N-十四烷基-2-吡咯烷酮 | 7261-72-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-十四烷基-2-吡咯烷酮
• 英文名称: N-tetradecyl-ethylenediamine
• 英文别名: N-Tetradecyl-aethylendiamin；N-tetradecyl ethylenediamine；N-Tetradecylethylendiamin；N'-tetradecylethane-1,2-diamine
• CAS: 7261-72-5
• 化学式: C₁₆H₃₆N₂
• 分子量: 256.475
• InChiKey: QIBKKTQVKFEWCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-O-(2,3-Epoxypropyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 、 N-十四烷基-2-吡咯烷酮 在 氯化铵 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以52%的产率得到6-O-[(R,S)-N-(2-tetradecylamino)(ethylamino)propan-2-ol]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis and evaluation of antibacterial and antitumor activities of new galactopyranosylated amino alcohols

  摘要：

  Three series of D-galactose derivatives linked to a lipophilic aminoalcohol moiety were synthesized and their antibacterial activity was evaluated against Mycobacterium tuberculosis and representative species of Gram positive and Gram negative bacteria. Five out of the thirteen tested compounds displayed activity against M. tuberculosis, with a minimal inhibitory concentration (MIC) of 12.5 mu g/mL and seven compounds were active against the four bacterial strains tested. The best results were obtained for amino alcohols 10 and 11 against Staphylococcus epidermidis (MIC = 2 mu g/mL). The antitumor activity was evaluated against three tumor cell lines (MCF-7, HeLa and MO59J) and compared to the normal cell line GM07492A. The results showed that the lowest IC50 values were observed for the amino alcohol 16 against MCF-7 (11.9 mu M) and MO59J (10.0 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.037
• 作为产物：
  描述：

  氯代十四烷 、 乙二胺 以 乙醇 为溶剂， 反应 24.0h， 以89%的产率得到N-十四烷基-2-吡咯烷酮
  参考文献：
  名称：

  Synthesis and evaluation of antibacterial and antitumor activities of new galactopyranosylated amino alcohols

  摘要：

  Three series of D-galactose derivatives linked to a lipophilic aminoalcohol moiety were synthesized and their antibacterial activity was evaluated against Mycobacterium tuberculosis and representative species of Gram positive and Gram negative bacteria. Five out of the thirteen tested compounds displayed activity against M. tuberculosis, with a minimal inhibitory concentration (MIC) of 12.5 mu g/mL and seven compounds were active against the four bacterial strains tested. The best results were obtained for amino alcohols 10 and 11 against Staphylococcus epidermidis (MIC = 2 mu g/mL). The antitumor activity was evaluated against three tumor cell lines (MCF-7, HeLa and MO59J) and compared to the normal cell line GM07492A. The results showed that the lowest IC50 values were observed for the amino alcohol 16 against MCF-7 (11.9 mu M) and MO59J (10.0 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.037

文献信息

• Combinatorial Synthesis and High-Throughput Screening of Alkyl Amines for Nonviral Gene Delivery
  作者：Linxian Li、Fengjian Wang、Yihang Wu、Gary Davidson、Pavel A. Levkin

  DOI：10.1021/bc400158w

  日期：2013.9.18

  method based on an alkylation of amines, allowing for the fast parallel synthesis of libraries of cationic lipid-like molecules (lipidoids). We exploited the method to synthesize 200 lipidoids, which were screened for their transfection efficiency in HEK293T cells. The screen resulted in about 2% of new lipidoids capable of efficient cell transfection similar or higher than the efficiency of Lipofectamine

  质粒DNA和siRNA高效传递到细胞中对于生物学和生物医学研究至关重要。尽管为开发有效的非病毒载体，例如阳离子脂质和聚合物，已经做出了巨大的努力，但是大多数载体需要多步合成，这使得这种载体的快速结构优化和组合合成变得复杂。在这里，我们提出了一种基于胺烷基化的简便，单步方法，可以快速并行合成阳离子脂质样分子（类脂质）的文库。我们利用该方法合成了200个类脂质，筛选了它们在HEK293T细胞中的转染效率。筛选后，大约有2％的新型脂质能够有效转染细胞，其效率与Lipofectamine 2000相似或更高。此外，
• Process of preparation of heterocyclic compounds employing acetylene ethers
  申请人：ORGANON

