4-[2-(1-hydroxy-1-methyl-ethyl)-4-isopropyl-phenyl]-4-oxo-butyric acid, methyl ester | 1210050-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2-(1-hydroxy-1-methyl-ethyl)-4-isopropyl-phenyl]-4-oxo-butyric acid, methyl ester
• 英文别名: Methyl 4-[2-(2-hydroxypropan-2-yl)-4-propan-2-ylphenyl]-4-oxobutanoate
• CAS: 1210050-46-6
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: JQVUWEQFBJGKRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(2,4-diisopropylphenyl)-4-oxobutanoic acid methyl ester 在 氧气 作用下， 以 二氯甲烷 为溶剂， 以1.5 mg的产率得到4-[2-(1-hydroxy-1-methyl-ethyl)-4-isopropyl-phenyl]-4-oxo-butyric acid, methyl ester
  参考文献：
  名称：

  Effect of Alkyl Substituents on Photorelease from Butyrophenone Derivatives

  摘要：

  Photolysis of 1a yields 4a in organ-saturated methanol, whereas 1b is photostable. Laser flash photolysis of 1a in acetonitrile shows formation of biradical 2a (lambda(max) = 380 nm, tau = similar to 60 ns), which undergoes intersystem crossing to form Z-3a (lambda(max) = 380 nm, tau = 270 ns) and E-3a (lambda(max) = 380 nm, tau = 300 ms). Z-3a regenerates the starting material, whereas E-3b undergoes intramolecular lactonization to release the alcohol moiety and form 4a. Similar laser flash photolysis of 1b shows formation of biradical 2b (lambda(max) = 340 nm, tau = 1.9 mu s in acetonitrile), which is longer-lived than 2a is. However, 2b only undergoes intersystem crossing to form Z-3b (lambda(max) = 380 nm, tau = 4.3 mu s). Calculations demonstrate that intramolecular pseudo hydrogen bonding between the OH moiety and the radical centered on the isopropyl carbon in 2b and the bulkiness of the isopropyl group prevent the necessary rotation to form E-3b. In comparison, 2a does not form an intramolecular pseudo hydrogen bond between the methylene radical center and the OH group, and as a consequence, it undergoes intersystem crossing to form both E- and Z-3a.

  DOI：

  10.1021/jo9021088