rac-1,2-di-O-octadecyl-3-O-(4-toluenesulfonyl)glycerol | 152980-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-1,2-di-O-octadecyl-3-O-(4-toluenesulfonyl)glycerol
• 英文别名: 2,3-dioctadecoxypropyl 4-methylbenzenesulfonate
• CAS: 152980-94-4
• 化学式: C₄₆H₈₆O₅S
• 分子量: 751.252
• InChiKey: DZBNMDZYAINNTN-UHFFFAOYSA-N

物化性质

• 沸点：
  760.1±55.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  19
• 重原子数：
  52
• 可旋转键数：
  41
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-1,2-di-O-octadecyl-3-O-(4-toluenesulfonyl)glycerol 在 lithium bromide 作用下， 以 丁酮 为溶剂， 反应 5.0h， 以89.7%的产率得到rac-1-bromo-1-deoxy-2,3-di-O-octadecylglycerol
  参考文献：
  名称：

  Konstantinova, I. D.; Ushakova, I. P.; Serebrennikova, G. A., Russian Journal of Bioorganic Chemistry, 1993, vol. 19, # 8, p. 500 - 503

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-Dioctadecyl-3-benzyl-sn-glycerin 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 10.0h， 生成 rac-1,2-di-O-octadecyl-3-O-(4-toluenesulfonyl)glycerol
  参考文献：
  名称：

  Synthesis and Photoswitchable Complexation/Extraction Properties of Lipophilic Azabis(benzo-15-crown-5) Ionophores for Alkali Metal Cations

  摘要：

  Novel lipophilic derivatives of azobis(benzo-15-crown-5) (1b, 1c) were synthesized and their photoisomerization, complexation and extraction properties for alkali metal cations were investigated. Upon UV light irradiation, the photostationary state of the trans and cis isomers was reached and, with both 1b and 1c, the extractabilities of Rb+ and Cs+ increased due to the formation of 1:1 sandwich-type complexes by the cis isomers. On the other hand, the extractability of K+ decreased, possibly because the 2:1 complexes formed by the trans isomers are more stable and/or lipophilic than the complexes of the cis isomers.

  DOI：

  10.3987/com-97-s(n)87

文献信息

• Synthesis of Nucleosides with 2′-Fixed Lipid Anchors and Their Behavior in Phospholipid Membranes
  作者：Oliver Kaczmarek、Nicolai Brodersen、Andreas Bunge、Ludwig Löser、Daniel Huster、Andreas Herrmann、Anna Arbuzova、Jürgen Liebscher

  DOI：10.1002/ejoc.200701064

  日期：2008.4

  Various new nucleosides bearing one or two lipophilic groups at the 2′-position have been synthesized. The lipophilic substituents were attached to a 2′-hydroxy, 2′-amino, or 2′-thio function. These lipophilic nucleosides anchor in large unilamellar POPC vesicles serving as phospholipid membrane models. The insertion of these molecules into the membranes was investigated by NMR techniques. For comparison

  已经合成了各种在 2' 位带有一个或两个亲脂基团的新核苷。亲脂性取代基连接到 2'-羟基、2'-氨基或 2'-硫代官能团。这些亲脂性核苷锚定在用作磷脂膜模型的大型单层 POPC 囊泡中。通过核磁共振技术研究了这些分子插入到膜中的情况。为了进行比较，还研究了在 2'-、3'-或 5'-位置具有两个或三个亲脂基团的核苷。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）
• Synthesis of alkyl glycerolipids with various cationic groups linked directly to the glycerol backbone
  作者：M. A. Maslov、E. V. Sycheva、N. G. Morozova、G. A. Serebrennikova

  DOI：10.1007/bf02495307

  日期：1999.7

  A number of positively charged lipids containing pyridinium, N-methylmorpholinium, N-methylimidazolinium, 4-N,N-dimethylaminopyridinium, and 4-N,N-dimethylcyclohexylammonium groups linked directly to the C(3) atom of 1,2-di-O-alkylglycerols with Br-, MsO-, and TsO- anions as counterions were synthesized.