2-[(2,3-二甲氧基苯基)甲基]苯甲酸 | 87567-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(2,3-二甲氧基苯基)甲基]苯甲酸
• 英文名称: 2-((2,3-dimethoxyphenyl)methyl)benzoic acid
• 英文别名: 2-(2',3'-dimethoxybenzyl)benzoic acid；2-[(2,3-Dimethoxyphenyl)methyl]benzoic acid
• CAS: 87567-78-0
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: BRMPRODTZDSJQT-UHFFFAOYSA-N

物化性质

• 沸点：
  413.4±35.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2,3-二甲氧基苯基)甲基]苯甲酸 在 硫酸 作用下， 反应 0.33h， 生成 2,3-dimethoxy-9-anthrone
  参考文献：
  名称：

  光化学转化。35. 电子从光激发芳香环转移到碳-氯键的立体化学。光-Wagner-Meerwein 重排中迁移的合成立体化学

  摘要：

  对苯并萘并双环 (2.2.2) 辛二烯和苯并萘并双环 (2.2.2) 辛二烯的异构 7,8-二氯衍生物的基态和激发态溶剂分解进行了研究。正如预期的那样，银离子辅助的基态反应继续进行，在 Wagner-Meerwein 重排的溶剂分解产物中反映了干净的反立体化学（迁移终点的反转）。与之前报道的观察结果不同，从光激发的苯环到 ..β..-碳-氯键的激发转移需要反立体化学，从激发的萘或藜芦醇环的电子转移发生在顺式和反碳-氯键上，尽管后者是首选。结果与给出两性离子双自由基的电子转移过程一致，并由 Weller 方程合理化。从假定的两性离子双自由基中分离氯离子伴随着“Wagner-Meerwein”重排，但主要是顺式，而不是基态中的反式。重排立体化学与以下观点一致，即在主要的光化学过程中，保留构型的迁移与氯离子的损失相一致。3桌。在主要的光化学过程中，保留构型的迁移与氯离子的损失相一致。3桌。在主要

  DOI：

  10.1021/ja00363a022
• 作为产物：
  描述：

  4,4-二甲基-2-苯基-2-噁唑啉 在 palladium on activated charcoal 盐酸 、 氢气 、 仲丁基锂 、 溶剂黄146 作用下， 25.0~80.0 ℃ 、344.73 kPa 条件下， 反应 22.0h， 生成 2-[(2,3-二甲氧基苯基)甲基]苯甲酸
  参考文献：
  名称：

  Synthesis and Evaluation of 6,7-Dihydroxy-2,3,4,8,9,13b-hexahydro-1H-benzo[6,7]cyclohepta[1,2,3-ef][3]benzazepine, 6,7-Dihydroxy-1,2,3,4,8,12b-hexahydroanthr[10,4a,4-cd]azepine, and 10-(Aminomethyl)-9,10-dihydro-1,2-dihydroxyanthracene as Conformationally Restricted Analogs of .beta.-Phenyldopamine

  摘要：

  The present study was designed to define the geometry of the hydrophobic accessory region for binding of dopamine Dr receptor ligands and to assess the relative importance of ethylamine side chain conformation for receptor affinity. Three compounds, 6,7-dihydroxy-2,3,4,8,9,13b-hexahydro-1H-benzo[6,7]cyclohepta[1,2,3-ef][3]benzazepine, 4, 6,7-dihydroxy-1,2,3,4,8,12b-hexahydroanthr[10,4a,4-cd]azepine, 5, and 10-(aminomethyl)-9,10-dihydro-1 2-dihydroxyanthracene, 6, were synthesized as conformationally restricted analogs of beta-phenyldopamine. Molecular modeling studies were performed to compare these three compounds with the high-affinity D-1 agonists dihydrexidine (DHX), 2, and SKF 38393, 3. The beta-phenyl moieties in the target compounds are constrained by means of either an ethyl (4) or methylene (5 and 6) bridge. The compounds adopt minimum-energy conformations in which the beta-phenyl group is approximately -22 degrees (4), -12 degrees (5), and -30 degrees (6) from coplanarity with the catechol ring. These compounds also embody either a freely rotating (6) or a rigidified gauche (4 and 5) rotameric conformation of the dopamine ethylamine side chain, the latter nearly perfectly superimposible on the benzazepine portion of SKF 38393. Radioligand competition experiments showed that compounds 4, 5, and 6 have only micromolar affinity for both the D-1 and D-2 dopamine receptor subtypes. The low affinity of 4-6, relative to 2 and 3, may be due to improper orientation of the beta-phenyl moiety and provides important information about the three-dimensional orientation of the hydrophobic accessory binding domain of the dopamine D-1 receptor. In addition, the negligible affinity of 6, as compared to 2 and 3, indicates that the rotameric positioning of the ethylamine side chain may not be a primary determinant of receptor affinity.

