(S)-(+)-2-(hydroxymethyl)-3,3dimethylcyclobutanone | 875008-32-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-2-(hydroxymethyl)-3,3dimethylcyclobutanone
• 英文别名: (2S)-2-(hydroxymethyl)-3,3-dimethylcyclobutan-1-one
• CAS: 875008-32-5
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: SMRLVCYMGBNOJQ-YFKPBYRVSA-N

物化性质

• 沸点：
  205.1±13.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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-(hydroxymethyl)-3,3dimethylcyclobutanone 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以72%的产率得到(+)-(S)-5-(hydroxymethyl)-4,4-dimethyldihydrofuran-2-(3H)-one
  参考文献：
  名称：

  Enantiomeric resolution of cyclobutanones and related derivatives by enzyme-catalyzed acylation and hydrolysis

  摘要：

  A method for the regio- and enantioselective protection and deprotection of a number of cyclobutanone derivatives employing the isolated enzyme porcine pancreatic lipase (PPL) has been developed. PPL catalyzes the regioselective acylation or deacylation of the C-3 substituent in (2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutanone and its enantiomer. Photochemical ring expansion of the corresponding cyclobutanones in methanol gave anomeric mixtures of the methyl furanosides with stereochemical retention of the ring substituents. The PPL-catalyzed hydrolysis of the acetal derived from (2S,3R)-bis[acetoxymethyl]cyclobutanone resulted in a regioselective reaction of the C-3 acetoxymethyl group. PPL exhibits no hydrolysis activity toward the acetal derived from the enantiomeric cyclobutanone diacetate.Racemic 2-acetoxymethyl-3,3-dimethylcyclobutanone was converted to its enantiomerically enriched (S)-alcohol by PPL-catalyzed hydrolysis. The corresponding methyl furanoside obtained from the photochemical ring expansion of racemic 2-acetoxymethyl-3,3-dimethylcyclobutanone in methanol is not an effective substrate for PPL mediated hydrolysis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.043
• 作为产物：
  描述：

  梨醇酯 在 phosphate buffer 、 porcine pancreatic lipase 、 溶剂黄146 、 锌 作用下， 以 乙二醇二甲醚 、 乙醚 、 甲苯 为溶剂， 反应 20.0h， 生成 (S)-(+)-2-(hydroxymethyl)-3,3dimethylcyclobutanone
  参考文献：
  名称：

  Enantiomeric resolution of cyclobutanones and related derivatives by enzyme-catalyzed acylation and hydrolysis

  摘要：

  A method for the regio- and enantioselective protection and deprotection of a number of cyclobutanone derivatives employing the isolated enzyme porcine pancreatic lipase (PPL) has been developed. PPL catalyzes the regioselective acylation or deacylation of the C-3 substituent in (2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutanone and its enantiomer. Photochemical ring expansion of the corresponding cyclobutanones in methanol gave anomeric mixtures of the methyl furanosides with stereochemical retention of the ring substituents. The PPL-catalyzed hydrolysis of the acetal derived from (2S,3R)-bis[acetoxymethyl]cyclobutanone resulted in a regioselective reaction of the C-3 acetoxymethyl group. PPL exhibits no hydrolysis activity toward the acetal derived from the enantiomeric cyclobutanone diacetate.Racemic 2-acetoxymethyl-3,3-dimethylcyclobutanone was converted to its enantiomerically enriched (S)-alcohol by PPL-catalyzed hydrolysis. The corresponding methyl furanoside obtained from the photochemical ring expansion of racemic 2-acetoxymethyl-3,3-dimethylcyclobutanone in methanol is not an effective substrate for PPL mediated hydrolysis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.043

文献信息

• Enantiomeric resolution of cyclobutanones and related derivatives by enzyme-catalyzed acylation and hydrolysis
  作者：Reza Salezadeh-Asl、Edward Lee-Ruff

  DOI：10.1016/j.tetasy.2005.10.043

  日期：2005.12

  A method for the regio- and enantioselective protection and deprotection of a number of cyclobutanone derivatives employing the isolated enzyme porcine pancreatic lipase (PPL) has been developed. PPL catalyzes the regioselective acylation or deacylation of the C-3 substituent in (2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutanone and its enantiomer. Photochemical ring expansion of the corresponding cyclobutanones in methanol gave anomeric mixtures of the methyl furanosides with stereochemical retention of the ring substituents. The PPL-catalyzed hydrolysis of the acetal derived from (2S,3R)-bis[acetoxymethyl]cyclobutanone resulted in a regioselective reaction of the C-3 acetoxymethyl group. PPL exhibits no hydrolysis activity toward the acetal derived from the enantiomeric cyclobutanone diacetate.Racemic 2-acetoxymethyl-3,3-dimethylcyclobutanone was converted to its enantiomerically enriched (S)-alcohol by PPL-catalyzed hydrolysis. The corresponding methyl furanoside obtained from the photochemical ring expansion of racemic 2-acetoxymethyl-3,3-dimethylcyclobutanone in methanol is not an effective substrate for PPL mediated hydrolysis. (c) 2005 Elsevier Ltd. All rights reserved.