2-[4-(heptyloxy)phenyl]acetic acid | 29148-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[4-(heptyloxy)phenyl]acetic acid
• 英文别名: <4-n-Heptyloxy-phenyl>-essigsaeure；4-n-Heptoxyphenylessigsaeure；[4-(Heptyloxy)phenyl]acetic acid；2-(4-heptoxyphenyl)acetic acid
• CAS: 29148-13-8
• 化学式: C₁₅H₂₂O₃
• mdl: MFCD09925061
• 分子量: 250.338
• InChiKey: YQEHHHRXVUMHDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  385.8±17.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[4-(heptyloxy)phenyl]acetic acid 生成 (2-ethoxy-2-oxoethyl) 2-(4-heptoxyphenyl)acetate
  参考文献：
  名称：

  TEHRAO, SINDZI;XIRATA, MINORU

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-[4-(heptyloxy)phenyl]acetic acid
  参考文献：
  名称：

  发现以烷氧基取代的苯乙酸为核心的新型醛糖还原酶抑制剂

  摘要：

  为了继续我们旨在开发新型醛糖还原酶抑制剂的努力，制备并筛选了几种分别在 3 位或 4 位带有烷氧基取代基的苯乙酸。后者代表了我们小组最近详细阐述的环己基甲氧基苯乙酸 IIa 和 IIb 的正式开环产物。在这些系列中，以正庚氧基亚基为特征的化合物 4aa 和 4ba 被证明是最有效的抑制剂。基于这些出乎意料的结果，我们建议这种烷基侧链可以作为 4-溴-2-氟苄基残基的有用替代物，这些残基通常存在于强效醛糖还原酶抑制剂中。

  DOI：

  10.1002/ardp.200600054

文献信息

• Amphipathic benzoic acid derivatives: Synthesis and binding in the hydrophobic tunnel of the zinc deacetylase LpxC
  作者：Hyunshun Shin、Heather A. Gennadios、Douglas A. Whittington、David W. Christianson

  DOI：10.1016/j.bmc.2007.01.044

  日期：2007.4

  The first committed step in lipid A biosynthesis is catalyzed by uridine diphosphate-(3-O-(R-3-hydroxymyristoyl))--Nacetylglucosamine deacetylase (LpxC), a zinc-dependent deacetylase, and inhibitors of LpxC may be useful in the development of antibacterial agents targeting a broad spectrum of Gram-negative bacteria. Here, we report the design of amphipathic benzoic acid derivatives that bind in the hydrophobic tunnel in the active site of LpxC. The hydrophobic tunnel accounts for the specificity of LpxC toward substrates and substrate andlogues bearing a 3-O-myristoyl substituent. Simple benzoic acid derivatives bearing an aliphatic 'tail' bind in the hydrophobic tunnel with micromolar affinity despite the lack of a glucosamine ring like that of the substrate. However, although these benzoic acid derivatives each contain a negatively charged carboxylate 'warhead' intended to coordinate to the active site zinc ion, the 2.25 angstrom resolution X-ray crystal structure of LpxC complexed with 3-(heptyloxy)benzoate reveals 'backward' binding in the hydrophobic tunnel, such that the benzoate moiety does not coordinate to zinc. Instead, it binds at the outer end of the hydrophobic tunnel. Interestingly, these ligands bind with affinities comparable to those measured for more complicated substrate analogue inhibitors containing glucosamine ring analogues and hydroxamate 'warheads' that coordinate to the active site zinc ion. We conclude that the intermolecular interactions in the hydrophobic tunnel dominate enzyme affinity in this series of benzoic acid derivatives. Published by Elsevier Ltd.
• Stilbene derivatives. New class of room temperature nematic liquids
  作者：William R. Young、Arieh Aviram、Robert J. Cox

  DOI：10.1021/ja00766a054

  日期：1972.5
• ZASCHKE H.; ARNDT S.; WAGNER V.; SCHUBERT H., Z. CHEM., 1977, 17, HO 8, 293-294
  作者：ZASCHKE H.、 ARNDT S.、 WAGNER V.、 SCHUBERT H.

  DOI：——

  日期：——
• Discovery of Novel Aldose Reductase Inhibitors Characterized by an Alkoxy-Substituted Phenylacetic Acid Core
  作者：Dietmar Rakowitz、Andreas Gmeiner、Barbara Matuszczak

  DOI：10.1002/ardp.200600054

  日期：2006.10

  towards the development of novel aldose reductase inhibitors, several phenylacetic acids bearing an alkoxy substituent in position 3 or 4, respectively, were prepared and screened. The latter represent formal ring opening products of the cyclohexylmethyloxyphenylacetic acids IIa and IIb, recently elaborated in our group. Out of these series, compounds 4aa and 4ba characterized by an n‐heptyloxy subunit

  为了继续我们旨在开发新型醛糖还原酶抑制剂的努力，制备并筛选了几种分别在 3 位或 4 位带有烷氧基取代基的苯乙酸。后者代表了我们小组最近详细阐述的环己基甲氧基苯乙酸 IIa 和 IIb 的正式开环产物。在这些系列中，以正庚氧基亚基为特征的化合物 4aa 和 4ba 被证明是最有效的抑制剂。基于这些出乎意料的结果，我们建议这种烷基侧链可以作为 4-溴-2-氟苄基残基的有用替代物，这些残基通常存在于强效醛糖还原酶抑制剂中。
• TEHRAO, SINDZI;XIRATA, MINORU
  作者：TEHRAO, SINDZI、XIRATA, MINORU

  DOI：——

  日期：——