3',5'-di-t-butyl-4'-hydroxybutyrophenone | 14035-35-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',5'-di-t-butyl-4'-hydroxybutyrophenone
• 英文别名: 4-(3'-butynoyl)-2,6di-t-butylphenol；4-(3'-butynoyl)-2,6-di-tert-butylphenol；1-(3,5-Di-tert-butyl-4-hydroxyphenyl)butan-1-one；1-(3,5-ditert-butyl-4-hydroxyphenyl)butan-1-one
• CAS: 14035-35-9
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: DBEIYHSRDQQINN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  3',5'-di-t-butyl-4'-hydroxybutyrophenone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-丁基-2,6-二-叔丁基苯酚
  参考文献：
  名称：

  α-膦酰氧基烯醇化物与对醌甲基化物的非对映选择性 1,6-加成

  摘要：

  探索了在有机碱 1,8-二氮杂双环 (5.4.0)undec-7-ene (DBU) 存在下，将α-酮酰胺加入到由亚磷酸二烷基酯引发的对醌甲基化物中。在碱存在下，二烷基亚磷酸酯与 α-酮酰胺的偶联遵循 [1,2]-phospha-Brook 重排，生成相应的 α-膦酰氧基烯醇化物，随后被对醌甲基化物 ( p -QMs) 捕获。两步一锅法 1,6-缀合物添加提供了对一系列含有靛红的磷酸盐的 1,6-加合物的有效访问，这些加合物具有两个邻位叔碳，产率高达 90% 和 >20:1 dr。

  DOI：

  10.1021/acs.joc.2c00030
• 作为产物：
  描述：

  (4-butanoyl-2,6-ditert-butylphenyl) butanoate 生成 3',5'-di-t-butyl-4'-hydroxybutyrophenone
  参考文献：
  名称：

  SUDA, HIROSHI;KANOH, SHIGEYOSHI;HASEGAWA, HITOSHI;MOTOI, MASATOSHI, MET. FAC. TECHNOL. KANAZAWA UNIV., 1982, 15, N 1, 71-74

  摘要：

  DOI：

文献信息

• Monastyrskaya; Lyutkin; Gorbunov, Russian Journal of Organic Chemistry, 1997, vol. 33, # 10, p. 1409 - 1416
  作者：Monastyrskaya、Lyutkin、Gorbunov、Klimov

  DOI：——

  日期：——
• Kinetics of Rapid Internal Subgroup Rotation of a Group of Phenoxy Radicals as Studied by ENDOR Spectroscopy
  作者：Deanna C. Hurum、Robert W. Kreilick

  DOI：10.1021/j100031a004

  日期：1995.8

  Electron nuclear double resonance spectroscopy (ENDOR) has been used to study the rate of rotation of substituents at the para position of a group of phenoxy radicals. The para substituent of the molecules contain oxime groups with aliphatic substituents on the oxime carbon atom. The oxime nitrogen atom interacts with one of the phenoxy ring protons via a through space interaction. This interaction changes the electron-nuclear hyperfine coupling of this proton. Rotation of the para substituent with respect to the phenoxy ring interchanges the magnetically nonequivalent phenoxy ring protons and results in characteristic line shape changes of the ENDOR spectra from these protons. Analysis of the ENDOR Line shape allows one to determine the rate of rotation. Temperature dependence studies of rates of rotation allow one to determine activation parameters for rotation. These experiments show that the rate of rotation increases as the steric bulk of para substituent increases until the substituent becomes large enough to favor a nonplanar conformation. The ct-electron delocalization energy drives the molecules toward planar conformations which maximize delocalization of the spin into the oxime group while steric interactions between the aliphatic chains and the aromatic ring drive the molecule toward the conformation in which the oxime group is perpendicular to the ring. The activation energy for rotations is found to depend on the relative magnitude of these two types of interactions. The activation energy decreases with steric bulk until the aliphatic group is tert-butyl in which case the steric interaction is large compared to the pi-electron energy and the molecule assumes a perpendicular conformation. The activation entropy is found to be very dependant on the bulk of the substituent. These entropy changes are explained by reorganization of solvent molecules during rotation.
• US4130666A
  申请人：——

  公开号：US4130666A

  公开（公告）日：1978-12-19
• Diastereoselective 1,6-Addition of α-Phosphonyloxy Enolates to <i>para</i>-Quinone Methides
  作者：Amjad Ali、Raveena Jajoria、Harish K. Harit、Ravi P. Singh

  DOI：10.1021/acs.joc.2c00030

  日期：2022.4.15

  8-diazabicyclo(5.4.0)undec-7-ene (DBU) is explored. Coupling of dialkylphosphites to α-ketoamides in the presence of a base follows [1,2]-phospha-Brook rearrangement, generating corresponding α-phosphonyloxy enolates that are subsequently seized by p-quinone methides (p-QMs). The two-step one-pot 1,6-conjugate addition provides effective access to a series of isatin-incorporated phosphate-bearing 1,6-adducts having

  探索了在有机碱 1,8-二氮杂双环 (5.4.0)undec-7-ene (DBU) 存在下，将α-酮酰胺加入到由亚磷酸二烷基酯引发的对醌甲基化物中。在碱存在下，二烷基亚磷酸酯与 α-酮酰胺的偶联遵循 [1,2]-phospha-Brook 重排，生成相应的 α-膦酰氧基烯醇化物，随后被对醌甲基化物 ( p -QMs) 捕获。两步一锅法 1,6-缀合物添加提供了对一系列含有靛红的磷酸盐的 1,6-加合物的有效访问，这些加合物具有两个邻位叔碳，产率高达 90% 和 >20:1 dr。
• SUDA, HIROSHI;KANOH, SHIGEYOSHI;HASEGAWA, HITOSHI;MOTOI, MASATOSHI, MET. FAC. TECHNOL. KANAZAWA UNIV., 1982, 15, N 1, 71-74
  作者：SUDA, HIROSHI、KANOH, SHIGEYOSHI、HASEGAWA, HITOSHI、MOTOI, MASATOSHI

  DOI：——

  日期：——