(R)-(+)-2-acetoxycyclobutanone dimethyl acetal | 737758-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(+)-2-acetoxycyclobutanone dimethyl acetal
• 英文别名: [(1R)-2,2-dimethoxycyclobutyl] acetate
• CAS: 737758-84-8
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: PCLLBTTWLSVKRB-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-acetoxycyclobutanone dimethyl acetal 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (R)-(-)-2-benzyloxycyclobutanone dimethyl acetal
  参考文献：
  名称：

  The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode

  摘要：

  A new practical enzymatic synthesis of (R)-(+)- and (S)-(-)-2-acetoxycyclobutanone acetals with 97-99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-hydroxycyclobutanone acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)- (-)-2- benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.016
• 作为产物：
  描述：

  乙酸乙烯酯 、 (+/-)-2-hydroxycyclobutanone dimethyl acetal 在 Candida antarctica lipase B immobilized on acrylic resin 作用下， 以 正己烷 为溶剂， 反应 78.0h， 以42%的产率得到(R)-(+)-2-acetoxycyclobutanone dimethyl acetal
  参考文献：
  名称：

  The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode

  摘要：

  A new practical enzymatic synthesis of (R)-(+)- and (S)-(-)-2-acetoxycyclobutanone acetals with 97-99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-hydroxycyclobutanone acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)- (-)-2- benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.016