methyl 2-<(2,6-dimethoxyphenyl)ethynyl>-3-methoxybenzoate | 127175-06-8

• 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: methyl 2-<(2,6-dimethoxyphenyl)ethynyl>-3-methoxybenzoate
• 英文别名: Methyl 2-((2,6-dimethoxyphenyl)ethynyl)-3-methoxybenzoate；methyl 2-[2-(2,6-dimethoxyphenyl)ethynyl]-3-methoxybenzoate
• CAS: 127175-06-8
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: ZXCPIRNNOGPRIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-<(2,6-dimethoxyphenyl)ethynyl>-3-methoxybenzoate 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以83%的产率得到2-<(2,6-dimethoxyphenyl)ethylnyl>-3-methoxybenzoic acid
  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
• 作为产物：
  描述：

  3-甲氧基水杨酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-<(2,6-dimethoxyphenyl)ethynyl>-3-methoxybenzoate
  参考文献：
  名称：

  用于分子内识别的分子。二芳基和芳基萘乙炔的合成与结构

  摘要：

  在合成用于分子内识别的模型时，开发了一种简单有效的形成末端芳基炔的方法，并使用钯催化的炔烃与芳基碘化物或芳基三氟甲磺酸酯的偶联化学形成拥挤的二取代炔烃。

  DOI：

  10.1016/s0040-4039(00)97162-4

文献信息

• EVANS, KEVIN L.;PRINCE, PHILIPPE;HUANG, ENOCH T.;BOSS, KEISHA R.;GANDOUR,+, TETRAHEDRON LETT., 31,(1990) N7, C. 6753-6756
  作者：EVANS, KEVIN L.、PRINCE, PHILIPPE、HUANG, ENOCH T.、BOSS, KEISHA R.、GANDOUR,+

  DOI：——

  日期：——
• Molecules for intramolecular recognition. Synthesis and structures of diaryl- and arylnaphthylethynes
  作者：Kevin L. Evans、Philippe Prince、Enoch T. Huang、Keisha R. Boss、Richard D. Gandour

  DOI：10.1016/s0040-4039(00)97162-4

  日期：1990.1

  While synthesizing models for intramolecular recognition, a simple and efficient method for forming terminal arylethynes was developed and palladium-catalyzed coupling chemistry of alkynes with either aryl iodides or aryl triflates was used to form crowded disubstituted alkynes.

  在合成用于分子内识别的模型时，开发了一种简单有效的形成末端芳基炔的方法，并使用钯催化的炔烃与芳基碘化物或芳基三氟甲磺酸酯的偶联化学形成拥挤的二取代炔烃。
• Lactonization Products of 2-[(2,6-Dimethoxyphenyl)ethynyl]-3-methoxybenzoic Acid
  作者：K. L. Evans、F. R. Fronczek、R. D. Gandour

  DOI：10.1107/s0108270194003124

  日期：1995.5.15

  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.