ethyl 3-oxohexadecanoate | 62148-72-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 3-oxohexadecanoate
• CAS: 62148-72-5
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: PXZGIZYCPLIFIX-UHFFFAOYSA-N

物化性质

• 沸点：
  165-170 °C(Press: 3 Torr)
• 密度：
  0.914±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-oxohexadecanoate 在 三乙烯二胺 、 lithium diisopropyl amide 作用下， 以 xylene 为溶剂， 反应 21.33h， 生成 N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-hexadecanamide
  参考文献：
  名称：

  Inhibitors of acyl-CoA:cholesterol acyltransferase. 5. Identification and structure-activity relationships of novel .beta.-keto amides as hypocholesterolemic agents

  摘要：

  A study of structure-activity relationships of substituted beta-ketoamide ACAT inhibitors I and II was performed. The results of this study suggest that whereas the beta-keto group was tolerated with no loss in activity, beta-hydroxy and oxime moieties led to significantly reduced activity in vitro and in vivo. The most potent inhibitor from the acyclic series (I) (11, IC50 = 0.006 muM) contained a C-13 alkyl chain. This compound reduced plasma total cholesterol by 38% and 66% at 3 and 30 mg/kg, respectively, in cholesterol-fed rats. Dimethylation alpha to the anilide core(5) and subsequent N-methylation of the amide NH (6) decreased in vitro potency significantly. It was also found that high potency was retained with inhibitors which incorporated the carbonyl into a lactam ring (II).

  DOI：

  10.1021/jm00072a014
• 作为产物：
  描述：

  肉豆蔻酰氯 在 乙醚 、 氨 作用下， 生成 ethyl 3-oxohexadecanoate
  参考文献：
  名称：

  Asano; Ohta, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1931, vol. 51, p. 397; dtsch. Ref. S. 36

  摘要：

  DOI：

文献信息

• Intermolecular ^2h<i>J</i>_NN Coupling in Multiply Hydrogen-Bonded Ureidopyrimidinone Dimers in Solution
  作者：Serge H. M. Söntjens、Marcel H. P. van Genderen、Rint P. Sijbesma

  DOI：10.1021/jo034889o

  日期：2003.11.1

  15N-Labeled ureido-4[1H]-pyrimidinones 4a and 5a were synthesized in order to investigate hydrogen bonding in the strongly hydrogen-bonded dimers in solution with intermolecular (2h)J(NN) coupling. Both direct-detection (15)N NMR and one-dimensional (15)N INADEQUATE (for smaller scalar coupling constants) were employed to determine the coupling constants. For dimers of 4 in CDCl(3), a temperature-dependent

  合成了15N标签的ureido-4 [1H]-嘧啶酮4a和5a，以研究分子间（2h）J（NN）偶联的溶液中强氢键二聚体中的氢键。直接检测（15）N NMR和一维（15）N INADEQUATE（用于较小的标量耦合常数）均用于确定耦合常数。对于CDCl（3）中4的二聚体，观察到温度依赖性（2h）J（NN），范围从+10摄氏度的2 Hz到-20摄氏度的5.1 Hz。在更慢交换双功能衍生物5的二聚体中，耦合常数可以在室温下通过反门控（1）H解耦的（15）N NMR实验确定。5a二聚体的不同异构体的偶联常数（4.96、5.13、4.37和5。如Del Bene等人（27 Hz）所用，以测试（2h）J（NN）值与NN距离之间的关系。借助于这种关系计算的NN距离与在5b的X射线晶体结构中观察到的距离显示出极好的一致性，特别是当考虑到氢键的非线性时。
• Identification of long chain alkylidenemalonates as novel small molecule modulators of histone acetyltransferases
  作者：Gianluca Sbardella、Sabrina Castellano、Caterina Vicidomini、Dante Rotili、Angela Nebbioso、Marco Miceli、Lucia Altucci、Antonello Mai

  DOI：10.1016/j.bmcl.2008.04.017

  日期：2008.5

  simplified analogue of anacardic acid, was identified as the first mixed activator/inhibitor of histone acetyltransferases (HATs). It potentiates PCAF HAT activity while inhibiting those of p300/CBP and recombinant CBP. The remarkable apoptotic effect together with the ability to selectively acetylate histone versus non-histone substrates appoint 1b as a lead for the development of anticancer drugs.

