1-(1H-咪唑-1-基)-3-甲基丁烷-1-酮 | 10364-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(1H-咪唑-1-基)-3-甲基丁烷-1-酮
• 英文名称: N-isovalerylimidazole
• 英文别名: 1-Imidazol-1-yl-3-methylbutan-1-one；1-imidazol-1-yl-3-methylbutan-1-one
• CAS: 10364-92-8
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: PUARJWGNKXFFOB-UHFFFAOYSA-N

物化性质

• 沸点：
  255.2±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1H-咪唑-1-基)-3-甲基丁烷-1-酮 在 正丁基锂 、 diethylzinc 、 二异丙胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Resorcinol Amide Hsp90 Inhibitor AT13387

  摘要：

  The synthesis of C-5-substituted resorcinol amide AT13387, a known Hsp90 inhibitor currently in clinical trials, is reported without the use of phenolic protection in an overall yield of 13.4%. Biomimetic aromatization and Suzuki-Miyaura cross coupling approach were employed to synthesize the resorcinol and iso-indoline units, respectively, which were efficiently coupled using Grignard-mediated amidation.

  DOI：

  10.1021/jo302406w
• 作为产物：
  描述：

  异戊酸 以98的产率得到1-(1H-咪唑-1-基)-3-甲基丁烷-1-酮
  参考文献：
  名称：

  J. Org. Chem. 2012, 77, 11296-11301

  摘要：

  DOI：

文献信息

• Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters
  作者：Yongseok Park、Xiang Fei、Yue Yuan、Sanha Lee、Joonseong Hur、Sung Jean Park、Jae-Kyung Jung、Seung-Yong Seo

  DOI：10.1039/c7ra05287a

  日期：——

  Two different ways to carry out the chemoselective acylation of 2-amino-8-quinolinol with unique features to generate C2-amides or C8-esters were developed. The coupling reaction with a variety of carboxylic acids using EDCI and DMAP provided C8-ester derivatives, whereas N-heteroaromatic acids were not introduced on the C8-hydroxy group, but rather on the C2-amino group under the same conditions.

  开发了两种不同的方法来进行具有独特特征的2-氨基-8-喹啉醇的化学选择性酰化反应，以生成C2-酰胺或C8-酯。使用EDCI和DMAP与多种羧酸的偶联反应提供了C8-酯衍生物，而在相同条件下，N-杂芳族酸没有引入C8-羟基上，而是引入了C2-氨基上。为了选择性地获得C 2-酰胺，将来自2-氨基-8-喹啉醇的阴离子亲核试剂用反应性较小的酰基咪唑啉化物或酯处理。
• Biosynthesis of Branched-chain Fatty Acid in<i>Bacilli</i>: FabD (malonyl-CoA:ACP transacylase) Is Not Essential for<i>In Vitro</i>Biosynthesis of Branched-chain Fatty Acids
  作者：Hirosuke OKU、Naoya FUTAMORI、Kenichi MASUDA、Yumiko SHIMABUKURO、Tomoyo OMINE、Hironori IWASAKI

  DOI：10.1271/bbb.67.2106

  日期：2003.1

  It was found that the partially purified β-ketoacyl-ACP synthase of Bacillus insolitus did not require the addition of FabD (malonyl-CoA:ACP transacylase, MAT) for the activity assay. This study therefore examined the necessity of FabD protein for in vitro branched-chain fatty acid (BCFA) biosynthesis by crude fatty acid synthetases (FAS) of Bacilli. To discover the involvement of FabD in the BCFA biosynthesis, the protein was removed from the crude FAS by immunoprecipitation. The His-tag fusion protein FabD of Bacillus subtilis was expressed in Escherichia coli and used for the preparation of antibody. The rabbit antibody raised against the expressed fusion protein specifically recognized the FabD in the crude FAS of B. subtilis. Evaluation of the efficacy of the immunoprecipitation showed that a trace of FabD protein was present in the antibody-treated crude FAS. However, this complete removal of FabD from the crude FAS did not abolish its BCFA biosynthesis, but only reduced the level to 50-60% of the control level for acyl-CoA primer and to 80% for α-keto-β-methylvalerate primer. Furthermore, the FabD concentration did not necessarily correlate with the MAT specific activity in the enzyme fractions, suggesting the presence of another enzyme source of MAT activity. This study, therefore, suggests that FabD is not the sole enzyme source of MAT for in vitro BCFA biosynthesis, and implies the existence of a functional connection between fatty acid biosynthesis and another metabolic pathway.

