4-羟基-2-氧杂螺[4.5]癸烷-3-酮 | 100144-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 4-羟基-2-氧杂螺[4.5]癸烷-3-酮
• 英文名称: 4-hydroxy-2-oxaspiro[4.5]decan-3-one
• 英文别名: 4-hydroxy-2-oxa-spiro[4.5]decan-3-one；α-Hydroxy-1-(hydroxymethyl)-cyclohexanessigsaeure-lacton
• CAS: 100144-82-9
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: OOGYDVXOZPLMGG-UHFFFAOYSA-N

物化性质

• 沸点：
  328.4±17.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-羟基-2-氧杂螺[4.5]癸烷-3-酮 、 苯胺 在 对甲苯磺酸 作用下， 反应 1.83h， 以46%的产率得到4-hydroxy-2-phenyl-2-azaspiro[4.5]decan-3-one
  参考文献：
  名称：

  Silylation-Based Kinetic Resolution of α-Hydroxy Lactones and Lactams

  摘要：

  A silylation-based kinetic resolution has been developed for alpha-hydroxy lactones and lactams employing the chiral isothiourea catalyst (-)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams, and selectivity factors up to 100 can be achieved utilizing commercially available reagents.

  DOI：

  10.1021/ol402982w
• 作为产物：
  描述：

  在 盐酸 、 sodium tetrahydroborate 、 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 4-羟基-2-氧杂螺[4.5]癸烷-3-酮
  参考文献：
  名称：

  Silylation-Based Kinetic Resolution of α-Hydroxy Lactones and Lactams

  摘要：

  A silylation-based kinetic resolution has been developed for alpha-hydroxy lactones and lactams employing the chiral isothiourea catalyst (-)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams, and selectivity factors up to 100 can be achieved utilizing commercially available reagents.

  DOI：

  10.1021/ol402982w

文献信息

• Silylation-Based Kinetic Resolution of α-Hydroxy Lactones and Lactams
  作者：Robert W. Clark、T. Maxwell Deaton、Yan Zhang、Maggie I. Moore、Sheryl L. Wiskur

  DOI：10.1021/ol402982w

  日期：2013.12.20

  A silylation-based kinetic resolution has been developed for alpha-hydroxy lactones and lactams employing the chiral isothiourea catalyst (-)-benzotetramisole and triphenylsilyl chloride as the silyl source. The system is more selective for lactones than lactams, and selectivity factors up to 100 can be achieved utilizing commercially available reagents.