(Z)-3-<(2,6-dimethoxyphenyl)methylene>-4-methoxy-1(3H)-isobenzofuranone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (Z)-3-<(2,6-dimethoxyphenyl)methylene>-4-methoxy-1(3H)-isobenzofuranone
• 英文别名: 3-(2,6-Dimethoxybenzylidene)-4-methoxy-2-benzofuran-1(3H)-one；(3Z)-3-[(2,6-dimethoxyphenyl)methylidene]-4-methoxy-2-benzofuran-1-one
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: QWVIZGZSFKXYGN-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-<(2,6-dimethoxyphenyl)ethylnyl>-3-methoxybenzoic acid 以62%的产率得到(Z)-3-<(2,6-dimethoxyphenyl)methylene>-4-methoxy-1(3H)-isobenzofuranone
  参考文献：
  名称：

  Lactonization Products of 2-[(2,6-Dimethoxyphenyl)ethynyl]-3-methoxybenzoic Acid

  摘要：

  Structural analyses of 2-[(2,6-dimethoxyphenyl)ethynyl]3-methoxybenzoic acid, (1), and the two products of lactonization, 3-(2,6-dimethoxyphenyl)-5-methoxy-1H-2-benzopyran-1-one, (2), and (Z)-3-[(2,6-dimethoxyphenyl)methylene] -4-methoxy-1(3H)-isobenzofuranone, (3), three isomers of C18H16O5, suggest an explanation for the favored pathway for lactonization. The two rings in (1) form a dihedral angle of 84.30 (4)degrees. The carboxy group is nearly coplanar with the benzoate ring with an O=C-C-C torsion angle of -3.7 (2)degrees. The triple-bond length is 1.191 (2) Angstrom and the bond angles at the ethynyl C atoms are 176.4 (1) and 171.0 (1)degrees, both significantly distorted from 180 degrees. The benzopyran ring and the dimethoxyphenyl ring in (2) form a dihedral angle of 58.90 (5)degrees. The pyrano C=C double-bond length is 1.324 (2) Angstrom. Distortions appear in the two exocyclic angles [112.1 (1) and 127.3 (2)degrees] about the aryl substituted pyrano C atom. The isobenzofuran ring and the dimethoxyphenyl ring in (3) form a dihedral angle of 120.83 (5)degrees. The exocyclic C=C double-bond length is 1.323 (2) Angstrom. Distortions appear in the benzenoid angles at the C atoms adjacent to the ring fusion [117.5 (1) and 116.7 (1)degrees] and in two of the three angles [121.2 (1), 131.00 (9) and 107.7 (1)degrees] about the furano C atom of the exocyclic C=C double bond.

  DOI：

  10.1107/s0108270194003124