3-(2,6-二甲基苯基)丙酸 | 192725-73-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 3-(2,6-二甲基苯基)丙酸
• 英文名称: 3-(2',6'-dimethylphenyl)propionic acid
• 英文别名: 3-(2,6-dimethylphenyl)-propanoic acid；3-(2,6-dimethylphenyl)propanoic Acid
• CAS: 192725-73-8
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: CMUMYLYPFFNWNN-UHFFFAOYSA-N

物化性质

• 沸点：
  311.9±11.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  3-(2,6-二甲基苯基)丙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  可见光诱导的 C(sp2)-H 酰胺化与芳基-烷基 σ-键重定位通过氧化还原-中性自由基-极性交叉

  摘要：

  在此，已开发出N-苯甲酰氧基酰胺的光催化分子内 C(sp 2 )-H 酰胺化，以提供具有芳基-烷基σ -键重定位的δ -苯内酰胺。一旦经由还原N-O键断裂形成酰胺基的基团，选择性自由基本位-addition接着是氧化还原中性基极交叉建议负责优先C-C键的迁移。

  DOI：

  10.1002/anie.202108775
• 作为产物：
  描述：

  2,6-二甲基苯甲醛 在 palladium on activated charcoal lithium hydroxide 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 3-(2,6-二甲基苯基)丙酸
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a novel series of HIV-1 protease inhibitors encompassing ABT-378 (Lopinavir)

  摘要：

  The HIV protease inhibitor ABT-378 (Lopinavir) has a 2,6-dimethylphenoxyacetyl group in the P-2' position. Analogues in which this group is replaced with various substituted phenyl or heteroaryl groups were synthesized and the Structure-activity relationships explored. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00134-8

文献信息

• Retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：EP1170289A2

  公开（公告）日：2002-01-09

  A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

  披露了一种包含公式（II）取代基的化合物，作为一种HIV蛋白酶抑制剂。还披露了用于制造此类化合物的中间体以及制造此类中间体的过程。
• Iron-Catalyzed Asymmetric Decarboxylative Azidation
  作者：Kaikai Wang、Yajun Li、Xiaoyan Li、Daliang Li、Hongli Bao

  DOI：10.1021/acs.orglett.1c03355

  日期：2021.11.19

  The first iron-catalyzed asymmetric azidation of benzylic peresters has been reported with trimethylsilyl azide (TMSN3) as the azido source. Hydrocarbon radicals that lack of strong interactions were capable to be enantioselectively azidated. The reaction features good functional group tolerance, high yields, and mild conditions. The chiral benzylic azides can further be used in click reaction, phosphoramidation

  已经报道了以三甲基甲硅烷基叠氮化物 (TMSN 3 ) 作为叠氮源的第一次铁催化的苄基过酸酯的不对称叠氮化。缺乏强相互作用的烃基能够被对映选择性叠氮化。该反应具有官能团耐受性好、产率高、条件温和等特点。手性苄基叠氮化物可进一步用于点击反应、磷酰胺化和还原胺化，这证明了该反应的合成价值。
• Rhodium(I)-Catalyzed 1,4-Addition of Arylboronic Acids to Acrylic Acid in Water: One-Step Preparation of 3-Arylpropionic Acids
  作者：Bernhard Breit、Nicolas Vautravers

  DOI：10.1055/s-0030-1260319

  日期：2011.10

  A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium.

  报告了一种通过铑催化芳基硼酸与丙烯酸的 1,4- 加成一步制备 3-芳基丙酸的实用方法。该方法适用于多种芳基硼酸，在以水为最佳反应介质的条件下，具有广泛的官能团耐受性。
• 2‘,6‘-Dimethylphenoxyacetyl:  A New Achiral High Affinity P₃-P₂ Ligand for Peptidomimetic-Based HIV Protease Inhibitors
  作者：Pierre L. Beaulieu、Paul C. Anderson、Dale R. Cameron、Gilbert Croteau、Vida Gorys、Chantal Grand-Maître、Daniel Lamarre、Francine Liard、William Paris、Louis Plamondon、François Soucy、Diane Thibeault、Dominik Wernic、Christiane Yoakim、Susan Pav、Liang Tong

  DOI：10.1021/jm990336n

  日期：2000.3.1

  Starting from palinavir (1), our lead HIV protease inhibitor, we have discovered a new series of truncated analogues in which the P-3-P-2 quinaldic-valine portion of 1 was replaced by 2',6'-dimethylphenoxyacetyl. With EC50's in the 1-2 nM range, some of these compounds are among the most potent inhibitors of HIV replication in vitro, reported to date. One of the most promising members in this series (compound 27, BILA 2185 BS) exhibited a favorable overall pharmacokinetic profile, with 61% apparent oral bioavailability in rat. X-ray crystal structures and molecular modeling were used to rationalize the high potency resulting from incorporation of this structurally simple, achiral ligand into the P-3-P-2 position of hydroxyethylamine-based HIV protease inhibitors.
• Cross-Coupling of Remote <i>meta</i>-C–H Bonds Directed by a U-Shaped Template
  作者：Li Wan、Navid Dastbaravardeh、Gang Li、Jin-Quan Yu

  DOI：10.1021/ja410760f

  日期：2013.12.4

  meta-C-H arylation and methylation of 3-phenylpropanoic acid and phenolic derivatives were developed using an easily removable nitrile template. The combination of a weakly coordinating U-shaped template and mono-protected amino acid ligand was crucial for the cross-coupling of C-H bonds with organoborons.