(R)-(-)-2-(1-hydroxyethyl)ethyl-5-methylvalerophenone | 343266-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(-)-2-(1-hydroxyethyl)ethyl-5-methylvalerophenone
• 英文别名: 1-[2-[(2R)-4-hydroxybutan-2-yl]-5-methylphenyl]pentan-1-one
• CAS: 343266-72-8
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: TYMZSVIYBDSYLK-CYBMUJFWSA-N

物化性质

• 沸点：
  387.3±30.0 °C(predicted)
• 密度：
  0.990±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-(1-hydroxyethyl)ethyl-5-methylvalerophenone 在 三氟过氧乙酸 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 反应 1.08h， 以31%的产率得到(-)-2-(1-hydroxyethyl)ethyl-5-methylphenol
  参考文献：
  名称：

  Novel Sparteine-Mediated Enantio-Dichotomic Formal Synthesis of (R)-(−)- and (S)-(+)-Curcuphenol

  摘要：

  High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e), The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.

  DOI：

  10.1021/jo001485c
• 作为产物：
  描述：

  2,5-二甲基苯甲酸 在 正丁基锂 、 氯化亚砜 、 四甲基乙二胺 、 仲丁基锂 、 臭氧 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 环己烷 、 正戊烷 为溶剂， 反应 25.5h， 生成 (R)-(-)-2-(1-hydroxyethyl)ethyl-5-methylvalerophenone
  参考文献：
  名称：

  Novel Sparteine-Mediated Enantio-Dichotomic Formal Synthesis of (R)-(−)- and (S)-(+)-Curcuphenol

  摘要：

  High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e), The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.

  DOI：

  10.1021/jo001485c

文献信息

• Novel Sparteine-Mediated Enantio-Dichotomic Formal Synthesis of (<i>R</i>)-(−)- and (<i>S</i>)-(+)-Curcuphenol
  作者：Tetsutaro Kimachi、Yoshiji Takemoto

  DOI：10.1021/jo001485c

  日期：2001.4.1

  High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e), The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.