cis (±)-1-methyl-2-phenylcyclopropane-1,2-dicarboxylic acid | 718-86-5

• 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: cis (±)-1-methyl-2-phenylcyclopropane-1,2-dicarboxylic acid
• 英文别名: (+/-)-1-Methyl-2t-phenyl-cyclopropan-1r.2c-dicarbonsaeure；cis-1-Phenyl-2-methyl-1,2-dicarboxy-cyclopropan；1,2-Cyclopropanedicarboxylic acid, 1-methyl-2-phenyl-；(1R,2R)-1-methyl-2-phenylcyclopropane-1,2-dicarboxylic acid
• CAS: 718-86-5；718-87-6；91963-67-6
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: WXLQMEREIOUYBW-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis (±)-1-methyl-2-phenylcyclopropane-1,2-dicarboxylic acid 以62%的产率得到
  参考文献：
  名称：

  TAKAKI KEN; NEGORO KENJI; AGAWA TOSHIO, J. CHEM. SOC. PERKIN TRANS., 1979, PART 1, NO 6, 1490-1493

  摘要：

  DOI：
• 作为产物：
  描述：

  cis (±)-diethyl 1-methyl-2-phenylcyclopropane-1,2-dicarboxylate 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以69%的产率得到cis (±)-1-methyl-2-phenylcyclopropane-1,2-dicarboxylic acid
  参考文献：
  名称：

  Cyclopropane-1,2-dicarboxylic acids as new tools for the biophysical investigation ofO-acetylserine sulfhydrylases by fluorimetric methods and saturation transfer difference (STD) NMR

  摘要：

  Cysteine is a building block for many biomolecules that are crucial for living organisms. O-Acetylserine sulfhydrylase (OASS), present in bacteria and plants but absent in mammals, catalyzes the last step of cysteine biosynthesis. This enzyme has been deeply investigated because, beside the biosynthesis of cysteine, it exerts a series of "moonlighting" activities in bacteria. We have previously reported a series of molecules capable of inhibiting Salmonella typhimurium (S. typhymurium) OASS isoforms at nanomolar concentrations, using a combination of computational and spectroscopic approaches. The cyclopropane-1,2-dicarboxylic acids presented herein provide further insights into the binding mode of small molecules to OASS enzymes. Saturation transfer difference NMR (STD-NMR) was used to characterize the molecule/ enzyme interactions for both OASS-A and B. Most of the compounds induce a several fold increase in fluorescence emission of the pyridoxal 5'-phosphate (PLP) coenzyme upon binding to either OASS-A or OASS-B, making these compounds excellent tools for the development of competition-binding experiments.

  DOI：

  10.1080/14756366.2016.1218486

文献信息

• Three Membered Rings. II. The Stereochemistry of Formation of Some 1,1,2,2-Tetrasubstituted Cyclopropanes
  作者：LAYTON L. McCOY

  DOI：10.1021/jo01082a002

  日期：1960.12