3β-cholest-5-en-3-yl-N-(3-aminopropyl)carbamate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-cholest-5-en-3-yl-N-(3-aminopropyl)carbamate
• 英文别名: (3S)-3-O-[N-(3-aminopropyl)carbamoyl]cholesterol；3β-cholest-5-en-3-yl N-(2-aminopropyl)carbamate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-(3-aminopropyl)carbamate
• 化学式: C₃₁H₅₄N₂O₂
• 分子量: 486.782
• InChiKey: ONMRMXAUUUSNCK-GTPODGLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-cholest-5-en-3-yl-N-(3-aminopropyl)carbamate 在 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[3-[[4-[2-[2-(1,3-dithiol-2-ylidene)-1,3-dithiol-4-yl]ethynyl]benzoyl]amino]propyl]carbamate
  参考文献：
  名称：

  Organogelators Based on TTF Supramolecular Assemblies: Synthesis, Characterization, and Conductive Property

  摘要：

  A closely related family of organogelators 1-2 appended one or two electroactive tetrathiafulvalene (TTF) residues, has been designed and readily synthesized by Sonogashira reactions. These compounds can gelate a variety of organic solvents in view of multiple intermolecular interactions, and compounds 2 with two TTF subunits exhibit higher gelation ability than their corresponding 1. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) investigation of the xerogels from toluene gave a visual image showing that fibrillar aggregates are entangled in three-dimensional network structures. The columnar TTF cores stacking in the fiber, evidenced by the mixed-valence states absorption at around 2000 nm in ultraviolet visible near-infrared (UV-vis-NIR) spectra, provide an efficient pathway for the electron conduction. Upon oxidized by iodine, these xerogels exhibit semiconductive behaviors with moderate levels of conductivity. Additionally, the electrical conductivity of doped-xerogels 2 is 1 order of magnitude higher than that of 1 under identical conditions.

  DOI：

  10.1021/la103686n
• 作为产物：
  描述：

  胆固醇甲酰氯 、 1,3-丙二胺 以 二氯甲烷 为溶剂， 反应 4.0h， 以92%的产率得到3β-cholest-5-en-3-yl-N-(3-aminopropyl)carbamate
  参考文献：
  名称：

  极性头基和间隔基长度对基于胆固醇的阳离子脂质 DNA 转染的影响

  摘要：

  本文涉及阳离子脂质的头基和间隔长度对转染效率的影响。为了开发高效阳离子脂质，合成了一系列具有三种不同头基（铵、三甲基铵和胍）的二价赖氨酸-二胺缀合胆固醇基阳离子脂质。新合成的阳离子脂质 ( 1-6 ) A在存在和不存在两性离子辅助脂质 DOPE（二油酰磷脂酰乙醇胺）的情况下形成阳离子脂质体。凝胶阻滞测定表明，大多数制备的脂质复合物可以在 DOPE 存在的情况下阻滞 DNA 迁移。我们尝试修饰不同的阳离子头基以提高转染效率。然而，具有未修饰的赖氨酸头基的二价铵的赖氨酸-1,3-二氨基丙烷缀合的胆固醇基脂质4A在HEK293中表现出较高的相对转染效率。当用 DOPE（1:1 重量比）配制4A的转染效率时，与市售转染剂 Lipofectamine™ 2000 (L2k) 相比，其产生相同的范围。研究脂质4A以优化脂质/DOPE 和 DNA/脂质比率以及 DNA 量的条件。还研究了高效脂质4A的转染效率，以确定

  DOI：

  10.1039/c9md00459a

文献信息

• Strength Enhancement of Nanostructured Organogels through Inclusion of Phthalocyanine-Containing Complementary Organogelator Structures and In Situ Cross-Linking by Click Chemistry
  作者：David Díaz Díaz、Juan José Cid、Purificación Vázquez、Tomás Torres

  DOI：10.1002/chem.200800714

  日期：2008.10.20

  Stable photoactive organogels were successfully prepared by a two-step sequence involving: 1) formation of thermoreversible organogels by use of a combination of low-molecular-weight organogelators (LMOGs) and ZnII-phthalocyanine (ZnII-Pc) moieties containing complementary organogelator structures, and 2) strength enhancement of the gels by in situ cross-linking with the aid of CuI-catalysed azide-alkyne

  稳定的光敏有机凝胶可通过两步顺序成功制备，该过程包括：1）通过结合使用低分子量有机胶凝剂（LMOG）和含有互补有机胶凝剂结构的ZnII-酞菁（ZnII-Pc）部分的组合来形成热可逆有机凝胶， 2）借助于CuI催化的叠氮化物-炔烃[3 + 2]环加成物（CuAAC）通过原位交联来增强凝胶的强度。相对于有机胶凝剂体系[LMOG + ZnIIPc]，低比例添加的柔性C6脂族二叠氮化物和合适的二炔（摩尔比1：1）之间进行了最佳点击反应。将二炔单元以还可以参与[LMOG + ZnIIPc]的自组装的方式掺入到类似于LMOGs结构的分子中。多组分光敏有机凝胶对通过CuAAC进行这种增强的显着相容性使其溶胶-凝胶转变温度（Tgel）最高提高了15摄氏度。通过“逆流法”估算的Tgel值相符通过差示扫描量热法（DSC）获得的值。流变学测量证实了所有含Pc凝胶的粘弹性，刚性和脆性。透射和扫描电子显微镜（TEM
• Simple design but marvelous performances: molecular gels of superior strength and self-healing properties
  作者：Zhiyan Xu、Junxia Peng、Ni Yan、Hang Yu、Shasha Zhang、Kaiqiang Liu、Yu Fang

