1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropan-1-one | 14035-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropan-1-one
• 英文别名: 1-(3,5-di-t-butyl-4-hydroxyphenyl)-2-methylpropan-1-one；1-(3,5-ditert-butyl-4-hydroxyphenyl)-2-methylpropan-1-one
• CAS: 14035-36-0
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: JIYZTMSNFPZJGR-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147°C

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  4
• 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：

  1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以70%的产率得到2,6-di-tert-butyl-4-(1-hydroxy-2-methylpropyl)phenol
  参考文献：
  名称：

  Oxidation of bisphenols. II. Some compounds related to galvinoxyl

  摘要：

  一系列 4,4'-亚烷基双（2,6-二叔丁基苯酚 研究了一系列 4,4'-亚烷基双（2,6-二叔丁基苯酚）的氧化反应。 考察了一系列 4,4'-亚烷基双（2,6-二对丁基苯酚）的氧化过程。在 在单取代的化合物中，单苯氧基自由基的稳定性随着取代基大小的增加而增加。 随着取代基大小的增加，单苯氧基自由基的稳定性增加，而半乙酰氧基自由基的稳定性降低。β-偶联产物 只从亚乙基双酚中获得，这一结果与 e.s.r. 超频分裂常数相关联。随着单取代基或双取代基的增加，双螺过氧化物成为首选的 氧化产物。描述了乙烯-双丙烯酰氧基双环氧乙烷的 e.s.r. 光谱。 双环氧乙烷的 e.s.r. 光谱。

  DOI：

  10.1071/ch9800351
• 作为产物：
  描述：

  2,6-Di-tert-butyl-4-(1-hydroxy-1-isopropyl-2-methyl-propyl)-phenol 在 Co(Salpr) 、 氧气 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.17h， 生成 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropan-1-one
  参考文献：
  名称：

  Oxygenation of tert-butylphenols with an unsaturated side chain

  摘要：

  DOI：

  10.1021/jo00362a018

文献信息

• Oxygenation of 2,6-di-t-butylphenols bearing electron-withdrawing group at 4-position mediated by Co(II)-schiff base complex
  作者：A. Nishinaga、T. Shimizu、T. Matsuura

  DOI：10.1016/s0040-4039(01)92484-0

  日期：——

  4-Acyl-2,6-di-t-butylphenols except 3,5-di-t-butyl-4-hydroxybenzaldehyde were oxygenated in the presence of Co(Salpr) exclusively at the ortho position to give the corresponding 3,5-di-t-butyl-6-hydroperoxy-2,4-cyclohexadienone derivatives in quantitative yield.

  在Co（Salpr）存在的情况下，仅在邻位将3,5-二叔丁基-4-羟基苯甲醛之外的4-酰基-2,6-二叔丁基苯酚氧化，得到相应的3,5-二叔丁基-6-氢过氧-2,4-环己二酮衍生物的定量收率。
• Oxidation of bisphenols. II. Some compounds related to galvinoxyl
  作者：SM Colegate、FR Hewgill

  DOI：10.1071/ch9800351

  日期：——

  The oxidation of a series of 4,4'-alkylidenebis(2,6-di-t-butylphenols) having increasing substitution of the central methylene carbon by alkyl groups is examined. In the monosubstituted compounds the stability of the monophenoxy radical increases with increase in the size of the substituent, while the stability of the galvinoxyl type radical decreases. β-Coupled products are only obtained from the ethylidene bisphenol, a result that can be correlated with e.s.r. hyperfine splitting constants. With increasing mono- or di-substitution bisspiroperoxides become the preferred oxidation products. The e.s.r. spectrum of an ethylenebisgalvinoxyl biradical is described.

  一系列 4,4'-亚烷基双（2,6-二叔丁基苯酚 研究了一系列 4,4'-亚烷基双（2,6-二叔丁基苯酚）的氧化反应。 考察了一系列 4,4'-亚烷基双（2,6-二对丁基苯酚）的氧化过程。在 在单取代的化合物中，单苯氧基自由基的稳定性随着取代基大小的增加而增加。 随着取代基大小的增加，单苯氧基自由基的稳定性增加，而半乙酰氧基自由基的稳定性降低。β-偶联产物 只从亚乙基双酚中获得，这一结果与 e.s.r. 超频分裂常数相关联。随着单取代基或双取代基的增加，双螺过氧化物成为首选的 氧化产物。描述了乙烯-双丙烯酰氧基双环氧乙烷的 e.s.r. 光谱。 双环氧乙烷的 e.s.r. 光谱。
• Redox potentials, laccase oxidation, and antilarval activities of substituted phenols
  作者：Keshar Prasain、Thi D.T. Nguyen、Maureen J. Gorman、Lydia M. Barrigan、Zeyu Peng、Michael R. Kanost、Lateef U. Syed、Jun Li、Kun Yan Zhu、Duy H. Hua

  DOI：10.1016/j.bmc.2012.01.021

  日期：2012.3

  Laccases are copper-containing oxidases that are involved in sclerotization of the cuticle of mosquitoes and other insects. Oxidation of exogenous compounds by insect laccases may have the potential to produce reactive species toxic to insects. We investigated two classes of substituted phenolic compounds, halogenated di- and trihydroxybenzenes and substituted di-tert-butylphenols, on redox potential, oxidation by laccase and effects on mosquito larval growth. An inverse correlation between the oxidation potentials and laccase activity of halogenated hydroxybenzenes was found. Substituted di-tert-butylphenols however were found to impact mosquito larval growth and survival. In particular, 2,4-di-tert-butyl-6-(3-methyl-2-butenyl)phenol (15) caused greater than 98% mortality of Anopheles gambiae larvae in a concentration of 180 nM, whereas 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropanal oxime (13) and 6,8-di-tert-butyl-2,2-dimethyl-3,4-dihydro-2H-chromene (33) caused 93% and 92% mortalities in concentrations of 3.4 and 3.7 mu M, respectively. Larvae treated with di-tert-butylphenolic compounds died just before pupation. (C) 2012 Elsevier Ltd. All rights reserved.
• Oxygenation of 2,6-di-tert-butylphenols bearing an electron-withdrawing group in the 4-position
  作者：Akira Nishinaga、Tadashi Shimizu、Yasushi Toyoda、Teruo Matsuura、Ken Hirotsu

  DOI：10.1021/jo00133a009

  日期：1982.6
• 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.