(S)-2-(4-bromophenyl)butanoic acid | 1095322-72-7

• 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: (S)-2-(4-bromophenyl)butanoic acid
• 英文别名: (2S)-2-(4-bromophenyl)butanoic acid
• CAS: 1095322-72-7
• 化学式: C₁₀H₁₁BrO₂
• 分子量: 243.1
• InChiKey: XVEFRABIRRNWFO-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-bromophenyl)butanoic acid 、 (S)-((R)-3-(3,4-dimethoxyphenyl)-1-(3-(2-morpholinoethoxy)phenyl)propyl) piperidine-2-carboxylate 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以79 mg的产率得到(R)-3-(3,4-dimethoxyphenyl)-1-(3-(2-morpholinoethoxy)phenyl)propyl (S)-1-((S)-2-(4-bromophenyl)butanoyl)piperidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of Shld Derivatives, Their Binding to the Destabilizing Domain, and Influence on Protein Accumulation in Transgenic Plants

  摘要：

  A series of 35 analogues of Shld with modifications in the A-residue and the C-residues were prepared and investigated for binding to FKBP and GFP accumulation in transgenic plants. The modifications investigated explored variations that were supposedly inside or outside the receptor binding site with the latter being important by influencing the overall polarity of the compounds in order to improve the absorption in plants. The binding of the new compounds to the destabilizing domain was determined using a fluorescence polarization competition assay, and the GFP expression in engineered Arabidopsis thaliana was studied. The results showed that modifications of the C-building block phenol with acidic, basic, and neutral groups led to better ligands with some being better than Shld in the plant. Generally small, polar substituents showed the best GFP accumulation.

  DOI：

  10.1021/acs.jmedchem.9b00497
• 作为产物：
  描述：

  碘乙烷 、 对溴苯乙酸 在 正丁基锂 、 N¹,N³-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 以65%的产率得到(S)-2-(4-bromophenyl)butanoic acid
  参考文献：
  名称：

  以手性锂酰胺为无痕助剂的芳基乙酸的高对映选择性直接烷基化

  摘要：

  已经开发出使用容易获得的手性氨基锂作为立体定向试剂通过烯二醇对芳基乙酸进行直接、高度对映选择性的烷基化。这种方法绕过了目前用于此类转化的手性助剂的传统附着和去除。该方案操作简单，手性试剂易于回收。

  DOI：

  10.1021/ja205107x

文献信息

• Highly Enantioselective Direct Alkylation of Arylacetic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Craig E. Stivala、Armen Zakarian

  DOI：10.1021/ja205107x

  日期：2011.8.10

  A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.

  已经开发出使用容易获得的手性氨基锂作为立体定向试剂通过烯二醇对芳基乙酸进行直接、高度对映选择性的烷基化。这种方法绕过了目前用于此类转化的手性助剂的传统附着和去除。该方案操作简单，手性试剂易于回收。
• Synthesis of <b>Shld</b> Derivatives, Their Binding to the Destabilizing Domain, and Influence on Protein Accumulation in Transgenic Plants
  作者：Frederik Præstholm Jørgensen、Daniel Madsen、Morten Meldal、Jacob Valdbjørn Olsen、Morten Petersen、Jeppe Granhøj、Mikael Bols

  DOI：10.1021/acs.jmedchem.9b00497

  日期：2019.5.23

  A series of 35 analogues of Shld with modifications in the A-residue and the C-residues were prepared and investigated for binding to FKBP and GFP accumulation in transgenic plants. The modifications investigated explored variations that were supposedly inside or outside the receptor binding site with the latter being important by influencing the overall polarity of the compounds in order to improve the absorption in plants. The binding of the new compounds to the destabilizing domain was determined using a fluorescence polarization competition assay, and the GFP expression in engineered Arabidopsis thaliana was studied. The results showed that modifications of the C-building block phenol with acidic, basic, and neutral groups led to better ligands with some being better than Shld in the plant. Generally small, polar substituents showed the best GFP accumulation.