2-Carboxymethylphenyl-benzyl-sulfoxid | 62331-90-2

• 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: 2-Carboxymethylphenyl-benzyl-sulfoxid
• 英文别名: o-Benzylsulfinyl-benzoesaeuremethylester；o-(benzylsulfinyl)methylbenzoate；methyl (2-benzylsulfinyl)benzoate；Methyl 2-(phenylmethanesulfinyl)benzoate；methyl 2-benzylsulfinylbenzoate
• CAS: 62331-90-2
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: MLXPREWDKMMTKO-UHFFFAOYSA-N

物化性质

• 沸点：
  471.6±38.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Carboxymethylphenyl-benzyl-sulfoxid 、 Phenol, 2,4,6-trinitro-, lanthanum(3+) salt 以 乙醇 为溶剂， 以99%的产率得到La(pic)3*2.5(BSMB)
  参考文献：
  名称：

  Synthesis, characterization and spectroscopy of lanthanide picrate complexes with o-(benzylsulfinyl)methylbenzoate

  摘要：

  Complexes of the general formula (Ln(pic)(3)(.)2.5(BSMB) (Ln=La, Ce, Nd, Sm, Eu, Tb and Er; pic=picrate, BSMB=o-(benzylsulfinyl)methylbenzoate) were prepared. The characterization of the ligand and complexes were carried out by CHN elemental analyses, lanthanide titration with EDTA, IR absorption spectroscopy, conductance measurements and emission spectroscopy (for the Eu and Sm adducts). Conductance measurements, indicate a non electrolyte behavior. The SO stretching mode is shifted to lower energies, with respect to the neat ligand, evidencing coordination through the SO group. IR data also suggest that the picrate anions are bidentate, coordinated though the phenolic and one o-nitrogroup oxygens. The transition 5D(o) --> F-5(0,1,2) for europium and (4)G(5/2) --> (6)G(5/2.7/2.9/2) for samarium with broad, non-resolved peaks, yield evidence of the polymeric nature of these complexes. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0925-8388(02)00312-2
• 作为产物：
  描述：

  methyl 2-(benzylthio)benzoate 在 间氯过氧苯甲酸 作用下， 生成 2-Carboxymethylphenyl-benzyl-sulfoxid
  参考文献：
  名称：

  手性钛催化剂存在下对芳基苄硫醚的对映选择性氧化理论与实验研究

  摘要：

  在钛/氢安息香催化剂存在下，叔丁基氢过氧化物对芳基苄基硫醚的对映选择性氧化的实验研究表明，这些硫化物是该催化体系的理想底物，芳基上的取代基对干扰的影响可忽略不计。提出了一种基于DFT计算的反应机理。DFT MPWB1K官能团用于理论研究中，以解决弱氢键和π相互作用的问题。所计算的反应曲线说明了实验观察到的对映选择性，这是由反应第一阶段的热力学确定的。给出了沿着观察到的立体化学路径推动反应的氢键和π相互作用的详细讨论。

  DOI：

  10.1002/chem.200902110

文献信息

• Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
  作者：Giulia Rotondi、Paolo Guglielmi、Simone Carradori、Daniela Secci、Celeste De Monte、Barbara De Filippis、Cristina Maccallini、Rosa Amoroso、Roberto Cirilli、Atilla Akdemir、Andrea Angeli、Claudiu T. Supuran

  DOI：10.1080/14756366.2019.1651315

  日期：2019.1.1

  Abstract A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range

  抽象的 合成了大量基于2-（苄基亚磺酰基）苯甲酸支架的衍生物库，并作为针对人碳酸酐酶的四种不同同工型的非典型抑制剂进行了测试（hCA I，II，IX和XII，EC 4.2.1.1）。对主要官能团周围的化学空间的探索导致发现了微摩尔/纳摩尔范围内的选择性hCA IX抑制剂，从而在这种多功能支架内建立了稳固的结构-活性关系。进行了一些选定手性化合物的HPLC分离和相应对映异构体的生物学评估，并对活性最高的衍生物进行了分子建模研究。
• JANCZEWSKI, M.;MAJEWSKI, W.;RADKIEWICZ, S.;GRZEGORSKI, S., ANN. UMCS, 1982, 37, 1-17
  作者：JANCZEWSKI, M.、MAJEWSKI, W.、RADKIEWICZ, S.、GRZEGORSKI, S.

  DOI：——

  日期：——
• Synthesis, characterization and spectroscopy of lanthanide picrate complexes with o-(benzylsulfinyl)methylbenzoate
  作者：K. Umeda、P.C. Isolani、M.H. Zaim、G. Vicentini

  DOI：10.1016/s0925-8388(02)00312-2

  日期：2002.10

  Complexes of the general formula (Ln(pic)(3)(.)2.5(BSMB) (Ln=La, Ce, Nd, Sm, Eu, Tb and Er; pic=picrate, BSMB=o-(benzylsulfinyl)methylbenzoate) were prepared. The characterization of the ligand and complexes were carried out by CHN elemental analyses, lanthanide titration with EDTA, IR absorption spectroscopy, conductance measurements and emission spectroscopy (for the Eu and Sm adducts). Conductance measurements, indicate a non electrolyte behavior. The SO stretching mode is shifted to lower energies, with respect to the neat ligand, evidencing coordination through the SO group. IR data also suggest that the picrate anions are bidentate, coordinated though the phenolic and one o-nitrogroup oxygens. The transition 5D(o) --> F-5(0,1,2) for europium and (4)G(5/2) --> (6)G(5/2.7/2.9/2) for samarium with broad, non-resolved peaks, yield evidence of the polymeric nature of these complexes. (C) 2002 Elsevier Science B.V. All rights reserved.
• A Combined Theoretical and Experimental Investigation on the Enantioselective Oxidation of Aryl Benzyl Sulfides in the Presence of a Chiral Titanium Catalyst
  作者：Francesco Naso、Maria Annunziata M. Capozzi、Andrea Bottoni、Matteo Calvaresi、Valerio Bertolasi、Francesco Capitelli、Cosimo Cardellicchio

  DOI：10.1002/chem.200902110

  日期：2009.12.14

  An experimental investigation of the enantioselective oxidation of aryl benzyl sulfides by tert‐butyl hydroperoxide in the presence of a titanium/hydrobenzoin catalyst has shown that these sulfides are ideal substrates for this catalytic system, with negligible interference by the substituents on the aryl groups. A reaction mechanism based on DFT computations has been proposed. The DFT MPWB1K functional

  在钛/氢安息香催化剂存在下，叔丁基氢过氧化物对芳基苄基硫醚的对映选择性氧化的实验研究表明，这些硫化物是该催化体系的理想底物，芳基上的取代基对干扰的影响可忽略不计。提出了一种基于DFT计算的反应机理。DFT MPWB1K官能团用于理论研究中，以解决弱氢键和π相互作用的问题。所计算的反应曲线说明了实验观察到的对映选择性，这是由反应第一阶段的热力学确定的。给出了沿着观察到的立体化学路径推动反应的氢键和π相互作用的详细讨论。