(3E)-4-(4-methoxyphenyl)-pent-3-enoic acid | 689259-20-9

• 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: (3E)-4-(4-methoxyphenyl)-pent-3-enoic acid
• 英文别名: (E)-4-(4-methoxyphenyl)pent-3-enoic acid
• CAS: 689259-20-9
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: SGIBYOLEAWNLFS-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (3E)-4-(4-methoxyphenyl)-pent-3-enoic acid 在 (Sa,S)-[(C8H12)Ir(P(3,5-(methyl)2C6H3)2C8H7CC8H7C3NOH3(α-naphthylmethyl))][tetrakis[3,5-bis(trifluoromethyl)phenyl]borate] 、 氢气 、 三乙胺 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 65.0 ℃ 、303.99 kPa 条件下， 反应 12.0h， 以96%的产率得到(-)-4-(4-methoxyphenyl)pentanoic acid
  参考文献：
  名称：

  β，γ-不饱和羧酸对映体铱催化的加氢：手性4-烷基-4-芳基丁酸的有效方法

  摘要：

  手性酸：为制备手性的4-烷基-4-芳基丁酸，开发了一种高度对映选择性的铱催化的β，γ-不饱和羧酸加氢反应（参见方案）。

  DOI：

  10.1002/anie.201107802
• 作为产物：
  描述：

  丙二酸 、 2-(4-甲氧基苯基)丙醛 在 三乙胺 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 以64%的产率得到(3E)-4-(4-methoxyphenyl)-pent-3-enoic acid
  参考文献：
  名称：

  β，γ-不饱和羧酸对映体铱催化的加氢：手性4-烷基-4-芳基丁酸的有效方法

  摘要：

  手性酸：为制备手性的4-烷基-4-芳基丁酸，开发了一种高度对映选择性的铱催化的β，γ-不饱和羧酸加氢反应（参见方案）。

  DOI：

  10.1002/anie.201107802

文献信息

• Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
  申请人：——

  公开号：US20040092538A1

  公开（公告）日：2004-05-13

  The present invention relates to a class of compounds represented by the Formula I 1 or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the &agr; v &bgr; 3 and/or &agr; v &bgr; 5 integrin.

  本发明涉及一类由公式I代表的化合物 1 或其药用可接受的盐，包含公式I化合物的药物组合物，以及选择性地抑制或拮抗α v β 3 和/或α v β 5 整合素的方法。
• An Approach to Enantioselective 5-endo Halo-Lactonization Reactions
  作者：Jean Marc Garnier、Sylvie Robin、Gérard Rousseau

  DOI：10.1002/ejoc.200700041

  日期：2007.7

  Enantioselective lactonization of 4-substituted but-3-enoic acids using iodobis(N-methylephedrine) hexafluoroantimonate in dichloromethane at low temperatures is reported. The presence of bis(N-methylephedrine)silver(I) hexafluoroantimonate, derived from the excess amounts of N-methylephedrine and silver hexafluoroantimonate that were necessary for the generation of the iodo complex in the reaction

  据报道，在低温下，在二氯甲烷中使用碘双（N-甲基麻黄碱）六氟锑酸盐对 4-取代的丁-3-烯酸进行对映选择性内酯化。双（N-甲基麻黄碱）银（I）六氟锑酸盐的存在，源自过量的 N-甲基麻黄碱和六氟锑酸银，这是反应混合物中生成碘络合物所必需的，对于该反应的成功至关重要. 已经检查了这些环化反应的不同参数。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Discovery of +(2-{4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}-cyclopropyl)acetic acid as potent and selective αvβ3 inhibitor: Design, synthesis, and optimization
  作者：Srinivasan R. Nagarajan、Hwang-Fun Lu、Alan F. Gasiecki、Ish K. Khanna、Mihir D. Parikh、Bipinchandra N. Desai、Thomas E. Rogers、Michael Clare、Barbara B. Chen、Mark A. Russell、Jeffery L. Keene、Tiffany Duffin、V. Wayne Engleman、Mary B. Finn、Sandra K. Freeman、Jon A. Klover、G. Alan Nickols、Maureen A. Nickols、Kristen E. Shannon、Christina A. Steininger、William F. Westlin、Marisa M. Westlin、Melanie L. Williams

  DOI：10.1016/j.bmc.2007.03.020

  日期：2007.5

  The integrin alpha(v)beta(3) is expressed in a number of cell types and is thought to play a major role in several pathological conditions. Various small molecules that inhibit the integrin have been shown to suppress tumor growth and retinal angiogenesis. The tripeptide Arg-Gly-Asp (RGD), a common binding motif in several ligands that bind to alpha(v)beta(3), has been depeptidized and optimized in our efforts toward discovering a small molecule inhibitor. We recently disclosed the synthesis and biological activity of several small molecules that did not contain any peptide bond and mimic the tripeptide RGD. The phenethyl group in one of the lead compounds was successfully replaced with a cyclopropyl moiety. The new lead compound was optimized for potency, selectivity, and for its ADME properties. We describe herein the discovery, synthesis, and optimization of cyclopropyl containing analogs that are potent and selective inhibitors of alpha(v)beta(3). (c) 2007 Elsevier Ltd. All rights reserved.
• Tandem hydroboration/reduction of trisubstituted β,γ-unsaturated esters for the asymmetric synthesis of chiral 1,3-diols
  作者：Paul S. Fordred、Steven D. Bull

  DOI：10.1016/j.tetlet.2012.10.047

  日期：2013.1

  Treatment of a range of trisubstituted beta,gamma-unsaturated esters with 2 equiv of (-)-monoisopinocampheylborane results in hydroboration of their alkene functionalities and reduction of their ester groups to afford chiral 1,3-diols containing two new vicinal beta,gamma-(anti)-stereocentres in 67-85% enantiomeric excess. (C) 2012 Elsevier Ltd. All rights reserved.
• US6921767B2
  申请人：——

  公开号：US6921767B2

  公开（公告）日：2005-07-26