Heptansaeureester v. Propin-(2)-ol-(1) | 26771-53-9

• 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: Heptansaeureester v. Propin-(2)-ol-(1)
• 英文别名: Prop-2-ynyl heptanoate
• CAS: 26771-53-9
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: MXVLZVAZHQSIHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  60-62 °C(Press: 3 Torr)
• 密度：
  0.9163 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  Heptansaeureester v. Propin-(2)-ol-(1) 、 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl azide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.23h， 以97.7%的产率得到(1-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-1H-1,2,3-triazol-4-yl)methyl heptanoate
  参考文献：
  名称：

  Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.10.033
• 作为产物：
  描述：

  庚酸 、 3-溴丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Heptansaeureester v. Propin-(2)-ol-(1)
  参考文献：
  名称：

  Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.10.033

文献信息

• 919. Physical properties and chemical constitution. Part XXIX. Acetylenic compounds
  作者：Roman Grzeskowiak、George H. Jeffery、Arthur I. Vogel

  DOI：10.1039/jr9600004719

  日期：——
• MAXSUMOV, A. G.;EHRGASHEV, M. S., UZB. XIM. ZH., 1984, N 2, 26-29
  作者：MAXSUMOV, A. G.、EHRGASHEV, M. S.

  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.