(S)-(+)-2-hydroxycyclobutanone dimethyl acetal | 737758-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-2-hydroxycyclobutanone dimethyl acetal
• 英文别名: (1S)-2,2-dimethoxycyclobutan-1-ol
• CAS: 737758-82-6
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: AGUUATVSVNTRQD-YFKPBYRVSA-N

物化性质

• 沸点：
  169.2±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 (S)-(+)-2-hydroxycyclobutanone dimethyl acetal 在 4-二甲氨基吡啶 N,N'-二环己基碳二亚胺 作用下， 生成 (S)-(-)-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
• 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