  DOI：10.1039/c2sm27208c

  日期：——

  Four nitrobenzoxadiazole (NBD)-containing cholesteryl (Chol) derivatives were prepared, and their gelation behaviors were tested. It was demonstrated that the compounds show a remarkable gelling ability. In particular, a subtle change in the length of the spacers connecting the two structural units of the compounds, which are NBD and Chol, respectively, produced a dramatic change in the gelation ability and the gel properties of the compounds. As for gelation, compound 1 is much more powerful than others, especially in the gelation of methanol-containing organic mixtures. It is to be noted that the gel of 1/pyridine–methanol exhibits superior mechanical strength with a yield stress higher than 6300 Pa at a gelator concentration of 2.5% (w/v), and the value exceeds 23 000 Pa when the gelator concentration reaches 5.0% (w/v), a result never reported before in the field of molecular gels based on low-molecular mass gelators (LMMGs). More importantly, the gel shows a rapid self-healing property as evidenced by the fact that the gel heals up immediately upon cutting, provided the segments from the cutting are squeezed together. No doubt, our findings establish a benchmark for LMMG-based molecular gels in their rheological performances. FTIR, 1H NMR and XRD studies revealed that intermolecular hydrogen bonding and π–π stacking are two of the main driving forces to promote the gelation of the system and the self-assembling of the molecules of the gelator.

  研究人员制备了四种含硝基苯并噁二唑（NBD）的胆固醇（Chol）衍生物，并测试了它们的凝胶行为。结果表明，这些化合物具有显著的胶凝能力。特别是，连接化合物两个结构单元（分别为 NBD 和 Chol）的间隔物的长度发生微妙变化，化合物的凝胶能力和凝胶特性就会发生巨大变化。在凝胶化方面，化合物 1 的凝胶化能力远远强于其他化合物，尤其是在含甲醇有机混合物的凝胶化方面。值得注意的是，1/吡啶-甲醇的凝胶显示出卓越的机械强度，在凝胶剂浓度为 2.5%（w/v）时，屈服应力高于 6300 Pa，当凝胶剂浓度达到 5.0%（w/v）时，屈服应力超过 23 000 Pa，这在基于低分子质量凝胶剂（LMMGs）的分子凝胶领域是从未报道过的。更重要的是，凝胶具有快速自愈合的特性，只要将切割后的凝胶段挤压在一起，凝胶就能在切割后立即愈合。毫无疑问，我们的研究结果为基于 LMMG 的分子凝胶的流变性能确立了一个基准。傅立叶变换红外光谱、1H NMR 和 XRD 研究表明，分子间氢键和 π-π 堆积是促进体系凝胶化和凝胶剂分子自组装的两个主要驱动力。
• Self-assembling of Cholesterol-appended Benzothiadiazole Fluorescent Dyes
  作者：Tsutomu Ishi-i、Nozomi Nakamura、Naoyuki Esaki、Shogo Amemori

  DOI：10.1246/cl.2008.1166

  日期：2008.11.5

  Cholesterol-appended benzothiadiazole fluorescent dyes were self-assembled to form aggregates through van der Waals interactions among the cholesterol moieties, hydrogen-bonding interactions among the carbamate moieties, and π-stacking interactions among the benzothiadiazole moieties.

  胆固醇附加的苯并噻二唑荧光染料通过胆固醇基团之间的范德华相互作用、氨基甲酸基团之间的氢键相互作用以及苯并噻二唑基团之间的π-堆叠相互作用自组装形成聚集体。
• New triangular steroid-based A(LS)₃ type gelators for selective fluoride sensing application
  作者：Manisha Devi、Abhimanew Dhir、Pooja Pooja、Chullikkattil P. Pradeep

  DOI：10.1039/c4ra03070b

  日期：——

  A new series of triangular steroid-based A(LS)₃ type gelators has been developed which exhibited selective fluoride sensing abilities. The gelation, self-assembly and anion sensing properties of these gelators could be controlled by systematically altering their molecular structures.

  一种新系列的三角形类固醇基A(LS)₃型凝胶剂已经开发出来，展现出选择性的氟离子感应能力。这些凝胶剂的凝胶化、自组装和阴离子感应性质可以通过系统地改变它们的分子结构来控制。
• Synthesis of novel cholesterol-based cationic lipids for gene delivery
  作者：Bieong-Kil Kim、Kyung-Oh Doh、Joo Hyeung Nam、Hyungu Kang、Jong-Gu Park、Ik-Jae Moon、Young-Bae Seu

  DOI：10.1016/j.bmcl.2009.04.036

  日期：2009.6

  The new cholesterol-based cationic lipids B, C, and D with an ether linked spacer were synthesized by using aminopropyl chain extension with acrylonitrile. The cholesterol-based cationic lipid A with carbamoyl linkage were also synthesized in order to compare the difference in transfection efficiency of the two linkage types. To this end, GFP expression of these cationic lipids was confirmed respectively. (C) 2009 Elsevier Ltd. All rights reserved.