  戊二烯丙二酸戊二酸酯1b，一种简化的豆蔻酸类似物，被确定为组蛋白乙酰基转移酶（HATs）的第一种混合激活剂/抑制剂。它增强PCAF HAT活性，同时抑制p300 / CBP和重组CBP的活性。与非组蛋白底物相比，显着的凋亡作用以及选择性地乙酰化组蛋白的能力将1b列为开发抗癌药物的先导。
• Syntheses and antimicrobial activities of 3-acyltetramic acid derivatives.
  作者：KEIZO MATSUO、MASAHIDE KIMURA、TOSHIYUKI KINUTA、NORIKO TAKAI、KUNIYOSHI TANAKA

  DOI：10.1248/cpb.32.4197

  日期：——

  3-Acyltetramic acids having various substituents at the 1-and 5-positions, and possessing a tricarbonylmethane structure, were synthesized and tested for antimicrobial activity to investigate the structure-activity relationships. It was found that the nature of the substituents at the 1-and 5-positions as well as the 3-position is an important factor for activity to inhibit the growth of Bacillus subtillis and Staphylococcus aureus.

  合成了具有不同取代基的3-酰基四氟酸，并且具有三羰基甲烷结构，测试其抗菌活性以研究结构-活性关系。研究发现，1位和5位以及3位取代基的性质是抑制枯草芽孢杆菌和金黄色葡萄球菌生长活性的重要因素。
• Electronic substituent effects on hydrogen-bonding motifs modulate supramolecular polymerisation
  作者：Maria L. Pellizzaro、Julie Fisher、Andrew J. Wilson

  DOI：10.1039/c2ra22715k

  日期：——

  Hydrogen-bond assembled supramolecular polymers receive enormous interest as stimuli responsive materials that can be obtained using small easy to purify organic molecules. A key feature that determines materials properties in dilute solution is the strength of interaction between supramolecular synthons. In this work we illustrate that electronic substituents which are conjugated to the hydrogen-bonding motif can have subtle but significant effects on the degree of supramolecular polymerisation. Using ureidopyrimidines which contain electron donating phenolate and benzoate ester linkages in direct electronic communication with the self-complementary hydrogen-bonding motif, diffusion ordered spectroscopy (DOSY) demonstrates predictable differences in the extent of supramolecular polymerisation.

  氢键组装的超分子聚合物作为刺激响应材料受到了极大的关注，这种材料可以利用易于纯化的小型有机分子来获得。决定材料在稀溶液中特性的一个关键特征是超分子合成物之间的相互作用强度。在这项工作中，我们说明了与氢键基团共轭的电子取代基对超分子聚合度会产生微妙但重要的影响。利用脲基嘧啶（含有与自互补氢键基团直接电子通信的电子捐赠苯酚酯和苯甲酸酯连接），扩散有序光谱（DOSY）显示了超分子聚合程度的可预测差异。
• Synthesis and Antimicrobial Activity of Novel 4-Hydroxy-2-quinolone Analogs
  作者：Thitiphong Khamkhenshorngphanuch、Kittipat Kulkraisri、Alongkorn Janjamratsaeng、Napasawan Plabutong、Arsa Thammahong、Kanitta Manadee、Sarisa Na Pombejra、Tanatorn Khotavivattana

  DOI：10.3390/molecules25133059

  日期：——

  of substituent, has a dramatic impact on the antimicrobial activities. Particularly, the brominated analogs 3j with a nonyl side chain exhibited exceptional antifungal activities against A. flavus (half maximal inhibitory concentration (IC50) = 1.05 µg/mL), which surpassed that of the amphotericin B used as a positive control. The antibacterial activity against S. aureus, although not as potent, showed

  烷基喹诺酮已被证明是抗菌药物发现管道中的特殊支架。在这项研究中，合成了一系列新的 4-羟基-2-喹啉酮类似物，在 C-3 上含有长烷基侧链，在 C-6 和 C-7 位置上有广泛的取代基。研究了这些类似物对金黄色葡萄球菌、大肠杆菌和黄曲霉的抗菌和抗真菌活性。构效关系研究表明，烷基链的长度以及取代基的类型对抗菌活性有显着影响。特别是，具有壬基侧链的溴化类似物 3j 对黄曲霉表现出卓越的抗真菌活性（半数最大抑制浓度 (IC50) = 1.05 µg/mL），这超过了用作阳性对照的两性霉素 B。对金黄色葡萄球菌的抗菌活性虽然没有那么强，但表现出与抗真菌活性相似的趋势。数据表明，4-羟基-2-喹诺酮是进一步开发新抗菌剂，尤其是抗真菌治疗的有前途的框架。