S-tert-butyl (R)-3-hydroxy-3-(4-methoxyphenyl)butanethioate | 1070240-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: S-tert-butyl (R)-3-hydroxy-3-(4-methoxyphenyl)butanethioate
• 英文别名: S-tert-butyl (3R)-3-hydroxy-3-(4-methoxyphenyl)butanethioate
• CAS: 1070240-81-1
• 化学式: C₁₅H₂₂O₃S
• 分子量: 282.404
• InChiKey: ULUAJAPYANCQTD-OAHLLOKOSA-N

物化性质

• 沸点：
  412.8±45.0 °C(predicted)
• 密度：
  1.108±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酮 、 1-(tert-butylthio)-1-diphenylsilyloxyethene 在 [(1S)-1-[(4S)-3-(4-methylphenyl)sulfonyl-5-oxo-2-phenyl-1,3,2-oxazaborolidin-4-yl]ethyl] benzoate 、 盐酸 作用下， 以 甲苯 、 四氢呋喃 、 水 为溶剂， 反应 51.0h， 生成 S-tert-butyl (R)-3-hydroxy-3-(4-methoxyphenyl)butanethioate 、 S-tert-butyl (S)-3-hydroxy-3-(4-methoxyphenyl)butanethioate
  参考文献：
  名称：

  Asymmetric Mukaiyama Aldol Reaction of Nonactivated Ketones Catalyzed by allo-Threonine-Derived Oxazaborolidinone

  摘要：

  Asymmetric Mukaiyama aldol reaction of nonactivated ketones is realized for the first time by using an oxazaborolidinone catalyst derived from O-benzoyl-N-tosyl-allo-threonine. By employing a dimethylsilyl ketene S,O-acetal as a nucleophile, a variety of acetophenone derivatives afford the corresponding tertiary beta-hydroxy carbonyl compounds with high enantioselectivity up to 98% ee.

  DOI：

  10.1021/ol802087u

文献信息

• Asymmetric Mukaiyama Aldol Reaction of Nonactivated Ketones Catalyzed by <i>allo</i>-Threonine-Derived Oxazaborolidinone
  作者：Shinya Adachi、Toshiro Harada

  DOI：10.1021/ol802087u

  日期：2008.11.6

  Asymmetric Mukaiyama aldol reaction of nonactivated ketones is realized for the first time by using an oxazaborolidinone catalyst derived from O-benzoyl-N-tosyl-allo-threonine. By employing a dimethylsilyl ketene S,O-acetal as a nucleophile, a variety of acetophenone derivatives afford the corresponding tertiary beta-hydroxy carbonyl compounds with high enantioselectivity up to 98% ee.