Palmitic acid propargylic ester | 6900-04-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Palmitic acid propargylic ester
• 英文别名: prop-2-ynyl palmitate；propargyl palmitate；Propargylhexadecanoat；Prop-2-yn-1-yl hexadecanoate；prop-2-ynyl hexadecanoate
• CAS: 6900-04-5
• 化学式: C₁₉H₃₄O₂
• 分子量: 294.478
• InChiKey: OCQCAVLTZIMSFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  384.0±15.0 °C(Predicted)
• 密度：
  0.893±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Palmitic acid propargylic ester 在 copper(ll) sulfate pentahydrate 、 氢气 、 sodium ascorbate 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.67h， 生成 [1-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]triazol-4-yl]methyl hexadecanoate
  参考文献：
  名称：

  Disclosing the distinct interfacial behaviors of structurally and configurationally diverse triazologlycolipids

  摘要：

  1- or 6-Triazologluco- and galactolipid derivatives bearing a lipid chain length of 16 carbons were efficiently constructed via click chemistry. The differentiation in their surface pressure-molecular area (pi-A) isotherms first implies that these structurally and configurationally diverse amphiphiles adopt different distribution manner at air-water interfaces. The Langmuir-Blodgett (LB) films of the synthesized glycoconjugates on mica surface were subsequently prepared and visualized via atomic force microscopy (AFM), which exhibited diverse topographies and possess different contact angles with water. These data further suggest that the structural variation as well as epimeric identity of triazologlycolipids may result in their distinct interfacial behaviors at the air-solid interface. Furthermore, the addition of increasing amounts of 1-triazologalactolipid 2 to poly-diacetylene (PDA) was determined to impact the pi-A isotherm of the latter, prompting us to further fabricate new colorimetrically detectable mixed-type vesicles containing triazologlycolipids for biochemical studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.038
• 作为产物：
  描述：

  2-丙炔-1-醇 、 棕榈酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以57%的产率得到Palmitic acid propargylic ester
  参考文献：
  名称：

  通过开环聚合和点击化学结合制备的两亲嵌段接枝共聚物聚（乙二醇）-b-（聚碳酸酯-g-棕榈酸酯）

  摘要：

  两性嵌段接枝共聚物mPEG‐ b ‐P（DTC‐ADTC‐ g‐Pal）是通过以聚（乙二醇）单甲醚（mPEG）为引发剂的碳酸2,2-二甲基三亚甲基酯（DTC）和碳酸2,2-双（叠氮甲基）三亚甲基碳酸酯（ADTC）的开环聚合反应合成的，然后通过棕榈酸炔丙酯和聚合物链上的侧基叠氮基的点击反应。通过将水添加到聚合物的THF溶液中，然后通过透析除去有机溶剂，可以制备两亲嵌段接枝共聚物的稳定胶束溶液。动态光散射测量表明，胶束具有窄的尺寸分布。透射电子显微镜图像显示，胶束呈球形。接枝结构可以增强聚合物链与药物分子的相互作用，提高载药量和包封率。此外，两亲性嵌段接枝共聚物mPEG-b -P（DTC-ADTC- g -Pal ）具有低细胞毒性，并且具有更持久的药物释放行为。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2012年

  DOI：

  10.1002/pola.26051

文献信息

• Synthesis and Evaluation of Novel Oleanolic Acid Derivatives as Potential Antidiabetic Agents
  作者：Liying Zhang、Xiaojian Jia、Jizhe Dong、Dongyin Chen、Jun Liu、Luyong Zhang、Xiaoan Wen

  DOI：10.1111/cbdd.12241

  日期：2014.3

  exhibited moderate‐to‐good inhibitory activities against glycogen phosphorylase. Compound 8g showed the best inhibition with an IC50 value of 5.4 μm. Moreover, most of the derivatives were found to increase the glucose consumption in HepG2 cells in a dose‐dependent manner. The possible binding mode of compound 8g with glycogen phosphorylase was also explored by docking study. 8g was found to have hydrogen

