(1R,4S,13R)-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-trien-9-ol | 89460-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1R,4S,13R)-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-trien-9-ol
• CAS: 89460-90-2
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: NFUPCRDUPMGSTK-OHUAYANFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  、 (1R,4S,13R)-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-trien-9-ol 在 四溴化碳 、 三苯基膦 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 (2S,3R,4R,5R)-2-methyl-6-[2-[2-[2-[(1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-trien-9-yl)oxy]ethoxy]ethoxy]ethoxy]oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis and properties of isocannabinoid and cholesterol derivatized rhamnosurfactants: application to liposomal targeting of keratinocytes and skin

  摘要：

  The usefulness of vesicles to cargo material depends on the design of new ligands able to incorporate easily inside the bilayer and also to direct the vesicles to the targeted site. Therefore, the synthesis of two new rhamnose-bearing surfactants is described. The hydrophobic part consists of cholesterol (in compound 3) and citrylidene phloroglucinol (in compound 6). The ability of these two rhamnolipids to incorporate into a DPPC membrane and to form aggregates is investigated, respectively, by differential scanning calorimetry and by surface tension measurements. Those two new surfactants were incorporated in fluorescent liposomes to study their interactions with keratinocytes and skin sections. Intraliposomal delivery to keratinocytes was observed in both cases, even if the kinetics of delivery were different according to the rhamnosurfactant used. Skin sections were stained by both liposomal formulations, and different interactions between the liposomes and skin cells according to the surfactant used were noted. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.009
• 作为产物：
  描述：

  柠檬醛 在 哌啶 、 乙酸酐 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 (1R,4S,13R)-1,5,5-trimethyl-6,15-dioxatetracyclo[9.3.1.04,13.07,12]pentadeca-7(12),8,10-trien-9-ol
  参考文献：
  名称：

  Total Syntheses of Cannabicyclol, Clusiacyclol A and B, Iso-Eriobrucinol A and B, and Eriobrucinol

  摘要：

  Total syntheses of a series of chromane natural products that contain a cyclobutane ring are described. A unified theme In the strategy employed for all these syntheses Is an oxa-[3 + 3] annulation for constructing the chromane nucleus and a stepwise cationic [2 + 2] cycloaddition for the cyclobutane formation. More Importantly, the two reactions could be rendered in tandem, thereby providing an expeditious approach to this family of natural products.

  DOI：

  10.1021/ol401335u

文献信息

• Carbon-13 nuclear magnetic resonance spectra of cannabichromene, cannabicitran, and cannabicyclol and their analogs
  作者：Vinayak V. Kane、Arnold R. Martin、Jo Ann Peters、Phillip Crews

  DOI：10.1021/jo00184a024

  日期：1984.5