1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one | 143729-91-3

• 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: 1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one
• CAS: 143729-91-3
• 化学式: C₂₁H₂₁NO₅S
• 分子量: 399.467
• InChiKey: RIZCZAVZIBEVPK-YZGWKJHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one 在 草酰氯 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 10.75h， 生成 5(R)-<(benzyloxy)methyl>-4(S)-<(S)-α-methoxyphenylacetoxy>-3(R)-p-toluenesulfonamidocyclopent-1-ene
  参考文献：
  名称：

  A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations

  摘要：

  A new class of ligands for asymmetric transition metal catalysis based on 2-(diphenylphosphino)benzoic acid was used in a mechanistically-defined palladium-catalyzed reaction in which enantiodifferentiation was the result of selective ionization of substrates derived from cis-2-cycloalkene-1,4-diols. By making rational, stepwise changes in the ligand structure, the structural requirements for good asymmetric induction were probed. The absolute stereochemistry of the products was found to be related to the chirality of the ligand in a predictable fashion. A mnemonic is given which allows one to predict the mode of ionization (R or S) solely on the basis of the stereochemistry of the variable chiral linker used to make the ligand.

  DOI：

  10.1021/ja00050a013
• 作为产物：
  描述：

  (1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol 、 对甲基苯磺酰异氰酸酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 (S,S)-ANDEN-Phenyl Trost Ligand 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-4S-<(benzyloxy)methyl>-1-<(4'-methylphenyl)sulfonyl>cyclopent-5-eno<4,5-d>-3aR,6aS-1,3-oxazolidinone 、 1-(p-tolylsulfonyl)-4(S)-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-(3aR,6aS)-oxazolidin-2-one
  参考文献：
  名称：

  A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations

  摘要：

  A new class of ligands for asymmetric transition metal catalysis based on 2-(diphenylphosphino)benzoic acid was used in a mechanistically-defined palladium-catalyzed reaction in which enantiodifferentiation was the result of selective ionization of substrates derived from cis-2-cycloalkene-1,4-diols. By making rational, stepwise changes in the ligand structure, the structural requirements for good asymmetric induction were probed. The absolute stereochemistry of the products was found to be related to the chirality of the ligand in a predictable fashion. A mnemonic is given which allows one to predict the mode of ionization (R or S) solely on the basis of the stereochemistry of the variable chiral linker used to make the ligand.

  DOI：

  10.1021/ja00050a013