2,4,6-tri-tert-butylacetophenone | 22744-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-tert-butylacetophenone
• 英文别名: 2,4,6-Tri-tert.-butylacetophenon；1-(2,4,6-Tritert-butylphenyl)ethanone
• CAS: 22744-29-2
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: PTPSXIRSIBHYRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  120.5-122.0 °C(Solv: methanol (67-56-1))
• 沸点：
  335.0±41.0 °C(Predicted)
• 密度：
  0.898±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-tert-butylacetophenone 在 正丁基锂 、 三甲基硅烷 、 sodium hydroxide 作用下， 以 乙醚 、 正己烷 、 水 、 正戊烷 为溶剂， 反应 0.17h， 生成 3-(2',4',6'-tri-tert-butylphenyl)-3-hydroxypropenoic acid
  参考文献：
  名称：

  Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes

  摘要：

  Hydrophobically shielded alkynes HC C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DC C-aryl furnished initially only the E stereoisomer of DHC=C(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-C C-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3 produced H2C=C(-SnMe3)-aryl with well resolved long range Sn-119 NMR coupling constants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.002
• 作为产物：
  描述：

  1-溴-2,4,6-三叔丁基苯 在 吡啶 、 copper(l) iodide 、 正丁基锂 、 氯化亚砜 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 3.0h， 生成 2,4,6-tri-tert-butylacetophenone
  参考文献：
  名称：

  Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes

  摘要：

  Hydrophobically shielded alkynes HC C-aryl, carrying 2,6-di- and 2,4,6-tri-tert-butylphenyl as the aryl group, can add aqueous HBr on heating in moist chloroform solutions to produce pure H2C=C(-Br)-aryl (isolated yields 96%, no hydrolysis). Employment of DC C-aryl furnished initially only the E stereoisomer of DHC=C(-Br)-aryl (stereospecific syn addition), which was slowly both dedeuteriated and partially transformed to the Z stereoisomer by HBr. The strongly retarded HBr addition to H3C-C C-aryl in moist chloroform produced again more E than Z product, whereas a thermodynamic E/Z ratio of 10:87 was found in moist acetic acid. Substitution of Br by LiSnMe3 produced H2C=C(-SnMe3)-aryl with well resolved long range Sn-119 NMR coupling constants. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.002

文献信息

• Mechanistic Studies of Adamantylacetophenones with Competing Reaction Pathways in Solution and in the Crystalline Solid State
  作者：Vince M. Hipwell、Miguel A. Garcia-Garibay

  DOI：10.1021/acs.joc.9b01720

  日期：2019.9.6

  engineer and observe competing Norrish type II reaction pathways in the crystalline state. It was shown that excited state competition for hydrogen abstraction between secondary adamantyl and benzylic hydrogens is affected not only by the relative bond dissociation energies but also by the molecular conformation in the crystal. The subsequent fate of the resulting biradical species is determined by competition

  晶体中的光化学反应是在分子迁移性受到严格限制的条件下发生的，因此即使在气相或溶液中可以观察到许多其他产物，通常也只能得到一种产物。在金刚烷基和邻位均具有γ-氢原子的一系列2-（1-金刚烷基）-邻烷基苯乙酮选择芳香族基团来确定是否可以设计和观察处于结晶状态的竞争性Norrish II型反应途径。结果表明，在仲金刚烷基氢和苄基氢之间的激发态竞争夺取氢不仅受到相对键解离能的影响，而且还受到晶体中分子构象的影响。通过自由基重组形成光产物与反向氢原子转移以再生起始酮之间的竞争来确定所得双自由基物质的后续命运。报告了晶体学信息，溶液和固态中的光产物分布，以及多种机理实验的结果，包括乙腈中的瞬态吸收光谱法和悬浮在水中的纳米晶体。
• METAL COMPLEXES
  申请人：Stoessel Philipp

  公开号：US20130082209A1

  公开（公告）日：2013-04-04

  The present invention relates to metal complexes and to elec tronic devices, in particular organic electroluminescent devices, com-pris ing these metal complexes. M(L)n(L′)m (formula 1), where the compound of the gene ral formula (1) contains a moiety M(L)n of the formula (2).

  本发明涉及金属配合物和电子设备，特别是包含这些金属配合物的有机电致发光器件。其中，通式（1）的化合物包含式（2）的M(L)n基团。
• Lauer,D.; Staab,H.A., Chemische Berichte, 1969, vol. 102, p. 1631 - 1640
  作者：Lauer,D.、Staab,H.A.

  DOI：——

  日期：——
• Hartke, Klaus; Gerber, Hans-Dieter; Roesrath, Ulrich, Liebigs Annalen der Chemie, 1991, # 9, p. 903 - 916
  作者：Hartke, Klaus、Gerber, Hans-Dieter、Roesrath, Ulrich

  DOI：——

  日期：——
• Synthesis and photochemistry of 2,4,6-tri-tert-butylacetophenone
  作者：Steven R. Ditto、Roger J. Card、Paul D. Davis、Douglas C. Neckers

  DOI：10.1021/jo01319a066

  日期：1979.3