(2,3-dimethoxyphenoxy)acetic acid | 90296-07-4

• 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: (2,3-dimethoxyphenoxy)acetic acid
• 英文别名: (2,3-dimethoxy-phenoxy)-acetic acid；(2,3-Dimethoxy-phenoxy)-essigsaeure；2-(2,3-Dimethoxyphenoxy)acetic acid
• CAS: 90296-07-4
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: CNMADBMUSVKBQT-UHFFFAOYSA-N

物化性质

• 熔点：
  102.5-103 °C
• 沸点：
  332.2±27.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,3-dimethoxyphenoxy)acetic acid 在 aluminum (III) chloride 、 草酰氯 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 23.0h， 生成 ethyl (6-methoxy-3-oxo-2,3-dihydro-7-benzofuranoxy)acetate
  参考文献：
  名称：

  6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist

  摘要：

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.

  DOI：

  10.1021/jm400867d
• 作为产物：
  描述：

  (2,3-二甲氧基苯氧基)乙酸乙酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以90.1%的产率得到(2,3-dimethoxyphenoxy)acetic acid
  参考文献：
  名称：

  6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist

  摘要：

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.

  DOI：

  10.1021/jm400867d

文献信息

• Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids
  作者：D. J. Abraham、P. E. Kennedy、A. S. Mehanna、D. C. Patwa、F. L. Williams

  DOI：10.1021/jm00374a006

  日期：1984.8

  small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds

  在本文中，我们进一步确立了两类小分子，即苄氧基和苯氧基酸的活性，它们是血红蛋白S（HbS）凝胶化的有效抑制剂。每个类别都有大量结构修饰，这证实了我们较早的工作，即发现含有带有连接的极性侧链的二卤代芳环的化合物具有最高的活性。我们还发现卤代芳族丙二酸衍生物非常活泼。将本文报道的化合物与我们实验室研究的其他抗胶凝剂进行了比较。关于四种衍生物的抗胶凝活性和结合位点及其对血红蛋白（Hb）功能的变构机制的影响进行了评论。
• Copper-Catalyzed Regioselective Olefination and Trifluoromethylation of Carboxylic Acids To Give (<i>Z</i>)-Trifluoromethyl Enol Esters
  作者：Dong Lu、Shuangshuang Li、Xiaogang Yang、Shuang-Feng Yin、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.orglett.2c02027

  日期：2022.7.22

  Herein, we describe a method to produce (Z)-trifluoromethyl enol esters via the olefination and trifluoromethylation of carboxylic acids with TMSCF3. This synthetic method uses inexpensive and easy-to-handle TMSCF3. It employs a commercially available CuCl catalyst to transform a broad range of carboxylic acids into versatile (Z)-trifluoromethyl enol esters with good regio- and stereoselectivity. This protocol

  在此，我们描述了一种通过用 TMSCF 3对羧酸进行烯化和三氟甲基化来生产 ( Z )-三氟甲基烯醇酯的方法。这种合成方法使用廉价且易于处理的 TMSCF 3。它采用市售的 CuCl 催化剂将多种羧酸转化为具有良好区域选择性和立体选择性的多功能 ( Z )-三氟甲基烯醇酯。该协议允许直接从羧酸中简洁地合成高度功能化的 ( Z )-三氟甲基烯醇酯。
• Pfeiffer; Quehl; Tappermann, Chemische Berichte, 1930, vol. 63, p. 1301,1305
  作者：Pfeiffer、Quehl、Tappermann

  DOI：——

  日期：——
• Pfeiffer; Willems, Chemische Berichte, 1929, vol. 62, p. 1244
  作者：Pfeiffer、Willems

  DOI：——

  日期：——
• 6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist
  作者：Laura Fumagalli、Marco Pallavicini、Roberta Budriesi、Cristiano Bolchi、Mara Canovi、Alberto Chiarini、Giuseppe Chiodini、Marco Gobbi、Paola Laurino、Matteo Micucci、Valentina Straniero、Ermanno Valoti

  DOI：10.1021/jm400867d

  日期：2013.8.22

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.