  研究发现，不完全纯化的无枝菌酸菌β-酮脂酰ACP合酶（Bacillus insolitus）在活性测定时不需要添加FabD（丙二酸单酰-CoA:ACP转酰酶，MAT）。因此，本研究探讨了杆状菌粗脂肪酸合成酶（FAS）体外支链脂肪酸（BCFA）生物合成中FabD蛋白的必要性。为了探索FabD在BCFA生物合成中的作用，通过免疫沉淀法从粗FAS中去除该蛋白。将枯草芽孢杆菌的His标签融合蛋白FabD在大肠杆菌中表达，并用其制备抗体。针对表达的融合蛋白免疫兔子得到的抗体能特异性地识别枯草芽孢杆菌粗FAS中的FabD。免疫沉淀法效力评估显示，经抗体处理的粗FAS中仅残留极少量的FabD蛋白。然而，从粗FAS中完全去除FabD并未使其BCFA生物合成失活，仅使其活性降低，对于酰基-CoA引物降至对照组的50-60%，对于α-酮基-β-甲基戊酸引物降至80%。此外，FabD浓度与酶组分中MAT的特异性活性并不一定相关，表明存在另一种MAT活性的酶源。因此，本研究认为，FabD不是体外BCFA生物合成中MAT唯一的酶源，并暗示脂肪酸生物合成与其他代谢途径之间存在功能联系。
• Supramolecular Catalysis of Acyl Transfer within Zinc Porphyrin-Based Metal–Organic Cages
  作者：LiLi Li、Linlin Yang、Xuezhao Li、Jing Wang、Xin Liu、Cheng He

  DOI：10.1021/acs.inorgchem.1c00745

  日期：2021.6.21

  To illustrate the supramolecular catalysis process in molecular containers, two porphyrinatozinc(II)-faced cubic cages with different sizes were synthesized and used to catalyze acyl-transfer reactions between N-acetylimidazole (NAI) and various pyridylcarbinol (PC) regioisomers (2-PC, 3-PC, and 4-PC). A systemic investigation of the supramolecular catalysis occurring within these two hosts was performed

  为了说明分子容器中的超分子催化过程，合成了两种不同尺寸的卟啉锌（II）面立方笼，并用于催化 N-乙酰咪唑（NAI）与各种吡啶基甲醇（PC）区域异构体（2-PC）之间的酰基转移反应、3-PC 和 4-PC）。结合主客体结合研究和密度泛函理论计算，对这两种主体内发生的超分子催化进行了系统研究。相比于块状溶剂中进行反应，结果该2-PC的反应被认为是与高速率增强高效（ķ猫/ ķ uncat = 283为Zn的1和442的Zn-2)，以及与各种邻位取代的 2-PC 底物和 NAI 衍生物反应的不同效率应归因于具有预浓缩和预取向底物的笼子。同一个笼子对不同的 PC 区域异构体表现出不同的催化活性，这主要是由于笼子的各个反应物和产物之间的结合亲和力不同。此外，还进行了对照实验以了解不同反应物浓度和产物抑制的影响。结果都表明，除了内部微环境引起的限制效应外，底物转移，包括反应物的包封和产物的释放，应该被认
• N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins
  作者：Anna Lee、Karl A. Scheidt

  DOI：10.1039/c4cc09590a

  日期：——

  A highly efficient asymmetric formal [4+2] annulation for the synthesis of dihydrocoumarins has been developed via an in situ activated NHC catalysis. Both electrophilic and nucleophilic species are generated in situ simultaneously whereby acyl imidazoles facilitated rapid formation of an NHC-enolate intermediate to afford the [4+2] dihydrocoumarin adducts.

  通过原位活化的NHC催化，已经开发出了一种高效的不对称形式[4 + 2]正式环用于合成二氢香豆素。亲电物质和亲核物质同时在原位产生，因此酰基咪唑促进了NHC-烯醇酸酯中间体的快速形成，从而提供了[4 + 2]二氢香豆素加合物。
• Synthesis of 6-Substituted-4-Hydroxy-2-pyridinones via Intramolecular Ketene Trapping of Functionalized Enamine-Dioxinones
  作者：Bhavesh H. Patel、Andrew M. Mason、Anthony G. M. Barrett

  DOI：10.1021/ol202028t

  日期：2011.10.7

  The synthesis of various 6-substituted-4-hydroxy-2-pyridinones is reported. The functionalized keto-dioxinones were constructed via a diethylzinc mediated crossed Claisen condensation reaction and subsequent enamine formation, thermolysis, and cyclization–aromatization providing the pyridinone unit.

  报道了各种6-取代的-4-羟基-2-吡啶酮的合成。通过二乙基锌介导的交叉克莱森缩合反应和随后的烯胺形成，热解和环化芳香化反应构建了功能化的酮二恶酮，从而提供了吡啶酮单元。