(R)-1,2-O-isopropylidene-3-O-(4-methoxyphenyl)glycerol | 130998-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-1,2-O-isopropylidene-3-O-(4-methoxyphenyl)glycerol
• 英文别名: (4S)-4-[(4-methoxyphenoxy)methyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 130998-32-2
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: AIEFXBWJQHZGJZ-LBPRGKRZSA-N

物化性质

• 沸点：
  329.2±22.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1,2-O-isopropylidene-3-O-(4-methoxyphenyl)glycerol 在 吡啶 、 硫酸 、 potassium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成 [(2R)-2-acetyloxy-3-(4-methoxyphenoxy)propyl] acetate
  参考文献：
  名称：

  Practical Route to Both (S)- and (R)-Enantiomers of O-(4-Methoxyphenyl)glycidol Using (S)-1,2-O-Isopropylideneglycerol as a Common Precursor

  摘要：

  DOI：

  10.3987/com-90-5476
• 作为产物：
  描述：

  (S)-(+)-1,2-异亚丙基甘油 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.33h， 生成 (R)-1,2-O-isopropylidene-3-O-(4-methoxyphenyl)glycerol
  参考文献：
  名称：

  Practical Route to Both (S)- and (R)-Enantiomers of O-(4-Methoxyphenyl)glycidol Using (S)-1,2-O-Isopropylideneglycerol as a Common Precursor

  摘要：

  DOI：

  10.3987/com-90-5476

文献信息

• GLYCERO-COMPOUND HAVING TRIPLE BOND AND MEMBRANE MATERIAL CONTAINING THE SAME
  申请人：BABA Teruhiko

  公开号：US20070105823A1

  公开（公告）日：2007-05-10

  The present invention provides a chemically stable and novel glycero-compound having one or two triple bonds, one molecule of a glycerol and one or two molecules of a fatty alcohol having a triple bond being linked through an ether bond, an organic group being linked to residual hydroxyl groups of the glycerol, which can be used as a membrane material for forming a vesicle membrane due to its high intermolecular cohesive force, and also provides a membrane forming material containing the same. The glycero-compound has a triple bond represented by the following general formula (1): wherein n and m each represents a number of 1 to 17 and the total (n+m) is a number of 4 to 18, n and m may be the same or different, and R represents a hydrogen atom, a metal atom, a phosphoric acid group, or an organic group which may be linked through a phosphoric acid group.

  本发明提供了一种化学稳定且新颖的甘油化合物，其中含有一个或两个三键，一个甘油分子和一个或两个含有三键的脂肪醇分子通过醚键连接，有机基与甘油的残余羟基连接，由于其高分子间内聚力可用作形成囊泡膜的膜材料，还提供了含有相同物质的膜形成材料。该甘油化合物具有以下一般式（1）所代表的三键：其中n和m分别表示1到17之间的数字，总数（n+m）为4到18之间的数字，n和m可以相同也可以不同，R表示氢原子、金属原子、磷酸基或可以通过磷酸基连接的有机基。
• Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative
  作者：Masazumi Iwashita、Kumiko Makide、Taro Nonomura、Yoshimasa Misumi、Yuko Otani、Mayuko Ishida、Ryo Taguchi、Masafumi Tsujimoto、Junken Aoki、Hiroyuki Arai、Tomohiko Ohwada

  DOI：10.1021/jm900598m

  日期：2009.10.8

  In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs.
• Structure–Activity Relationships of Lysophosphatidylserine Analogs as Agonists of G-Protein-Coupled Receptors GPR34, P2Y10, and GPR174
  作者：Masaya Ikubo、Asuka Inoue、Sho Nakamura、Sejin Jung、Misa Sayama、Yuko Otani、Akiharu Uwamizu、Keisuke Suzuki、Takayuki Kishi、Akira Shuto、Jun Ishiguro、Michiyo Okudaira、Kuniyuki Kano、Kumiko Makide、Junken Aoki、Tomohiko Ohwada

  DOI：10.1021/jm5020082

  日期：2015.5.28

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, we examined the structure-attivity relationships of a series of synthetic LysoPS analogues toward these recently deorphanized LysoPS,receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and L-Serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysolPS, 1), we optimized the structure of each module and the ester linkage. Accordingly, we identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174.
• Synthesis of phospholipids containing perfluorooctyl group and their interfacial properties
  作者：Toshiyuki Takagi、Katsuki Takai、Teruhiko Baba、Toshiyuki Kanamori

  DOI：10.1016/j.jfluchem.2006.10.020

  日期：2007.2

  Highly fluorinated single-chained and/or double-chained phospholipids containing the perfluorooctyl group as the terminal segment of hydrophobic chains and a phosphocholine moiety as the hydrophilic headgroup were synthesized in order to investigate the effect of fluorinated segments on the stability of phospholipid monolayers formed at the air-water interface. Judging from the equilibrium spreading pressures (pi(e)s) Of their monolayers at the air-water interface, all of the fluorinated phospholipids formed more stable monolayers than the corresponding non-fluorinated counterparts. In addition, the fluorinated double-chained phosphatidylcholine containing C-C triple bond (monoyne group) formed stable and fluid vesicle membranes in water, although the single-chained phospholipids did not form vesicle membranes but micellar solutions under the present conditions. (c) 2006 Elsevier B.V. All rights reserved.
• TAKANO, SEIICHI;MORIYA, MINORU;SUZUKI, MAHITO;IWABUCHI, YOAHIHARU;SUGIHAR+, HETEROCYCLES, 31,(1990) N, C. 1555-1563
  作者：TAKANO, SEIICHI、MORIYA, MINORU、SUZUKI, MAHITO、IWABUCHI, YOAHIHARU、SUGIHAR+

  DOI：——

  日期：——