[(1S)-1-methyl-2-oxocyclopentyl]methyl 2-[diethoxy(oxido)phosphaniumyl]acetate | 1246858-53-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: [(1S)-1-methyl-2-oxocyclopentyl]methyl 2-[diethoxy(oxido)phosphaniumyl]acetate
• CAS: 1246858-53-6
• 化学式: C₁₃H₂₃O₆P
• 分子量: 306.296
• InChiKey: PBEIJPRNGWXZCH-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1S)-1-methyl-2-oxocyclopentyl]methyl 2-[diethoxy(oxido)phosphaniumyl]acetate 在 三乙胺 、 lithium bromide 作用下， 生成 (7aR)-7a-methyl-1,5,6,7-tetrahydrocyclopenta[c]pyran-3-one
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones

  摘要：

  The resolution of alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 and cyclohexanones 3 has been efficiently achieved by using lipase-catalyzed transesterification reactions with vinyl acetate as the acylating agent. The enantiomeric selectivities were dependent on both the ring size of the cycloalkanone and the bulk of the carbon group located at the stereogenic quaternary center. The resolved alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 were used as enantiopure (or enantioenriched) precursors for the synthesis of the optically active pseudoiridolactones 6-7. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.043
• 作为产物：
  描述：

  二乙基磷乙酸 、 (S)-2-hydroxymethyl-2-methylcyclopentanone 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 [(1S)-1-methyl-2-oxocyclopentyl]methyl 2-[diethoxy(oxido)phosphaniumyl]acetate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones

  摘要：

  The resolution of alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 and cyclohexanones 3 has been efficiently achieved by using lipase-catalyzed transesterification reactions with vinyl acetate as the acylating agent. The enantiomeric selectivities were dependent on both the ring size of the cycloalkanone and the bulk of the carbon group located at the stereogenic quaternary center. The resolved alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 were used as enantiopure (or enantioenriched) precursors for the synthesis of the optically active pseudoiridolactones 6-7. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.043

文献信息

• Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones
  作者：Zineb Guerrab、Stefan Schweiger、Boujemâa Daou、Mohammed Ahmar、Bernard Cazes

  DOI：10.1016/j.tetasy.2010.04.043

  日期：2010.7

  The resolution of alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 and cyclohexanones 3 has been efficiently achieved by using lipase-catalyzed transesterification reactions with vinyl acetate as the acylating agent. The enantiomeric selectivities were dependent on both the ring size of the cycloalkanone and the bulk of the carbon group located at the stereogenic quaternary center. The resolved alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 were used as enantiopure (or enantioenriched) precursors for the synthesis of the optically active pseudoiridolactones 6-7. (C) 2010 Elsevier Ltd. All rights reserved.