(4-tert-butyl-2,6-dimethylphenyl)mesitylacetic acid | 91110-65-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4-tert-butyl-2,6-dimethylphenyl)mesitylacetic acid
• CAS: 91110-65-5
• 化学式: C₂₃H₃₀O₂
• 分子量: 338.49
• InChiKey: MLPLGAUPOUCHMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4-tert-butyl-2,6-dimethylphenyl)mesitylacetic acid 在 吡啶 、 氯化亚砜 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 (4-tert-butyl-2,6-dimethylphenyl)mesitylketene
  参考文献：
  名称：

  Stable simple enols. 5. Solvent dependence of the conformation of the OH group in 2,2-dimesitylethenol and several 1,2,2-triarylethenols

  摘要：

  DOI：

  10.1021/ja00331a039
• 作为产物：
  描述：

  1-叔丁基-3,5-二甲苯 、 2,4,6-trimethylmandelic acid 在 四氯化锡 作用下， 反应 16.0h， 以80%的产率得到(4-tert-butyl-2,6-dimethylphenyl)mesitylacetic acid
  参考文献：
  名称：

  Stable simple enols. 5. Solvent dependence of the conformation of the OH group in 2,2-dimesitylethenol and several 1,2,2-triarylethenols

  摘要：

  DOI：

  10.1021/ja00331a039

文献信息

• Does the Threshold Enantiomerization Route of Crowded Tetraarylethenes Involve Double Bond Rotation?
  作者：Katsuhiro Maeda、Yoshio Okamoto、Natalia Morlender、Nizar Haddad、Irina Eventova、Silvio E. Biali、Zvi Rappoport

  DOI：10.1021/ja00143a010

  日期：1995.9

  The chiral tetraarylvinyl propeller 1,2-bis(4-tert-butyl-2,6-dimethylphenyl)-1,2-dimesitylethene (4) was synthesized by irradiation of (4-tert-butyl-2,6-dimethylphenyl)mesitylketene 5. Ethene 4 exists in two diastereomeric forms (E and Z), each existing as a racemate (i.e., (+)/(-) 4Z and (+)/(-) 4E). The enantiomers were resolved by chiral HPLC and the E/Z diastereomers were separated by (achiral) supercritical fluid chromatography. The enantiomerization process which was studied in n-pentadecane has a barrier of Delta G double dagger = 44.8 +/- 0.7 kcal mol(-1). A 4Z reversible arrow 4E interconversion was not observed under the enantiomerization conditions. Consequently, we conclude that the threshold enantiomerization process of 4 does not involve a double bond rotation. A lower limit of 48.7 kcal mol(-1) is estimated for the barrier of the latter rotation.