1-(m-Methoxymesityl)-2,2-dimesitylethenol | 118042-68-5

• 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: 1-(m-Methoxymesityl)-2,2-dimesitylethenol
• 英文别名: 1-(3-methoxy-2,4,6-trimethylphenyl)-2,2-bis(2,4,6-trimethylphenyl)ethenol
• CAS: 118042-68-5
• 化学式: C₃₀H₃₆O₂
• 分子量: 428.615
• InChiKey: XLQRSUPCUYGBBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(m-Methoxymesityl)-2,2-dimesitylethenol 以70%的产率得到
  参考文献：
  名称：

  Rochlin Elimelech, Rappoport Zvi, J. Org. Chem, 59 (1994) N 14, S 3857-3870

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(mesityl)ketene 、 1-Bromo-3-methoxy-2,4,6-trimethylbenzene 在 magnesium 作用下， 生成 1-(m-Methoxymesityl)-2,2-dimesitylethenol
  参考文献：
  名称：

  Biali, Silvio E.; Rappoport, Zvi; Mannschreck, Albrecht, Angewandte Chemie, 1989, vol. 101, # 2, p. 202 - 203

  摘要：

  DOI：

文献信息

• Mapping the Enantiomerization Routes of Triarylvinyl Propellers. Barriers to the Three-Ring Flip and the Three Different Two-Ring Flips of m-Methoxy-Substituted Trimesitylvinyl Isopropyl Ethers
  作者：Elimelech Rochlin、Zvi Rappoport

  DOI：10.1021/jo00093a018

  日期：1994.7

  E- and Z-(m-methoxymesityl)-1,2-dimesitylethenols (3a and 4a), their isopropyl ethers 3c and 4c, and 1-(m-methoxymesityl)-2,2-dimesitylvinyl isopropyl ether (2c) were prepared. X-ray structures of 3a and 3c were determined. The rotational barriers for the 3-ring flips are 18.8 (3a) and 18.3 (4a) kcal mol(-1). Each of 2c-4c display two MeO singlets and four i-Pr doublets and exist as a mixture of two pairs of enantiomers differing in helicity and in the ''up'' and ''down'' disposition of the OMe in relation to the C=C bond. The threshold process for correlated rotation around the Ar-C bonds of 2c-4c is a three-ring flip which leads to diastereomerization with helicity reversal, with barriers of 15.8-16.1 kcal mol(-1) resembling that for the three-ring flip enantiomerization of trimesitylvinyl isopropyl ether. The DNMR at the i-Pr region showed two coalescence processes. The lower barrier is for a three-ring flip diastereomerization, and the higher barrier is for the two-ring flip enantiomerization of the residual isomers where the MeO-labeled ring passes via the C=C plane. The barriers for the beta,beta'-, alpha,beta-, and alpha,beta' two-ring flips are 25.2 (2c), 23.1 (4c), and 21.1 (3c) kcal mol(-1). RIM calculations on the ground-state conformation are in reasonable agreement with the X-ray data, but in the calculated transition states the rings are distorted and the barriers differ from the observed ones. When ring planarity and o-Me group constraints are imposed, an agreement of the calculated and observed barriers is achieved. The conformation of the i-Pr group significantly affects the calculated barrier. The order of the barriers for the isomeric two-ring nip processes is ascribed mainly to different steric interactions between neighboring rings in the isomeric transition states.