(1S,2S)-2-o-toluamide-1-phenyl-1,3-O-isopropylidenepropane | 927268-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-2-o-toluamide-1-phenyl-1,3-O-isopropylidenepropane
• 英文别名: N-[(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl]-2-methylbenzamide
• CAS: 927268-50-6
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: JJBDMZWHUDQAMA-ROUUACIJSA-N

物化性质

• 熔点：
  108-111 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  488.2±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-o-toluamide-1-phenyl-1,3-O-isopropylidenepropane 、 6,7-二甲氧基-3,4-二氢异喹啉 在 正丁基锂 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Addition Reaction of o-Toluamides with Chiral Auxiliary Derived from 2-Amino-1,3-propanediols to Imines

  摘要：

  Stereoselectivity of the addition reaction of o-toluamides, incorporating 2-amino-1,3-propanediols as chiral auxiliary to imines has been studied. Addition products, diastercomerically enriched, after column chromatography separation were obtained and further transformed to (S)-(-)-or (R)-(+)-8-oxoberbines with ee up to 97%.

  DOI：

  10.3987/com-06-s(o)34
• 作为产物：
  描述：

  (1S,2S)-2-o-toluamide-1-[4-(methylthio)phenyl]-1,3-O-isopropylidene-1,3-propanediol 在 镍 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以75%的产率得到(1S,2S)-2-o-toluamide-1-phenyl-1,3-O-isopropylidenepropane
  参考文献：
  名称：

  Addition Reaction of o-Toluamides with Chiral Auxiliary Derived from 2-Amino-1,3-propanediols to Imines

  摘要：

  Stereoselectivity of the addition reaction of o-toluamides, incorporating 2-amino-1,3-propanediols as chiral auxiliary to imines has been studied. Addition products, diastercomerically enriched, after column chromatography separation were obtained and further transformed to (S)-(-)-or (R)-(+)-8-oxoberbines with ee up to 97%.

  DOI：

  10.3987/com-06-s(o)34

文献信息

• Addition Reaction of o-Toluamides with Chiral Auxiliary Derived from 2-Amino-1,3-propanediols to Imines
  作者：Maria Chrzanowska、Agnieszka Dreas

  DOI：10.3987/com-06-s(o)34

  日期：——

  Stereoselectivity of the addition reaction of o-toluamides, incorporating 2-amino-1,3-propanediols as chiral auxiliary to imines has been studied. Addition products, diastercomerically enriched, after column chromatography separation were obtained and further transformed to (S)-(-)-or (R)-(+)-8-oxoberbines with ee up to 97%.