N-laurylimidazole | 3867-67-2

• 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-laurylimidazole
• 英文别名: Lauroyl-imidazol；1-Lauoryl-imidazol；Laurinsaeure-imidazolid；N-Lauroyl-imidazol；1-dodecanoyl-1H-imidazole；1-(1H-Imidazol-1-yl)dodecan-1-one；1-imidazol-1-yldodecan-1-one
• CAS: 3867-67-2
• 化学式: C₁₅H₂₆N₂O
• 分子量: 250.384
• InChiKey: ZXVWLELAQZOEQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  18.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  N-laurylimidazole 在 (S)-RuBINAP 氢气 作用下， 以 盐酸 、 甲醇 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 87.0h， 生成 S-(3)-羟基肉豆蔻酸甲酯
  参考文献：
  名称：

  Enantioselective Synthesis of α-Amino Acids from N-Tosyloxy β-Lactams Derived from β-Keto Esters

  摘要：

  A novel synthetic sequence has been developed to convert simple beta-keto esters into enantiomerically enriched alpha-amino acids. The key features of this sequence include the addition of azide to the C3 position of beta-keto ester derived N-tosyloxy-beta-lactams through a concomitant nucleophilic addition/ N-O bond reduction reaction, a mild CsF-induced N1 benzylation of a-azido monocyclic beta-lactams, the preparation of alpha-keto-beta-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-beta-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-beta-lactams is reported.

  DOI：

  10.1021/jo0162437
• 作为产物：
  描述：

  咪唑 、 月桂酰氯 以 氯仿 为溶剂， 反应 12.0h， 以90%的产率得到N-laurylimidazole
  参考文献：
  名称：

  胶束对N-酰基咪唑酸水解的影响

  摘要：

  在阴离子[十二烷基硫酸钠（NaLS）]和阳离子[十六烷基三甲基溴化铵（CTABr）]表面活性剂的存在下，已研究了各种N-酰基咪唑的酸催化水解。对于N-月桂酰基衍生物的水解，CTABr在pH升高的情况下会导致速率降低，该范围内观察到的速率常数在水中稳定下来，而NaLS不会影响相同pH范围内速率分布的斜率。

  DOI：

  10.1039/p29830000821

文献信息

• 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 New Route to 1,3-Diacyl-2,3-dihydro-1<i>H</i>-imidazoles
  作者：Martin Wolfgang Plath、Hans-Dieter Scharf、Gerhard Raabe、Carl Krüger

  DOI：10.1055/s-1990-27063

  日期：——

  Preparative amounts of the title compounds can be prepared in high purity by hydrogenation of the corresponding 1,3-diacyl- imidazolium salts with sodium borohydride. Structures are confirmed by spectroscopic methods and in two cases by X-ray structure determination.

  可以通过氢化相应的1,3-二酰基咪唑盐与氢化钠的反应制备出高纯度的标题化合物的制备量。其结构通过光谱方法确认，在两个案例中通过X射线结构测定进行了验证。
• Cost-efficient and user-friendly ¹⁷O/¹⁸O labeling procedures of fatty acids using mechanochemistry
  作者：Jessica Špačková、Charlyn Fabra、Guillaume Cazals、Marie Hubert-Roux、Isabelle Schmitz-Afonso、Ieva Goldberga、Dorothée Berthomieu、Aurélien Lebrun、Thomas-Xavier Métro、Danielle Laurencin

  DOI：10.1039/d1cc02165f

  日期：——

  mechanochemical procedures for 17O/18O-isotope labeling of fatty acids are reported: a carboxylic acid activation/hydrolysis approach and a saponification approach. The latter route allowed first-time enrichment of important polyunsaturated fatty acids (PUFAs) including docosahexaenoic acid (DHA). Overall, a total of 9 pure labeled products were isolated in high yields (≥80%) and with high enrichment levels

  报道了脂肪酸17 O/ 18 O-同位素标记的两种机械化学程序：羧酸活化/水解方法和皂化方法。后一种途径首次实现了重要的多不饱和脂肪酸（PUFA）的富集，包括二十二碳六烯酸（DHA）。总体而言，在温和的条件下，以高产率（≥80%）和高富集水平（≥37%的C=O和C-OH羧基氧原子平均标记）分离出总共9种纯标记产物，简而言之时间 （
• Hedgehog protein conjugate
  申请人：Curis, Inc.

  公开号：EP1557427A2

  公开（公告）日：2005-07-27

  A composition comprising hedgehog conjugate which is characterized in that it contains: a) a polypeptide composed of 10 to 30 hydrophobic amino acids and/or amino acids which form transmembrane helices and are positively charged, b) 1 to 4 aliphatic, saturated or unsaturated hydrocarbon residues with a chain length of 10 to 24 C atoms and with a hydrophobic action or c) a hydrophobic thio compound covalently bound to a hedgehog protein and a growth factor.

  一种由刺猬蛋白共轭物组成的组合物，其特征在于它含有：a) 由 10 至 30 个疏水氨基酸和/或形成跨膜螺旋并带正电荷的氨基酸组成的多肽，b) 1 至 4 个脂肪族、饱和或不饱和烃残基，链长为 10 至 24 个 C 原子，具有疏水作用，或 c) 与刺猬蛋白和生长因子共价结合的疏水硫代化合物。
• Active hedgehog protein conjugate
  申请人：——

  公开号：US20030139574A1

  公开（公告）日：2003-07-24

  A hedgehog conjugate which is characterized in that it contains: a) a polypeptide composed of 10 to 30 hydrophobic amino acids and/or amino acids which form transmembrane helices and are positively charged, b) 1 to 4 aliphatic, saturated or unsaturated hydrocarbon residues with a chain length of 10 to 24 C atoms and with a hydrophobic action or c) a hydrophobic thio compound covalently bound to a hedgehog protein and which has a several-fold increased activity and is suitable as a pharmaceutical agent.

  一种刺猬蛋白共轭物，其特征在于它包含：a) 由 10 至 30 个疏水氨基酸和/或形成跨膜螺旋并带正电荷的氨基酸组成的多肽，b) 1 至 4 个脂肪族、饱和或不饱和烃残基，链长为 10 至 24 个 C 原子，具有疏水作用，或 c) 与刺猬蛋白共价结合的疏水硫代化合物，其活性可提高数倍，适合用作药剂。