n-hexadecyl isocyanide | 125192-26-9

• 英文名称: n-hexadecyl isocyanide
• 英文别名: 1-Isocyanohexadecane
• CAS: 125192-26-9
• 化学式: C₁₇H₃₃N
• 分子量: 251.456
• InChiKey: MVPDBJNITWNXKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  4.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  n-hexadecyl isocyanide 、 N-甲基苯胺 在 selenium 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以73%的产率得到N'-n-hexadecyl-N-methyl-N-phenylselenourea
  参考文献：
  名称：

  A Library of Selenourea Precursors to PbSe Nanocrystals with Size Distributions near the Homogeneous Limit

  摘要：

  We report a tunable library of N,N,N'-trisubstituted selenourea precursors and their reaction with lead oleate at 60-150 degrees C to form carboxylate-terminated PbSe nanocrystals in quantitative yields. Single exponential conversion; kinetics can be tailored over 4 orders of magnitude by adjusting the selenourea structure. The wide range of conversion reactivity allows the extent of nucleation ([nanocrystal] = 4.6-56.7 mu M) and the size following complete precursor conversion (d = 1.7-6.6 nm) to be controlled. Narrow size distributions (sigma = 0.5-2%) are obtained whose spectral line widths are dominated (73-83%) by the intrinsic single particle spectral broadening, as observed using spectral hole burning measurements. The intrinsic broadening decreases with increasing size (fwhm = 320-65 meV, d = 1.6-4.4 nm) that derives from exciton-phonon structure and exciton phonon coupling rather than broadening caused by the size distribution.

  DOI：

  10.1021/jacs.6b11021
• 作为产物：
  描述：

  十六胺 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 n-hexadecyl isocyanide
  参考文献：
  名称：

  Diversification of a Novel α‐Galactosyl Ceramide Hotspot Boosts the Adjuvant Properties in Parenteral and Mucosal Vaccines

  摘要：

  摘要开发强效佐剂是提高亚单位疫苗性能的重要一步。CD1d激动剂，如典型的α-半乳糖基神经酰胺（α-GalCer），因其能激活iNKT细胞并引发树突状细胞快速成熟和B细胞活化而备受关注。在这里，我们介绍了α-GalCer 骨架上的一个新型衍生热点，即酰胺键上的 N-取代基。这种以前未曾探索过的糖脂化学型空间的多组分多样化允许引入各种额外的官能团，这些官能团既可以增强佐剂特性，也可以作为进一步与抗原共轭的处理剂，以开发自佐剂疫苗。通过这一策略，我们发现了一些化合物，与已知的强效 CD1d 激动剂相比，这些化合物在通过肠外或粘膜途径给药时能增强对抗原特异性 T 细胞的刺激并提高抗体反应。值得注意的是，在鼻内免疫后，各种官能化的α-GalCer类似物比以前为此目的优化过的PEG化α-GalCer类似物显示出更强的佐剂效应。最终，这项工作将为使用粘膜疫苗预防微生物感染开辟多种途径。

  DOI：

  10.1002/anie.202310983

文献信息

• Combined Ugi-4CR/CuAAC Approach to Triazole-Based Neoglycolipids
  作者：Karell Pérez-Labrada、Ignacio Brouard、Inmaculada Méndez、Carlos S. Pérez、José A. Gavín、Daniel G. Rivera

  DOI：10.1002/ejoc.201402117

  日期：2014.6

  New glycolipids that feature a carbohydrate/triazole/lipid hybrid architecture were readily produced by a combined multicomponent/click approach. The process comprises the use of the Ugi four-component reaction to construct double-lipidic scaffolds that have either alkyne or azide functionalities followed by conjugation to mono- and trisaccharides through a CuI-catalyzed 1,3-dipolar cycloaddition (click)

