1-(2,4,6-trimethylphenyl)-1-buten-3-one | 53389-56-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(2,4,6-trimethylphenyl)-1-buten-3-one
• 英文别名: 4-Mesityl-3-buten-2-one；4-(2,4,6-trimethylphenyl)but-3-en-2-one
• CAS: 53389-56-3
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: LWXBQPWVAVMPDK-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  304.6±11.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  1-(2,4,6-trimethylphenyl)-1-buten-3-one 在 盐酸 、 sodium methylate 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 9.0h， 生成 3-hydroxy-5-(2,4,6-trimethylphenyl)-2-propionyl-cyclohex-2-en-1-one
  参考文献：
  名称：

  三甲苯草酮的制备方法

  摘要：

  本发明公开了一种制备三甲苯草酮的方法，包括：利用2，4，6‑三甲基苯甲醛和丙酮，制备第一中间体；利用第一中间体、丙二酸二乙酯和丙酰氯，制备第二中间体；利用第二中间体和乙氧胺，制备三甲苯草酮；在所述制备第二中间体的过程中，缩合、重排反应同时进行；在所述制备第一中间体之后、所述制备三甲苯草酮之前，不进行分离或纯化处理。本发明通过缩合、重排反应同时进行，以及在反应过程不进行分离或纯化过程制备三甲苯草酮，省去了现有制备方法中多次分离、纯化、转移、投料等步骤，省时、省力，且减少了试剂的消耗，节约了大量的成本，解决了现有技术中三甲苯草酮的制备方法步骤复杂、产品收率较低、酯化反应过程分层乳化严重的问题。

  公开号：

  CN113024411B
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 、 1-三苯基膦-2-丙酮 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1-(2,4,6-trimethylphenyl)-1-buten-3-one
  参考文献：
  名称：

  Cyclohexane 1,3-diones and their inhibition of mutant SOD1-dependent protein aggregation and toxicity in PC12 cells

  摘要：

  Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons. Currently, there is only one FDA-approved treatment for ALS (riluzole), and that drug only extends life, on average, by 2-3 months. Mutations in Cu/Zn superoxide dismutase (SOD1) are found in familial forms of the disease and have played an important role in the study of ALS pathophysiology. On the basis of their activity in a PC12-G93A-YFP high-throughput screening assay, several bioactive compounds have been identified and classified as cyclohexane-1,3-dione (CHD) derivatives. A concise and efficient synthetic route has been developed to provide diverse CHD analogs. The structural modification of the CHD scaffold led to the discovery of a more potent analog (26) with an EC(50) of 700 nM having good pharmacokinetic properties, such as high solubility, low human and mouse metabolic potential, and relatively good plasma stability. It was also found to efficiently penetrate the blood-brain barrier. However, compound 26 did not exhibit any significant life span extension in the ALS mouse model. It was found that, although 26 was active in PC12 cells, it had poor activity in other cell types, including primary cortical neurons, indicating that it can penetrate into the brain, but is not active in neuronal cells, potentially due to poor selective cell penetration. Further structural modification of the CHD scaffold was aimed at improving global cell activity as well as maintaining potency. Two new analogs (71 and 73) were synthesized, which had significantly enhanced cortical neuronal cell permeability, as well as similar potency to that of 26 in the PC12-G93A assay. These CHD analogs are being investigated further as novel therapeutic candidates for ALS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.039

文献信息

• Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites
  作者：R. B. Nasir Baig、Rajender S. Varma

  DOI：10.1039/c2gc36455g

  日期：——

  Magnetic nano-catalysts have been prepared using simple modification of iron ferrites. The nm size range of these particles facilitates the catalysis process, as an increased surface area is available for the reaction; the easy separation of the catalysts by an external magnet and their recovery and reuse are additional beneficial attributes. Glutathione bearing nano-ferrites have been used as organocatalysts for the Paal–Knorr reaction and homocoupling of boronic acids. Nanoferrites, post-synthetically modified by ligands, were used to immobilize nanometals (Cu, Pd, Ru, etc.) which enabled the development of efficient, sustainable and green procedures for azide–alkynes-cycloaddition (AAC) reactions, C–S coupling, O-allylation of phenol, Heck-type reactions and hydration of nitriles.