  公开号：US02813862A1

  公开（公告）日：1957-11-19

  The invention comprises compounds of the formula <;FORM:0785373/IV (a)/1>; wherein R is a -(CH2)6- or <;FORM:0785373/IV (a)/2>; group and R2 is hydrogen, alkyl, aryl or aralkyl. It comprises also a process for the preparation of compounds of the formula <;FORM:0785373/IV (a)/3>; wherein X is O, S, NH or NR3 (R3 is an alkyl, aryl or aralkyl group), by reacting a compound of the formula R1OC­C-R2, wherein R1 is an alkyl group, with a compound of the formula H2N-R-XH. The reaction is suitably carried out by allowing an alkoxyacetylene, such as an ethoxyacetylene compound, to react with an aminoalcohol, a diamine or a mercaptoamine. Examples describe the preparation according to the above process of (1) 2-methyl-oxazoline; (2) 2 : 4-dimethyl-oxazoline; (3) 2-methylimidazoline; (4) 2-methylbenzimidazole; (5) 2-methylthiazoline; (6) 2-methyl-1-dodecylimidazoline-2; (7) 2-propyl-imidazoline-2; (8) 2-benzylimidazoline-2; (9) 2-methyl- D 2-dihydro-oxazine - 1 : 3; (10) 2 - methyl - 3 : 4 : 5 : 6 - tetrahydropyrimidine; (11) 2-methyl-4 : 5-benzooxazine-1 : 3; (12) 2-methyl-5 : 6-dihydro-1 : 3-thiazine; (13) 2-(1-naphthylmethyl)-2-imidazoline; (14) 2-heptadecyl-2-imidazoline; (15) 2-methyl - 4 : 5 : 6 : 7 - tetrahydro - 1 : 3 - diazepine and (16) 2-methyl-4 : 5 : 6 : 7 : 8 : 9-hexahydro-1 : 3-oxazonine.

  这项发明包括以下公式的化合物：<;FORM:0785373/IV (a)/1>;其中R是一个-(CH2)6-或<;FORM:0785373/IV (a)/2>;基团，R2是氢、烷基、芳基或芳基烷基。它还包括一种制备以下公式的化合物的方法：<;FORM:0785373/IV (a)/3>;其中X是O、S、NH或NR3（R3是烷基、芳基或芳基烷基），通过将公式R1OC­C-R2的化合物（其中R1是烷基）与公式H2N-R-XH的化合物反应。反应通常通过允许烷氧基乙炔，如乙氧基乙炔化合物，与氨醇、二胺或巯胺反应来进行。示例描述了根据上述过程制备的化合物（1）2-甲基噁唑烷；（2）2 : 4-二甲基噁唑烷；（3）2-甲基咪唑烷；（4）2-甲基苯并咪唑；（5）2-甲基噻唑烷；（6）2-甲基-1-十二烷基咪唑-2；（7）2-丙基咪唑-2；（8）2-苄基咪唑-2；（9）2-甲基- D 2-二氢噁啉 - 1 : 3；（10）2-甲基-3 : 4 : 5 : 6-四氢嘧啶；（11）2-甲基-4 : 5-苯噁啉-1 : 3；（12）2-甲基-5 : 6-二氢-1 : 3-噻嗪；（13）2-(1-萘甲基)-2-咪唑烷；（14）2-庚十七烷基-2-咪唑烷；（15）2-甲基-4 : 5 : 6 : 7-四氢-1 : 3-二氮杂环己烷和（16）2-甲基-4 : 5 : 6 : 7 : 8 : 9-六氢-1 : 3-噁唑烷。

• Environmentally responsive adsorption and assembly behaviors from N-alkyl-1,2-ethylenediamines
  作者：Yi Yang、Jinfeng Dong、Bo Cai、Zan Jiang、Li Cheng、Xuefeng Li

