4-t-butylbenzylideneacetone | 65178-75-8

• 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: 4-t-butylbenzylideneacetone
• 英文别名: 4-(4-tert-butylphenyl)but-3-en-2-one
• CAS: 65178-75-8
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: SSWAKZIHXNIMGR-UHFFFAOYSA-N

物化性质

• 沸点：
  305.3±11.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-t-butylbenzylideneacetone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 4-(4-tert-butylphenyl)butan-2-one
  参考文献：
  名称：

  （E）-3,4-二羟基苯乙烯基对取代苯乙酮衍生物的合成及神经保护作用评价抗炎性和氧化性损伤

  摘要：

  合成了（E）-3,4-二羟基苯乙烯基对位取代的苯乙基酮及其3,4-二乙酰化衍生物，并检查了它们的神经保护活性，以进一步研究对位取代基对芳环的影响。结果表明，p-取代基的空间位阻效应影响了对炎症和氧化损伤的神经保护活性。与较小的组相比，引入较大的组更有利于改善神经保护活性。化合物（4 - 5H，4 - 5I和4 - 5E）具有p取代的三氟甲基，异丙基和在所有目标化合物中，叔丁基均表现出最佳效果。

  DOI：

  10.1007/s00044-016-1601-3
• 作为产物：
  描述：

  对叔丁基苯甲醛 、 1-三苯基膦-2-丙酮 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 4-t-butylbenzylideneacetone
  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

• Selective Cross-Dehydrogenative C(sp³)–H Arylation with Arenes
  作者：Hong-Yan Hao、Yang-Jie Mao、Zhen-Yuan Xu、Shao-Jie Lou、Dan-Qian Xu

  DOI：10.1021/acs.orglett.0c00588

  日期：2020.3.20

  Selective C(sp3)-C(sp2) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp3)-H and C(sp2)-H bonds represents an attractive alternative toward new C(sp3)-C(sp2) bonds. Herein, we establish a selective inter- and intramolecular C(sp3)-H arylation of alcohols with nondirected arenes

  选择性的C（sp3）-C（sp2）键结构是化学合成中的主要关注点。尽管经典的交叉偶联反应成功，但惰性C（sp3）-H和C（sp2）-H键之间的交叉脱氢偶联代表了对新C（sp3）-C（sp2）键的有吸引力的替代选择。在本文中，我们建立了醇与非定向芳烃的选择性分子间和分子内C（sp3）-H芳基化反应，从而提供了访问广泛的β-芳基化醇的一般途径，包括四氢萘-2-醇和苯并吡喃-3-具有高至优异的化学和区域选择性的醇。
• Enantioselective Organocatalytic Conjugate Addition of Alkenes to α,β-Enones
  作者：Lingyun Cui、Long Zhang、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/ejoc.201402353

  日期：2014.6

  We report the first example of the enantioselective conjugate addition of alkenes (aromatic enamines) to enones catalyzed by chiral primary amines. The reactions encompass a plethora of α,β-enones including difficult α-substituted vinyl ketones to give vinylation adducts in high yields with good enantioselectivity. The methodology is of synthetic potential in accessing chiral functional materials.

  我们报告了烯烃（芳香族烯胺）与手性伯胺催化的烯酮对映选择性共轭加成的第一个例子。该反应包括大量的 α,β-烯酮，包括难以生成的 α-取代乙烯基酮，以高产率和良好的对映选择性得到乙烯基化加合物。该方法在获得手性功能材料方面具有合成潜力。
• One-Pot Photomediated Giese Reaction/Friedel–Crafts Hydroxyalkylation/Oxidative Aromatization To Access Naphthalene Derivatives from Toluenes and Enones
  作者：Haiwang Liu、Lishuang Ma、Rong Zhou、Xuebo Chen、Weihai Fang、Jie Wu

  DOI：10.1021/acscatal.8b00481

  日期：2018.7.6

  γ-aryl ketones and naphthalenes, were conveniently synthesized from readily available toluenes and enones through the synergistic combination of photoredox and Lewis acid catalysis. The direct synthesis of γ-aryl ketones represents a rare example of Giese reactions between benzylic C(sp3)–H and enones that avoids the use of prefunctionalized metallic nucleophiles. Naphthalene derivatives were accessed

  通过光氧化还原和路易斯酸催化的协同作用，可以方便地从易得的甲苯和烯酮中合成增值化学品γ-芳基酮和萘。γ-芳基酮的直接合成代表了苄基C（sp 3）–H与烯酮之间Giese反应的罕见例子，避免了使用预先官能化的金属亲核试剂。萘衍生物可通过一锅Giese反应/ Friedel-Crafts羟烷基化/氧化芳构化顺序转化获得。
• Synthesis and biological activity of novel tiliroside derivants
  作者：Nan Qin、Chun-Bao Li、Mei-Na Jin、Li-Huan Shi、Hong-Quan Duan、Wen-Yan Niu

  DOI：10.1016/j.ejmech.2011.07.059

  日期：2011.10

  A series of new tiliroside derivatives were synthesized and characterized by analytical H-1 NMR, C-13 NMR and mass spectrometry. All of the compounds were evaluated for anti-diabetic properties in vitro using HepG2 cells. Compounds 3c, 3d, and 3i-l caused significant enhancements in glucose consumption by insulin-resistant HepG2 cells compared with control cells and cells that were exposed to metformin (an anti-diabetic drug). Moreover, compound 3l significantly activated adenosine 5'-monophosphate-activated protein kinase activity and reduced acetyl-CoA carboxylase activity. Thus, the tiliroside derivative 3l offers potential to be developed as a new approach for treating type II diabetes. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Direct construction of 3′,4′-dihydrospiro[pyrrol-3,2′-oxindoles] through a cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals
  作者：Dao-Cai Wang、Hang Song、Chun-Yun Xu、Hui Dong、Jie Liu

  DOI：10.1016/j.cclet.2015.04.014

  日期：2015.8

  A simple and efficient cascade Michael/cyclization reaction of 3-aminoindolin-2-ones with enones/enals was identified for the synthesis of potentially biologically active 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles], using DBU as an efficient catalyst and ethylene glycol as an environmentally benign solvent. More diverse 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] analog libraries were prepared in good yields (up to 97%). The structure of 3',4'-dihydrospiro[pyrrol-3,2'-oxindoles] was confirmed by mass spectrometry analysis, NMR analysis and single crystal X-ray diffraction. The main advantages of this method include the availability of starting materials, simple experimental operation, short reaction time, as well as high yields observed. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.