  通过简单修饰铁氧体，已制备出磁性纳米催化剂。这些粒子处于纳米尺寸范围，有助于催化过程，因为反应可利用增加的表面积；外部磁铁易于分离催化剂，并可回收和重复使用，这些是额外的有益特性。负载谷胱甘肽的纳米铁氧体已用作有机催化剂，用于Paal-Knorr反应和硼酸的均偶联。通过配体后合成改性的纳米铁氧体，用于固定纳米金属（铜、钯、钌等），从而实现了高效、可持续和绿色的叠氮-炔烃环加成（AAC）反应、碳-硫偶联、酚的烯丙基化、 Heck型反应和腈的水合反应的方法发展。
• Stereodivergent Pd/Cu Catalysis for the Dynamic Kinetic Asymmetric Transformation of Racemic Unsymmetrical 1,3-Disubstituted Allyl Acetates
  作者：Rui He、Xiaohong Huo、Ling Zhao、Feijun Wang、Liyin Jiang、Jian Liao、Wanbin Zhang

  DOI：10.1021/jacs.0c02150

  日期：2020.5.6

  stereodivergent Pd/Cu catalyst system has been developed for the unprecedented dynamic kinetic asymmetric transformation (DyKAT) of racemic unsymmetrical 1,3-disubstituted allylic acetates with prochiral aldimine esters. A series of α,α-disubstituted α-amino acids bearing vicinal stereocenters were easily prepared with excellent enantioselectivities (up to >99% ee) and diastereoselectivities (up to >20:1 dr). By

  已经开发了一种立体发散的 Pd/Cu 催化剂体系，用于外消旋不对称 1,3-二取代烯丙基乙酸酯与前手性醛亚胺酯的前所未有的动态动力学不对称转化 (DyKAT)。一系列带有邻位立体中心的 α,α-二取代 α-氨基酸很容易制备，具有优异的对映选择性（高达 >99% ee）和非对映选择性（高达 >20:1 dr）。通过简单地改变两种手性金属催化剂的构型，可以很容易地获得产物的所有四种立体异构体。此外，我们的工作突出了由两种常见的双齿手性配体组成的协同 Pd/Cu 催化的力量，用于立体发散​​合成。
• Enantioselective Aminocatalytic [2 + 2] Cycloaddition through Visible Light Excitation
  作者：Thomas Rigotti、Rubén Mas-Ballesté、José Alemán

  DOI：10.1021/acscatal.0c01413

  日期：2020.5.1

  to obtain enantioenriched cyclobutanes through [2 + 2] photocycloaddition under visible light irradiation is presented. This metal-free process does not require the use of any external photocatalyst, as it is catalyzed by a simple diamine which, upon condensation with an enone substrate, forms an iminium ion intermediate that absorbs in the visible light region. The direct excitation of such an intermediate

  提出了在可见光下通过[2 + 2]光环加成反应获得对映体富集的环丁烷的不对称氨基催化活化策略。这种无金属的方法不需要使用任何外部光催化剂，因为它是由简单的二胺催化的，该二胺与烯酮底物缩合后，形成在可见光区域吸收的亚胺离子中间体。这种中间体的直接激发导致电荷转移（CT）激发态，该态以良好的对映异构体和非对映异构体比率和高收率解锁立体控制的分子间光环加成反应。最后，进行了DFT计算和实验以支持电荷转移行为和机理建议。
• Herbicidal 5-(acylphenyl)cyclohexane-1,3-dione derivatives
  申请人：ICI Australia Limited

  公开号：US04652303A1

  公开（公告）日：1987-03-24

  The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of: the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--; the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation; the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.7 form a heterocyclic ring; X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives thereof; R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation; R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl; R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; R.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl; m is selected from integers 1 and 2; n is selected from the integers 1 to 4; and m+n is selected from the integers 3 to 5. The compounds of the invention show herbicidal properties and plant growth regulating properties and in further embodiments the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of the compounds of formula I, compositions containing as active ingredient a compound of formula I, and herbicidal and plant growth regulating processes utilizing compounds of formula I.

