2-(3,5-二甲氧基苯氧基)乙酸乙酯 | 115109-77-8

• 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-(3,5-二甲氧基苯氧基)乙酸乙酯
• 英文名称: (3,5-dimethoxyphenoxy)acetic acid ethyl ester
• 英文别名: Acetic acid, (3,5-dimethoxyphenoxy)-, ethyl ester；ethyl 2-(3,5-dimethoxyphenoxy)acetate
• CAS: 115109-77-8
• 化学式: C₁₂H₁₆O₅
• mdl: MFCD11646639
• 分子量: 240.256
• InChiKey: GEGZNXPSKSOPMI-UHFFFAOYSA-N

物化性质

• 沸点：
  344.0±27.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 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：

  2-(3,5-二甲氧基苯氧基)乙酸乙酯 在 sodium hydroxide 、 水 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2-(3,5-二甲氧基苯氧基)乙酸
  参考文献：
  名称：

  Synthesis and Insect Antifeedant Activity of Aurones against Spodoptera litura Larvae

  摘要：

  A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 mu mol/cm(2). The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED(50)) and a hydrogen-bonding parameter calculated from the R-f value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.

  DOI：

  10.1021/jf062562t
• 作为产物：
  描述：

  3,5-二甲氧基苯酚 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以78%的产率得到2-(3,5-二甲氧基苯氧基)乙酸乙酯
  参考文献：
  名称：

  钯催化的芳基烯烃/烯烃的羰基化环化：合成电子丰富的色氨酸的新反应模式

  摘要：

  据报道，Pd（II）催化的芳基烯烃和芳基烯醇的分子内羰基化环化反应可合成结构多样的苯并二氢吡喃。在CO的球囊压力下，将PdCl 2（CH 3 CN）2用作催化剂，将CuCl 2用作氧化剂。反应在温和的条件下进行，并且可以在高区域和高纯度下生成苯并二氢吡喃型酯和内酯。立体选择性的方式。

  DOI：

  10.1021/acs.orglett.5b00214

文献信息

• Novel benzo-fused heterocycles as endothelin antagonisits
  申请人：Bolli Martin

  公开号：US20050124605A1

  公开（公告）日：2005-06-09

  The invention relates to novel benzo-fused heterocycles and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.

  本发明涉及新型苯并杂环化合物及其用作制备药物组成物的活性成分。本发明还涉及相关方面，包括制备化合物的过程，含有其中一种或多种化合物的药物组成物，特别是它们作为内皮素受体拮抗剂的用途。
• Novel Benzo[1,4]diazepin-2-one Derivatives as Endothelin Receptor Antagonists
  作者：Martin H. Bolli、Judith Marfurt、Corinna Grisostomi、Christoph Boss、Christoph Binkert、Patrick Hess、Alexander Treiber、Eric Thorin、Keith Morrison、Stephan Buchmann、Daniel Bur、Henri Ramuz、Martine Clozel、Walter Fischli、Thomas Weller

  DOI：10.1021/jm031115r

  日期：2004.5.1

  Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan 2, are in late clinical trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan 2, we designed a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e] [1,4]diazepin-2-one scaffold. Here, we report on the preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives. Potent dual ETA/ETB receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt sensitive rats. In this animal model, the efficacy of the benzo [e] [1,4] diazepin-2-one derivative rac-39au was superior to that of racemic ambrisentan, rac-2.
• Thuillie,G., Chimica Therapeutica, 1966, vol. 1, p. 82 - 86
  作者：Thuillie,G.

  DOI：——

  日期：——
• US7238685B2
  申请人：——

  公开号：US7238685B2

  公开（公告）日：2007-07-03
• [EN] NOVEL BENZO-FUSED HETEROCYCLES AS ENDOTHELIN ANTAGONISITS<br/>[FR] HETEROCYCLES A FUSION BENZO UTILISES COMME ANTAGONISTES VIS-A-VIS DE L'ENDOTHELINE
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2003013545A1

  公开（公告）日：2003-02-20

  The invention relates to novel benzo-fused heterocycles of structure (I) and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists. Formula (I)