1-(1-吡咯烷基)-1-十八烷酮 | 33707-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(1-吡咯烷基)-1-十八烷酮
• 英文名称: 1-(pyrrolidin-1-yl)octadecan-1-one
• 英文别名: 1-octadecanoylpyrrolidine；stearic acid pyrrolidide；stearoyl pyrrolidide；MQ-B₄；N-Octadecanoyl-pyrrolidin；Pyrrolidine, 1-stearoyl-；1-pyrrolidin-1-yloctadecan-1-one
• CAS: 33707-76-5
• 化学式: C₂₂H₄₃NO
• 分子量: 337.59
• InChiKey: AEBDOCOLSSICMC-UHFFFAOYSA-N

物化性质

• 保留指数：
  2742

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(1-吡咯烷基)-1-十八烷酮 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-十八烷基吡咯烷
  参考文献：
  名称：

  长烷基链酰胺，胺及其衍生物对犬round虫幼虫的杀线虫活性。

  摘要：

  检查了具有长烷基链的酰胺和胺对犬round虫第二阶段幼虫的杀线虫活性。在氮上具有较小取代基的长链酰基酰胺显示出更强的活性，环状胺酰胺的活性强于无环酰胺。在一系列同源酰胺中，活性取决于烷基链长：在最佳链长处达到最大值，而在较短和较长的同系物中均降低。通过使用双线性模型分析了同系物的活性与疏水性之间的关系。对于所有中性酰胺，提供最大活性的化合物的疏水性均相似，但分子中具有额外胺基的酰胺具有不同的值。具有长烷基链的叔胺及其盐也具有与相应酰胺相当的杀线虫活性。这些盐以低于其临界胶束浓度的浓度杀死幼虫，表明它们表现为杀线虫作用的单个分子。

  DOI：

  10.1248/cpb.40.3234
• 作为产物：
  描述：

  硬脂酸 在 硫酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 1-(1-吡咯烷基)-1-十八烷酮
  参考文献：
  名称：

  Antiproliferative activity of synthetic fatty acid amides from renewable resources

  摘要：

  In the work, the in vitro antiproliferative activity of a series of synthetic fatty acid amides were investigated in seven cancer cell lines. The study revealed that most of the compounds showed antiproliferative activity against tested tumor cell lines, mainly on human glioma cells (U251) and human ovarian cancer cells with a multiple drug-resistant phenotype (NCI-ADR/RES). In addition, the fatty methyl benzylamide derived from ricinoleic acid (with the fatty acid obtained from castor oil, a renewable resource) showed a high selectivity with potent growth inhibition and cell death for the glioma cell line-the most aggressive CNS cancer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.019

文献信息

• A Convenient Protocol for the Synthesis of Fatty Acid Amides
  作者：Jens Nolsøe、Silje Johansson、Tonje Johannessen、Christiane Ellefsen、Mali Ristun、Simen Antonsen、Trond Hansen、Yngve Stenstrøm

  DOI：10.1055/s-0037-1611939

  日期：2019.1

  Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical,

  已经从哺乳动物和植物来源报道了几类生物存在的脂肪酸酰胺。许多与哺乳动物来源的脂肪酸结合的酰胺表现出对个体受体的特异性激活。它们作为药理学工具或作为开发新疗法的先导化合物的潜力引起了人们极大的兴趣。因此，需要在不影响敏感功能的几何形状或位置的情况下，通过实用、高产和可扩展的协议来获取此类酰胺。满足所有这些要求的方案包括用羰基二咪唑 (CDI) 活化相应的酸，然后与所需的胺或其盐酸盐反应。已经以通常高产率制备了五十多种化合物。
• One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent
  作者：Cyrous O. Kangani、David E. Kelley

  DOI：10.1016/j.tetlet.2005.10.068

  日期：2005.12

  A mild and highly efficient one pot-one step condensation and/or condensation-cyclization of various acids to amides and/or oxazolines using Deoxo-Fluor reagents is described. Parallel syntheses of various free fatty acids with 2-amino-2, 2-dimethyl-1-propanol resulted with excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Aliphatic pyrrolidine amides from two tropical convolvulaceous species
  作者：Britta Tofern、Petra Mann、Macki Kaloga、Kristina Jenett-Siems、Ludger Witte、Eckart Eich

  DOI：10.1016/s0031-9422(99)00245-9

  日期：1999.12

  Seven aliphatic pyrrolidine amides with branched and linear saturated C-15-C-19 acyl moieties were detected in vegetative plant organs of Ipomoea aquatica and Merremia quinquefolia as well as in seeds of M. quinquefolia by GC-MS analysis. One of the compounds was isolated from both species and characterized, as 1-(14-methylhexadecanoyl)pyrrolidine, a new natural product. The presence of 1-hexadecanoylpyrrolidine and 1-octadecanoylpyrrolidine was confirmed by comparison of their GC-MS data with those of synthesized compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Triazolopyridine, a new derivative for the structural determination of fatty acids by gas chromatography/mass spectrometry
  作者：Walter Vetter、Walter Meister、Gottfried Oesterhelt

  DOI：10.1002/oms.1210230803

  日期：1988.8

  AbstractTriazolopyridine is proposed as a new derivative for the location of branches and double bonds in fatty acids. It is compared with previously used derivatives and found to be clearly superior to the pyrrolidide and slightly superior to the β‐picolinyl ester with regard to the structure‐specific fragmentation pattern. It is prepared by reacting the activated acid with 2‐hydrazinopyridine followed by cyclization.
• VETTER, WALTER;WALTHER, WILLI, J. CHROMATOGR., 513,(1990) C. 405-407
  作者：VETTER, WALTER、WALTHER, WILLI

  DOI：——

  日期：——

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