  DOI：

  10.1021/jm00013a015

文献信息

• Photochemical transformations. 35. Stereochemistry of electron transfer from photoexcited aromatic rings to carbon-chlorine bonds. Syn stereochemistry of migration in photo-Wagner-Meerwein rearrangements
  作者：Stanley J. Cristol、Dave G. Seapy、Ellen O. Aeling

  DOI：10.1021/ja00363a022

  日期：1983.11

  and are rationalized by the Weller equation. Separation of chloride ion from the presumed zwitterionic biradical is accompanied by ''Wagner-Meerwein'' rearrangement but is predominately syn, rather than anti as in the ground state. The rearrangement stereochemistry is consistent with the idea that, in the principal photochemical process, migration with retention of configuration is concerted with the

  对苯并萘并双环 (2.2.2) 辛二烯和苯并萘并双环 (2.2.2) 辛二烯的异构 7,8-二氯衍生物的基态和激发态溶剂分解进行了研究。正如预期的那样，银离子辅助的基态反应继续进行，在 Wagner-Meerwein 重排的溶剂分解产物中反映了干净的反立体化学（迁移终点的反转）。与之前报道的观察结果不同，从光激发的苯环到 ..β..-碳-氯键的激发转移需要反立体化学，从激发的萘或藜芦醇环的电子转移发生在顺式和反碳-氯键上，尽管后者是首选。结果与给出两性离子双自由基的电子转移过程一致，并由 Weller 方程合理化。从假定的两性离子双自由基中分离氯离子伴随着“Wagner-Meerwein”重排，但主要是顺式，而不是基态中的反式。重排立体化学与以下观点一致，即在主要的光化学过程中，保留构型的迁移与氯离子的损失相一致。3桌。在主要的光化学过程中，保留构型的迁移与氯离子的损失相一致。3桌。在主要
• Synthesis and Evaluation of 6,7-Dihydroxy-2,3,4,8,9,13b-hexahydro-1H-benzo[6,7]cyclohepta[1,2,3-ef][3]benzazepine, 6,7-Dihydroxy-1,2,3,4,8,12b-hexahydroanthr[10,4a,4-cd]azepine, and 10-(Aminomethyl)-9,10-dihydro-1,2-dihydroxyanthracene as Conformationally Restricted Analogs of .beta.-Phenyldopamine
  作者：Scott E. Snyder、Felix A. Aviles-Garay、Ratna Chakraborti、David E. Nichols、Val J. Watts、Richard B. Mailman

  DOI：10.1021/jm00013a015

  日期：1995.6

  The present study was designed to define the geometry of the hydrophobic accessory region for binding of dopamine Dr receptor ligands and to assess the relative importance of ethylamine side chain conformation for receptor affinity. Three compounds, 6,7-dihydroxy-2,3,4,8,9,13b-hexahydro-1H-benzo[6,7]cyclohepta[1,2,3-ef][3]benzazepine, 4, 6,7-dihydroxy-1,2,3,4,8,12b-hexahydroanthr[10,4a,4-cd]azepine, 5, and 10-(aminomethyl)-9,10-dihydro-1 2-dihydroxyanthracene, 6, were synthesized as conformationally restricted analogs of beta-phenyldopamine. Molecular modeling studies were performed to compare these three compounds with the high-affinity D-1 agonists dihydrexidine (DHX), 2, and SKF 38393, 3. The beta-phenyl moieties in the target compounds are constrained by means of either an ethyl (4) or methylene (5 and 6) bridge. The compounds adopt minimum-energy conformations in which the beta-phenyl group is approximately -22 degrees (4), -12 degrees (5), and -30 degrees (6) from coplanarity with the catechol ring. These compounds also embody either a freely rotating (6) or a rigidified gauche (4 and 5) rotameric conformation of the dopamine ethylamine side chain, the latter nearly perfectly superimposible on the benzazepine portion of SKF 38393. Radioligand competition experiments showed that compounds 4, 5, and 6 have only micromolar affinity for both the D-1 and D-2 dopamine receptor subtypes. The low affinity of 4-6, relative to 2 and 3, may be due to improper orientation of the beta-phenyl moiety and provides important information about the three-dimensional orientation of the hydrophobic accessory binding domain of the dopamine D-1 receptor. In addition, the negligible affinity of 6, as compared to 2 and 3, indicates that the rotameric positioning of the ethylamine side chain may not be a primary determinant of receptor affinity.