[(2R)-1-(12-naphthalen-2-yloxydodecoxy)-3-[oxido-[[(1S,2R,6R,7S,8R,9R)-4,4,11,11-tetramethyl-8-phenylmethoxy-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl]oxy]phosphaniumyl]oxypropan-2-yl] hexanoate | 207981-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(2R)-1-(12-naphthalen-2-yloxydodecoxy)-3-[oxido-[[(1S,2R,6R,7S,8R,9R)-4,4,11,11-tetramethyl-8-phenylmethoxy-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl]oxy]phosphaniumyl]oxypropan-2-yl] hexanoate
• CAS: 207981-81-5
• 化学式: C₅₀H₇₃O₁₂P
• 分子量: 897.096
• InChiKey: XHGUISJQUZAMCG-QBLAQZBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  63
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R)-1-(12-naphthalen-2-yloxydodecoxy)-3-[oxido-[[(1S,2R,6R,7S,8R,9R)-4,4,11,11-tetramethyl-8-phenylmethoxy-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl]oxy]phosphaniumyl]oxypropan-2-yl] hexanoate 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 乙二醇 为溶剂， 以67%的产率得到[(2R)-1-[[(3aR,4S,5R,6S,7S,7aR)-6,7-dihydroxy-2,2-dimethyl-5-phenylmethoxy-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl]oxyphosphonoyloxy]-3-(12-naphthalen-2-yloxydodecoxy)propan-2-yl] hexanoate
  参考文献：
  名称：

  Synthesis of fluorescent phosphatidylinositols using a novel inositol H-phosphonate

  摘要：

  Coupling of 1,2-diradyl-sn-glycerol 5 with the novel inositol H-phosphonate derivative, 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate (3), gave fluorescent analogs of phosphatidylinositol (PtdIns, 1) and PtdIns(4,5)-bisphosphate (PtdIns(4,5)P-2, 2). Unlike the corresponding phosphoramidate, 3 was stable at -20 degrees C for several months, making it a useful intermediate for the synthesis of myo-inositol phospholipids. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00418-3
• 作为产物：
  描述：

  1,12-二溴十二烷 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 二正丁基氧化锡 、 potassium carbonate 、 对甲苯磺酸 、 cesium fluoride 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成 [(2R)-1-(12-naphthalen-2-yloxydodecoxy)-3-[oxido-[[(1S,2R,6R,7S,8R,9R)-4,4,11,11-tetramethyl-8-phenylmethoxy-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-yl]oxy]phosphaniumyl]oxypropan-2-yl] hexanoate
  参考文献：
  名称：

  Synthesis of fluorescent phosphatidylinositols using a novel inositol H-phosphonate

  摘要：

  Coupling of 1,2-diradyl-sn-glycerol 5 with the novel inositol H-phosphonate derivative, 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate (3), gave fluorescent analogs of phosphatidylinositol (PtdIns, 1) and PtdIns(4,5)-bisphosphate (PtdIns(4,5)P-2, 2). Unlike the corresponding phosphoramidate, 3 was stable at -20 degrees C for several months, making it a useful intermediate for the synthesis of myo-inositol phospholipids. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00418-3

文献信息

• Synthesis of fluorescent phosphatidylinositols using a novel inositol H-phosphonate
  作者：Lawrence W Leung、Catherine Vilchèze、Robert Bittman

  DOI：10.1016/s0040-4039(98)00418-3

  日期：1998.5

  Coupling of 1,2-diradyl-sn-glycerol 5 with the novel inositol H-phosphonate derivative, 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate (3), gave fluorescent analogs of phosphatidylinositol (PtdIns, 1) and PtdIns(4,5)-bisphosphate (PtdIns(4,5)P-2, 2). Unlike the corresponding phosphoramidate, 3 was stable at -20 degrees C for several months, making it a useful intermediate for the synthesis of myo-inositol phospholipids. (C) 1998 Elsevier Science Ltd. All rights reserved.