3-oxoundecanoic acid | 4435-85-2

• 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: 3-oxoundecanoic acid
• 英文别名: 3-oxo-undecanoic acid；3-Oxo-undecansaeure
• CAS: 4435-85-2
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: RYAXOIRSQGWHQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxoundecanoic acid 在 potassium dihydrogenphosphate 、 baker's yeast 、 葡萄糖 作用下， 以 乙醚 、 水 为溶剂， 反应 9.0h， 生成 (R)-methyl 3-hydroxyundecanoate
  参考文献：
  名称：

  Asymmetric reduction of aliphatic short- to long-chain .beta.-keto acids by use of fermenting bakers' yeast

  摘要：

  DOI：

  10.1021/jo00299a041
• 作为产物：
  描述：

  methyl 3-oxoundecanoate 在 盐酸 、 sodium methylate 作用下， 生成 3-oxoundecanoic acid
  参考文献：
  名称：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

  摘要：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00150-7

文献信息

• Design and Synthesis of 2-Alkylpyrimidine-4,6-diol and 6-Alkylpyridine-2,4-diol as Potent GPR84 Agonists
  作者：Yang Liu、Qing Zhang、Lin-Hai Chen、Hui Yang、Wei Lu、Xin Xie、Fa-Jun Nan

  DOI：10.1021/acsmedchemlett.6b00025

  日期：2016.6.9

  A series of alkylpyrimidine-4,6-diol derivatives were designed and synthesized as novel GRP84 agonists based on a high-throughput screening (HTS) hit 1. 6-Nonylpyridine-2,4-diol was identified as the most potent agonist of GPR84 reported so far, with an EC50 of 0.189 nM. These novel GPR84 agonists will provide valuable tools for the study of the physiological functions of GPR84.

  基于高通量筛选（HTS）hit 1，设计并合成了一系列烷基嘧啶-4,6-二醇衍生物，作为新型GRP84激动剂。6-壬基吡啶-2,4-二醇被鉴定为迄今为止报道的最强效的GPR84激动剂，EC 50为0.189 nM。这些新颖的GPR84激动剂将为研究GPR84的生理功能提供有价值的工具。
• Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs
  作者：Leah M. Bouthillette、Catherine A. Darcey、Tess E. Handy、Sarah C. Seaton、Amanda L. Wolfe

  DOI：10.1016/j.bmcl.2017.04.067

  日期：2017.6

  for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50=0.04-3.8µg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50=223-304µg/mL)

  天然产物是具有抗菌活性的结构多样的化合物的丰富来源，可用于开发新型有效的抗生素。一类这样的天然产物是假吡喃酮。在这里，我们介绍了从北卡罗莱纳州西部花园土壤中发现的假单胞菌属物种中分离出假吡喃酮B（2），以及对天然产物的C3和C6烷基类似物对革兰氏阳性和革兰氏阴性细菌的抗菌活性的SAR评估。我们发现抗菌活性和C3 / C6烷基链长之间存在直接关系。为了抑制革兰氏阳性菌，发现6​​至7个碳原子之间的烷基链长度最活跃（IC50 = 0.04-3.8µg / mL），而短链烷基类似物对革兰氏阴性菌的活性中等（IC50 = 223） -304µg / mL）。
• Modifizierte Alkoxylierungsprodukte, die zumindest eine nicht-terminale Alkoxysilylgruppe aufweisen, mit erhöhter Lagerstabilität und verbesserter Dehnung und der unter deren Verwendung hergestellten Polymere
  申请人：Evonik Degussa GmbH

  公开号：EP3050910A1

  公开（公告）日：2016-08-03

  Gegenstand der vorliegenden Erfindung sind spezielle Alkoxylierungsprodukte, ein Verfahren zu deren Herstellung, Zusammensetzungen, die diese Alkoxylierungsprodukte enthalten, sowie deren Verwendung.

  本发明涉及特种烷氧基化产品、其制备工艺、含有这些烷氧基化产品的组合物及其用途。
• Breusch; Keskin, Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya, 1946, vol. 11, p. 26
  作者：Breusch、Keskin

  DOI：——

  日期：——
• Inhibition of human sputum elastase by substituted 2-pyrones. 2
  作者：Luisa Cook、Bela Ternai、Peter Ghosh

  DOI：10.1021/jm00389a010

  日期：1987.6

  Nineteen 4-hydroxy- and 4-methoxy-2-pyrones related to elasnin (I) have been assayed for in vitro inhibition of human sputum elastase (HSE), porcine pancreatic elastase, alpha-chymotrypsin, and trypsin. Inhibition is reported as Ki and Ki'; percentage inhibition was dependent on [S] in a number of cases, making it unsuitable as a measure of relative inhibition. The 3-(1-oxoalkyl)-4-hydroxy-6-alkyl-2-pyrones were found to be most effective, the octyl homologue 11 being the most potent inhibitor (Ki = 4.6 microM, 30 times better than the lead compound). A further reduction in inhibition was observed when the hitherto hydrophobic 6-substituent was substituted by a branched functionality of hydrophilic nature. Conversely, methylation of the 4-hydroxy group of the 6-alkyl-2-pyrones increased inhibitory activity. The mechanism of inhibition varied from pure noncompetitive to mixed type to uncompetitive and was found to be dependent on the pattern of substitution. We believe that the 4-hydroxy-2-pyrone binds to the S4 subsite, with the 6-substituent extending across the S4-S1 subsites and the 3-substituent occupying the S5 subsite. The length of the inhibitor binding region was calculated to be approximately 24 A. None of the hydrophobic compounds were found to have any appreciable inhibition (less than 10%) with porcine pancreatic elastase, bovine alpha-chymotrypsin, and bovine trypsin when tested at the limit of their solubility. The hydrophilic compounds were nonspecific, inhibiting all four enzymes. Dialysis was used to show that the interaction is fully reversible.

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