  具有碳水化合物/三唑/脂质混合结构的新糖脂很容易通过组合多组分/点击方法生产。该过程包括使用 Ugi 四组分反应构建具有炔烃或叠氮化物官能团的双脂支架，然后通过 CuI 催化的 1,3-偶极环加成（点击）过程与单糖和三糖结合。整个过程的高化学效率和可行性为这种独特的 Ugi/click 糖脂类库的快速创建和生物筛选提供了新的机会。进行动态核磁共振实验以评估与这些化合物中顺式/反式酰胺键的异构化相关的活化自由能。
• Substituted imidazo[1,2-a]pyridine compounds and pharmaceutical preparations containing substituted imidazo[1,2-a]pyridine compounds
  申请人：Sundermann Bernd

  公开号：US20070099896A1

  公开（公告）日：2007-05-03

  Substituted imidazo[1,2-a]pyridine compounds, a process for the production thereof, pharmaceutical preparations containing such compounds and methods of using such substituted imidazo[1,2-a]pyridine compounds to treat and/or inhibit various diseases or pathological conditions.

  取代的咪唑[1,2-a]吡啶化合物，其生产方法，含有这种化合物的药物制剂，以及使用这种取代的咪唑[1,2-a]吡啶化合物来治疗和/或抑制各种疾病或病理条件的方法。
• Cationic lipids <i>via</i> multi-component Passerini reaction for non-viral gene delivery
  作者：Rong Wang、Jin Li、Jia-Jia Chen、Yu Guo、Yue Hu、Xiao-Qi Yu、Ji Zhang

  DOI：10.1039/d3nj05949a

  日期：——

  toward the lipid molecules with variable product structures for structure–activity relationship studies. The LNPs formed from these lipids could compress DNA efficiently and form stable lipoplexes with low cytotoxicity. The gene transfection efficiency was largely affected by the lipid structure including the cationic headgroup and hydrophobic tails. The lipids A3 with equal C14 length tails could induce

  脂质纳米粒子（LNP）是最先进的非病毒核酸递送平台，在临床治疗中具有巨大的应用潜力。但仍存在合成路线复杂、合成收率低、成本高等缺点。本研究通过Passerini反应设计并制备了一系列具有不同阳离子头基和疏水尾部的脂质分子，为具有可变产物结构的脂质分子的构效关系研究提供了一种便捷的多组分一步合成工艺。 。由这些脂质形成的LNP可以有效地压缩DNA并形成具有低细胞毒性的稳定的脂质复合物。基因转染效率很大程度上受脂质结构的影响，包括阳离子头基和疏水尾部。具有相同C14长度尾部的脂质A3可以诱导最高的转染效率，比Lipo 2000高出25倍。与商业转染试剂相比，目标LNP的效率受血清的负面影响较小。通过共聚焦显微镜和流式细胞术进行的机制研究表明，具有相同 C14 长度尾部的脂质可导致更有效的细胞摄取，这可能有助于其更高的转染效率。该研究为通过多组分Passerini反应构建用于非病毒基因递送的阳离子脂质基因载体提供了新策略。
• Multicomponent Synthesis of Ugi-Type Ceramide Analogues and Neoglycolipids from Lipidic Isocyanides
  作者：Karell Pérez-Labrada、Ignacio Brouard、Inmaculada Méndez、Daniel G. Rivera

  DOI：10.1021/jo300462m

  日期：2012.5.18

  Unique types of ceramide and glycolipid architectures were obtained by means of Ugi reactions incorporating lipidic isocyanides as surrogates of sphingolipids. The multicomponent nature of this approach allowed for a highly efficient assembly process, wherein two of the components provided the lipidic tails while a third one incorporated either the functionality suitable for the conjugation to sugar or the sugar moiety itself. Two dissimilar strategies were implemented: (i) the initial assembly of ceramide analogues followed by glycosylation to produce a glycolipid skeleton and (ii) the one-pot construction of glycolipid frameworks by condensation of lipidic isocyanides either with lipidic amines and oligosaccharidic acids or with fatty acids and oligosaccharidic amines. Whereas both approaches are amenable for accessing analogues of anticancer glycolipids, the latter one proved to have greater potential owing to its more straightforward and efficient character. Overall, the methodology developed shows great promise toward the massive (eventually combinatorial) production of neoglycolipids suitable for biological screening.
• Jungermann; Smith, Journal of the American Oil Chemists' Society, 1959, vol. 36, p. 388,389
  作者：Jungermann、Smith

  DOI：——

  日期：——