  DOI：10.1039/c2sm27288a

  日期：——

  A series of pH sensitive single-tailed surfactants, N-alkyl-1,2-ethylenediamine (CmN2N, where m = 8, 10, 12, 14, 16), were synthesized and characterized. The adsorption and aggregation properties of them were determined by equilibrium surface tension, static and dynamic light scattering (SLS and DLS), rheology, and cryogenic transmission electron microscopy (cryo-TEM) techniques in detail. It was found that both the surface activity and self-assembly behavior of CmN2N were strongly dependent on the solution pH, owing to the protonation state of amino groups in CmN2N. When at least one of the amino groups of CmN2N was protonated the logarithm of the critical micelle concentration (cmc) followed the well-known Klevens equation, i.e. cmc decreased linearly with the increase of hydrocarbon chain length. Simultaneously, the surface adsorption area per molecule (Amin) was decreased for each CmN2N when the solution pH varied from acidic to basic conditions. The pH-dependent micelle to vesicle transition was universally observed in the bulk phase of CmN2N. More interestingly, the rodlike micelles formed in C10N2N, C12N2N and C14N2N could transform into vesicles reversibly upon heating or cooling, which indicated the thermal sensitivityof organized assemblies, whereas not in C8N2N and C16N2N.

  合成并表征了一系列对 pH 值敏感的单尾表面活性剂 N-烷基-1,2-乙二胺（CmN2N，其中 m = 8、10、12、14、16）。通过平衡表面张力、静态和动态光散射（SLS 和 DLS）、流变学和低温透射电子显微镜（cryo-TEM）技术详细测定了它们的吸附和聚集特性。研究发现，由于 CmN2N 中氨基的质子化状态，CmN2N 的表面活性和自组装行为都与溶液的 pH 值密切相关。当 CmN2N 中至少有一个氨基被质子化时，临界胶束浓度（cmc）的对数遵循著名的 Klevens 方程，即 cmc 随烃链长度的增加而线性降低。同时，当溶液的 pH 值从酸性变为碱性时，每种 CmN2N 的每分子表面吸附面积（Amin）都会减小。在 CmN2N 的体相中普遍观察到了与 pH 值相关的胶束到囊泡的转变。更有趣的是，在 C10N2N、C12N2N 和 C14N2N 中形成的棒状胶束在加热或冷却时可逆地转变为囊泡，这表明了有组织组装体的热敏感性，而在 C8N2N 和 C16N2N 中则没有这种现象。
• Synthesis, Structure, and Stereochemistry of Double-Chain Surfactant Co(III) Complexes
  作者：Navamoney Arulsamy、D. Scott Bohle、Patricia A. Goodson、David A. Jaeger、Ven B. Reddy

  DOI：10.1021/ic000839f

  日期：2001.2.1

  Double-chain surfactant octahedral Co(III) complexes 1 and 2 (X = ClO4) (a, R = C6H13; b, R = C8H17; c, R = C10H21; d, R = C12H25; e, R = C14H29; f, R = C16H33) were synthesized in H2O and 20:1 (v/v) EtOH−H2O by the reaction of RNHCH2CH2NH2 (5) with Na3Co(NO2)6, followed by the addition of NaClO4. The cisoid 1/transoid 2 diastereomer ratio increased upon going from EtOH−H2O to H2O, in particular by

  双链表面活性剂八面体 Co(III) 配合物 1 和 2 (X = ClO4) (a, R = C6H13; b, R = C8H17; c, R = C10H21; d, R = C12H25; e, R = C14H29; f , R = C16H33) 在 H2O 和 20:1 (v/v) EtOH-H2O 中通过 RNHCH2CH2NH2 (5) 与 Na3Co(NO2)6 反应合成，然后加入 NaClO4。当从 EtOH-H2O 变为 H2O 时，顺式 1/反式 2 非对映异构体的比率增加，特别是辛基和十二烷基系统增加了 ≈5 倍，十六烷基系统增加了 ≈8 倍。cisoid 1 相对量的增加归因于与配体 5 在 H2O 中的聚集相关的疏水效应。表面活性剂配合物 3 和 4 (X = NO3) 也在 EtOH(MeOH)-H2O 中制备。1-4 的表征包括 1e 和 3a 的单晶 X
• Process for preparing organo-nitrogen grafted copolymers, the copolymers so produced and mineral oil compositions containing them
  申请人：PHILLIPS PETROLEUM COMPANY

  公开号：EP0001547A1

  公开（公告）日：1979-05-02

  Nitrogen-containing copolymers are prepared by the reaction of lithiated hydrogenated conjugated dienemonovinylarene copolymers with nitrogen containing organic compounds. The nitrogen-containing copolymers are oil additives which combine the aspects of viscosity index improvers with dispersant properties.

  含氮共聚物是由石化氢化共轭二烯月桂烯共聚物与含氮有机化合物反应制备而成。含氮共聚物是一种油品添加剂，兼具粘度指数改进剂和分散剂的特性。