetramethylated benzobarrelene derivative 2b differs completely from that of its non-methylated counterpart, 2a. Based on molecular mechanics calculations, the factor that is suggested to be responsible for this difference is relief of the unfavorable methyl-methyl interactions present in 2b.

  DOI：

  10.1016/s0040-4039(00)60050-3

文献信息

• Crystal structure and photochemistry of dimethyl 1,4-dihydro-1,4,5,8-tetramethyl-1,4-ethenonaphthalene-2,3-dicarboxylate
  作者：R. Jones、J. R. Scheffer、J. Trotter、M. Yap

  DOI：10.1107/s0108768194002594

  日期：1994.10.1

  The photochemical rearrangement of a bridgehead-methylated 1,4-ethenonaphthalene has been studied by crystal structure analyses of (1b) and two of its photoproducts (2b and 3b). Crystal data: T = 295 K, Cu K alpha, lambda = 1.54178 Angstrom, C20H22O4, M(r) = 326.39. Dimethyl 1,4-dihydro-1,4,5,8-tetramethyl-1,4-ethenonaphthalene-2,3-dicarboxylate (1b), P2(1)c, a = 12.643 (1), b = 9.288 (1), c = 15.153 (1) Angstrom, beta = 105.70 (1)degrees, Z = 4, R = 0.037 for 1974 reflections with I > 3 sigma(I). Dimethyl 2a,2b,6b,6c-tetrahydro-1,2b,3,6-tetramethylbenzo[a]cyclopropa[c,d]pentalene-6b,6c-dicarboxylate (2b), Pca2(1), a = 7.325 (1), b = 14.781 (1), c = 15.535 (1) Angstrom, Z = 4, R = 0.045 for 1419 reflections. Dimethyl 1,4,6,9-tetramethylbenzo-cyclooctatetraene-5,10-dicarboxylate (3b), Pbca, a = 17.716 (2), b = 15.298 (2), c = 13.210 (3) Angstrom, Z = 8, R = 0.046 for 2265 reflections. Molecule (1b) exhibits steric strain, as a result of short intramolecular Me...Me contacts [2.963 (5) and 3.013 (5) Angstrom]. The formation of photoproducts (2b) and (3b) can be rationalized in terms of mechanisms involving benzo-vinyl bonding, which relieves the steric crowding between methyl groups.