N-decanoyl imidazole | 69205-88-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-decanoyl imidazole
• 英文别名: 1-Imidazol-1-yldecan-1-one
• CAS: 69205-88-5
• 化学式: C₁₃H₂₂N₂O
• 分子量: 222.33
• InChiKey: WNWIKUKDMAMESS-UHFFFAOYSA-N

物化性质

• 沸点：
  341.3±25.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  N-decanoyl imidazole 在 盐酸羟胺 作用下， 反应 0.75h， 以155 mg的产率得到n-decanohydroxamic acid
  参考文献：
  名称：

  一种环境可持续的机械化学合成异羟肟酸衍生物的途径

  摘要：

  提出了通过高能机械化学活化将羧酸简单，经济地转化为异羟肟酸衍生物的方法。该球磨方法论已应用于多种羧酸，大大改善了与此类分子相关的纯化问题，而这些问题仍然是经典方法学的主要瓶颈之一。

  DOI：

  10.1002/adsc.201600350
• 作为产物：
  描述：

  正癸酸 、 N,N'-羰基二咪唑 反应 0.08h， 生成 N-decanoyl imidazole
  参考文献：
  名称：

  一种环境可持续的机械化学合成异羟肟酸衍生物的途径

  摘要：

  提出了通过高能机械化学活化将羧酸简单，经济地转化为异羟肟酸衍生物的方法。该球磨方法论已应用于多种羧酸，大大改善了与此类分子相关的纯化问题，而这些问题仍然是经典方法学的主要瓶颈之一。

  DOI：

  10.1002/adsc.201600350

文献信息

• Selective Acylation of Nucleosides, Nucleotides, and Glycerol-3-phosphocholine in Water
  作者：Matthew Powner、Christian Fernández-García

  DOI：10.1055/s-0036-1588626

  日期：——

  2′,3′,5′-tri-O-acetyl-nucleosides in water has been developed. Furthermore, a long-chain selective glycerol-3-phosphocholine diacylation is elucidated. These reactions are environmentally benign, rapid, high yielding, and the products are readily purified. Importantly, this reaction may indicate a prebiotically plausible reaction pathway for the selective acylation of key metabolites to facilitate their

  2',3'-二-O-乙酰基-核苷酸-5'-磷酸、2',3'-二-O-乙酰-核苷酸-5'-三磷酸和2',3',5的方便选择性合成'-tri-O-乙酰基-核苷在水中得到了开发。此外，还阐明了长链选择性甘油-3-磷酸胆碱二酰化。这些反应对环境无害、快速、收率高，并且产物易于纯化。重要的是，该反应可能表明关键代谢物的选择性酰化以促进它们并入原代谢中的益生元似是而非的反应途径。
• Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling
  作者：Claudia Bonfio、Cécile Caumes、Colm D. Duffy、Bhavesh H. Patel、Claudia Percivalle、Maria Tsanakopoulou、John D. Sutherland

  DOI：10.1021/jacs.8b12331

  日期：2019.3.6

  Starting with a mixture of activated carboxylic acids of different lengths, iterative cycling of acylation and hydrolysis steps allowed for the selection of longer-chain acylglycerol-phosphates. Our results suggest that a selection pathway based on energy-dissipative cycling could have driven the selective synthesis of phospholipids on early Earth.

  生命起源研究的主要目的是寻找从益生元化学到新生生物学的合理转变序列。在这种情况下，了解早期地球上磷脂膜是如何以及何时出现的，对于阐明导致原始细胞出现的益生元途径至关重要。在这里，我们表明将 glycerol-2-phosphate 暴露于酰化剂会导致形成 acylglycerol-phosphates 库。发现中链酰基甘油磷酸酯自组装成囊泡，在各种条件下稳定，并能够保留单核苷酸和寡核苷酸。从不同长度的活化羧酸混合物开始，酰化和水解步骤的迭代循环允许选择更长链的酰基甘油-磷酸酯。
• 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。
• A facile preparation of highly functionalized cyclopropanes and their conversion to cyclopentanones and furans
  作者：Phil Ho Lee、Jong Soon Kim、Youn Chul Kim、Sunggak Kim

  DOI：10.1016/s0040-4039(00)60406-9

  日期：1993.11

  It was found that cyclopentanones and furans were prepared from 1-alkenyl-1-methoxycyclopropane derivatives derived from the conjugate addition of 1-methoxy-2-alkenylidenephosphoranes to activated olefins.

  发现环戊烷酮和呋喃是由1-烯基-1-甲氧基环丙烷衍生物制备的，所述衍生物是将1-甲氧基-2-烯基亚膦酰基膦酸酯共轭加成到活化烯烃上而得的。
• Synthesis of Deuterated and Protiated Triacylglycerides by Using 1,1’‐Carbonyldiimidazole Activated Fatty Acids
  作者：Kuno Schwärzer、Theresia Heiden‐Hecht、Yao Chen、Olaf Holderer、Henrich Frielinghaus、Peixun Li、Jürgen Allgaier

  DOI：10.1002/ejoc.202300632

  日期：2023.10.21

  Synthetic model triacylglyceride oils are important compounds for applications in pharmaceutical and food chemistry. Herein, a practical and highly efficient methodology for the synthesis of saturated and unsaturated triacylglycerides utilizing saturated and unsaturated fatty acids activated by 1,1’‐carbonyldiimidazole (CDI) has been developed and applied in the synthesis of deuterated medium chain triglyceride (MCT) oil for studies of plant‐based and diary food emulsions. The deuterium labelled compounds were used to gain new insight into the mechanism of the reaction, which was confirmed by density‐functional theory (DFT) calculations.

  摘要 合成模型三酰甘油是应用于医药和食品化学的重要化合物。本文开发了一种利用饱和和不饱和脂肪酸经 1,1'-羰基二咪唑（CDI）活化合成饱和和不饱和三酰甘油的实用高效方法，并将其应用于氘代中链甘油三酯（MCT）油的合成，用于植物基和乳化食品的研究。利用氘标记化合物对反应机理有了新的认识，密度函数理论（DFT）计算也证实了这一点。