  本发明涉及公式I的新化合物：##STR1##其中：W选择自R.sup.5 --CO--和R.sup.5 --CS--组，其中：R.sup.5选择自烯丙基，炔基，苯甲基，苯基，取代基烷基，取代基烯丙基，取代基炔基，取代基苯甲基，取代基苯基和羟缩醛，半缩醛，肟，亚胺和Schiff碱衍生物的R.sup.5 --CO--组；Y--CO--和Y--CS--组，其中Y选择自羟基，巯基，烷基硫和MO--和MS--组，其中M是有机或无机阳离子；R.sup.6 R.sup.7 NCO--和R.sup.6 R.sup.7 NCS--组，其中R.sup.6和R.sup.7独立地选择自氢，烷基，取代基烷基，脂肪酰，羧基，烷氧羰基，烷基磺酰，苯甲酰，苯磺酰，取代基苯甲酰，取代基苯磺酰，或R.sup.6和R.sup.7形成杂环；X选择自卤素，硝基，氰基，烷基，取代基烷基，羟基，烷氧基，取代基烷氧基，烯丙基，烯丙氧基，炔基，取代基炔基，酰氧基，烷氧羰基，烷基硫，烷基亚磺酰，烷基磺酰，磺酰胺，取代基磺酰胺，脂肪酰氧基，苯甲氧基，取代基苯甲氧基，氨基，取代基氨基，以及羰基和脂肪酰基和其羟缩醛，半缩醛，肟，亚胺和Schiff碱衍生物；R.sup.1选择自氢，烷基，烯丙基，炔基，取代基烷基，烷基磺酰，芳基磺酰，酰基和无机或有机阳离子；R.sup.2选择自烷基，取代基烷基，烯丙基，卤代烯丙基，炔基和卤代炔基；R.sup.3选择自烷基，氟代烷基，烯丙基，炔基和苯基；R.sup.4选择自氢，卤素，烷基，氰基和烷氧羰基；m选择自1和2的整数；n选择自1到4的整数；m+n选择自3到5的整数。本发明化合物具有除草和植物生长调节性质，在进一步实施中，本发明提供了制备公式I化合物的过程，制备公式I化合物的中间体，含有公式I化合物作为活性成分的组合物，以及利用公式I化合物的除草和植物生长调节过程。
• Cyclohexenone derivatives and their herbicidal use.
  申请人：ICI Australia Limited

  公开号：US04666510A1

  公开（公告）日：1987-05-19

  The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof; R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation; R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl; R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; m is an integer chosen from 3 to 5. The compounds of the invention show herbicidal properties and plant growth regulating properties and in further embodiments the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of the compounds of formula I, compositions containing as active ingredient a compound of formula I, and herbicidal and plant growth regulating processes utilizing compounds of formula I.

  本发明涉及公式I的新化合物：##STR1##其中：X选择自卤素、硝基、氰基、烷基、取代烷基、羟基、烷氧基、取代烷氧基、烯基、炔基、烯氧基、炔氧基、酰氧基、烷氧羰基、烷硫基、烷基亚砜基、烷基磺酰基、磺酰胺基、取代磺酰胺基、氨基、取代氨基以及酰肟、亚胺和席夫碱衍生物；R.sup.1选择自氢、烷基、烯基、炔基、取代烷基、烷基磺酰基、芳基磺酰基、酰基和无机或有机阳离子；R.sup.2选择自烷基、取代烷基、烯基、卤代烯基、炔基和卤代炔基；R.sup.3选择自烷基、氟烷基、烯基、炔基和苯基；m是从3到5的整数。本发明的化合物具有除草和植物生长调节性能，另外，本发明提供了公式I化合物的制备方法、制备公式I化合物的中间体、含有公式I化合物作为活性成分的组合物以及利用公式I化合物进行除草和植物生长调节的方法。