2,4,6-trimethylbenzhydrol

• 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: 2,4,6-trimethylbenzhydrol
• 英文别名: mesityl(phenyl)methanol；Benzenemethanol, 2,4,6-trimethyl-alpha-phenyl-；phenyl-(2,4,6-trimethylphenyl)methanol
• 化学式: C₁₆H₁₈O
• mdl: MFCD06654252
• 分子量: 226.318
• InChiKey: WEJXJLHQHYCHDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4,6-trimethylbenzhydrol 生成 (+-)-benzoic acid-(2,4,6-trimethyl-benzhydryl ester)
  参考文献：
  名称：

  Davies et al., Journal of the Chemical Society, 1954, p. 3474,3478

  摘要：

  DOI：
• 作为产物：
  描述：

  3-Bromophenyl mesityl ketone 在 LDPA 作用下， 以 四氢呋喃 为溶剂， 反应 80.0h， 生成 2,4,6-trimethylbenzhydrol
  参考文献：
  名称：

  The use of chemical probes to differentiate between polar and SET-hydrogen atom abstraction pathways involved in the reduction reaction promoted by an 8-Al-4 anion

  摘要：

  The mechanism for the reduction of aromatic ketones and alkyl halides with lithium tetrakis(N-dihydropyridyl)aluminate was found to proceed competitively by hydride reduction and by single electron transfer (SET)-hydrogen atom abstraction processes. A series of ketyl fragmentation probes were used to differentiate the two pathways. A SET process is the dominant pathway when the ketones involved are sterically hindered or when strong electron acceptors are used as the substrates. The observation that EPR-active intermediates can be detected, or that small amounts of radical derived products are formed, demonstrates only that a SET pathway is available but cannot be used to establish the mechanism of the major product-forming reactions.

  DOI：

  10.1021/jo00074a014

文献信息

• Rhodium quinonoid catalysts
  申请人：Sweigart A. Dwight

  公开号：US20070117981A1

  公开（公告）日：2007-05-24

  In accordance with one aspect of the invention a rhodium quinonoid catalyst is disclosed.

  根据发明的某一方面，公开了一种铑醌类催化剂。
• An Efficient Ga(OTf)₃/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols
  作者：Masahiro Sai

  DOI：10.1002/adsc.201801135

  日期：2018.11.16

  first gallium‐catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst‐assisted hydride transfer of the in situ‐generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom‐economic and environmentally friendly approach to the synthesis of di‐ and triarylmethanes, which are important

  这项研究旨在报告使用异丙醇作为还原剂的镓催化的首次直接还原苄醇。反应通过原位生成的苄基异丙醚的镓催化剂辅助氢化物转移而进行。该方法仅产生副产物水和丙酮，因此为二芳基甲烷和三芳基甲烷的合成提供了一种原子经济且环保的方法，而二芳基甲烷和三芳基甲烷是各种生物活性化合物和功能材料中的重要子结构。
• AlCl₃ catalyzed coupling of N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon–nitrogen bond cleavage
  作者：Chen Hu、Gang Hong、Xiaofei Qian、Kwang Rim Kim、Xiaoyan Zhu、Limin Wang

  DOI：10.1039/c7ob01025g

  日期：——

  A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of the AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently

  报道了一种新的N-苄基磺酰胺与2-取代的氰基乙酸酯的交叉偶联反应，用于合成2-取代的苄基苯。在AlCl3的存在下，各种各样的N-苄基磺酰胺与2-取代的氰基乙酸酯平稳反应，以中等至极好的收率提供结构多样的苄基苯。转换可以有效地扩大到克级。该方法的实用性在具有高抗炎活性的相关生物活性剂的合成中得到进一步证明。
• <i>In situ</i>preparation of rhodium/<i>n</i>-heterocyclic carbene complexes and use for addition of arylboronic acids to aldehydes
  作者：Rafet Kilinçarslan、Engin Çetinkaya、Bekir Çetinkaya、Murat Yiǧit、İsmail Özdemir

  DOI：10.1002/jhet.5570440111

  日期：2007.1

  The in situ prepared three component system [RhCl(COD)]2/imidazolidinium salts (2, 4) and KOBut catalyses the addition of phenylboronic acid to sterically hindered aldehydes affording the corresponding arylated secondary alcohols in good yields. Four novel 1,3-dialkylimidazolidinium (2-4) salts as NHC precursors were synthesized from N,N′-dialkylethylenediamine.

  在原位制备的三个组分体系[的RhCl（COD）] 2 /咪唑烷鎓盐（2,4）和甲部吨催化加成苯基硼酸于空间位阻的醛，得到良好的收率相应芳基化的仲醇。从N，N'-二烷基乙二胺合成了4种新颖的1,3-二烷基咪唑啉鎓盐（2-4）作为NHC前体。
• Visible light photoredox-catalyzed deoxygenation of alcohols
  作者：Daniel Rackl、Viktor Kais、Peter Kreitmeier、Oliver Reiser

  DOI：10.3762/bjoc.10.223

  日期：——

  Carbon–oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon–oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and irradiation with blue light in the presence of [Ir(ppy)₂(dtb-bpy)](PF₆) as visible light photocatalyst and Hünig’s base as sacrificial electron donor in an acetonitrile/water mixture generally gave good to excellent yields of the desired defunctionalized compounds. Functional group tolerance is high but the protocol developed is limited to benzylic, α-carbonyl, and α-cyanoalcohols; with other alcohols a slow partial C–F bond reduction in the 3,5-bis(trifluoromethyl)benzoate moiety occurs.

  碳-氧单键在天然产物中普遍存在，而用于其还原脱官能团化的有效方法却很少见。在这项工作中，开发了一种对醇的碳-氧单键进行环境友好的激活，以实现在可见光光催化下的还原键裂解的方法。醇被激活为3,5-双(三氟甲基)取代苯甲酸酯，通过在蓝光照射下，在存在[Ir(ppy)₂(dtb-bpy)](PF₆)作为可见光光催化剂和Hünig's碱作为牺牲电子供体的乙腈/水混合物中，通常可以获得所需的脱官能化化合物的良好至优异产率。对官能团的耐受性很高，但所开发的方法仅限于苄基、α-羰基和α-氰基醇；对于其他醇，3,5-双(三氟甲基)苯甲酸酯中的部分C-F键还原会发生缓慢。