  抗糖尿病药同时抑制肝葡萄糖生成并刺激肝葡萄糖消耗可以更好地控制高血糖症。为了寻找这类药物，设计并合成了一系列在C-3位具有大取代基的齐墩果酸衍生物。使用糖原磷酸化酶和HepG2细胞在体外对所有化合物进行了生物学评估。结果表明，几种衍生物对糖原磷酸化酶表现出中等至良好的抑制活性。化合物8克显示出最好的抑制，其IC 50为5.4μ值米。此外，发现大多数衍生物以剂量依赖的方式增加HepG2细胞的葡萄糖消耗。还通过对接研究探索了化合物8g与糖原磷酸化酶的可能结合方式。发现8g与变构位点的Arg193，Arg310和Arg60具有氢键相互作用。
• Synthesis and antitumor activity of 7-(triazol-1-yl)pyrroloallocolchicine derivatives
  作者：N. S. Sitnikov、A. V. Sintsov、E. S. Shchegravina、A. Prokop、H. G. Schmalz、V. V. Fokin、A. Yu. Fedorov

  DOI：10.1007/s11172-015-1018-z

  日期：2015.6

  The cycloaddition of acetylene derivatives of azido-substituted pyrroloallocolchicines afforded 7-(triazol-1-yl)pyrroloallocolchicines. The synthesized compounds exhibit considerable cytotoxicity and apoptosis-inducing activity against Nalm 6 human leukemia cells.

  叠氮基取代的吡咯并别秋水仙碱的乙炔衍生物环加成得到7-(三唑-1-基)吡咯别别秋水仙碱。合成的化合物对 Nalm 6 人类白血病细胞表现出相当大的细胞毒性和凋亡诱导活性。
• A Convenient Entry to New C-7-Modified Colchicinoids through Azide Alkyne [3+2] Cycloaddition: Application of Ring-Contractive Rearrangements
  作者：Hans-Günther Schmalz、Norman Nicolaus、Jens Reball、Nikolay Sitnikov、Alexey Yu. Fedorov、Janna Velder、Andreas Termath

  DOI：10.3987/com-10-s(e)117

  日期：——

  Reliable procedures for the preparation of azides derived from colchicine (1), allocolchicine (3) and N-acetylcolchinol (4a) were developed. These azides were then employed in Cu-catalyzed Huisgen-Sharpless [3+2] cycloaddition ("click") reactions with alkynes under microwave irradiation. The method developed opens a convenient and efficient access to libraries of new C-7-modified colchicinoids (triazole derivatives). In addition, a plausible mechanistic rationale for the colchicine-allocolchicine rearrangement is suggested.
• Grudinin, A. L.; Koshkina, I. M.; Domnin, I. N., Russian Journal of Organic Chemistry, 1993, vol. 29, # 10, p. 1620 - 1630
  作者：Grudinin, A. L.、Koshkina, I. M.、Domnin, I. N.

  DOI：——

  日期：——
• Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments
  作者：Shao-Xing Song、Hai-Lin Zhang、Chol-Guk Kim、Li Sheng、Xiao-Peng He、Yi-Tao Long、Jia Li、Guo-Rong Chen

  DOI：10.1016/j.tet.2010.10.033

  日期：2010.12

  A series of triazole-linked ester-type glycolipids were efficiently prepared via a two-step sequence involving microwave accelerated 'click' chemistry and debenzylation. All carbon chain length varied O-alkynyl fatty esters used to couple with 1-azido-tetra-O-benzyl-beta-D-glucoside showed excellent tolerance to the microwave-assisted 1,3-dipolar cycloaddition (click reaction), forming the unique cycloadducts in almost quantitative yields of 92.9-99.0% within a quarter. The desired glycolipids were then readily afforded via the successive hydrogenolysis promoted by PdCl2/H-2. Their adsorption competence on gold electrode were evaluated through EIS (electrochemical impedance spectroscopy) measurement and the resulting structure-activity relationship (SAR) was discussed. In addition, the cytotoxicity of this triazolyl glycolipid class on HeLa (cervix cancer) cell line was identified by MTT assay. (C) 2010 Elsevier Ltd. All rights reserved.