Hexadecanoic acid (R)-2-hydroxy-2-(4-nitro-phenoxycarbonyl)-ethyl ester | 786704-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: Hexadecanoic acid (R)-2-hydroxy-2-(4-nitro-phenoxycarbonyl)-ethyl ester
• 英文别名: [(2R)-2-hydroxy-3-(4-nitrophenoxy)-3-oxopropyl] hexadecanoate
• CAS: 786704-18-5
• 化学式: C₂₅H₃₉NO₇
• 分子量: 465.587
• InChiKey: AELHTAIGQCEQRH-HSZRJFAPSA-N

物化性质

• 沸点：
  592.5±50.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  33
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Hexadecanoic acid (R)-2-hydroxy-2-(4-nitro-phenoxycarbonyl)-ethyl ester 在 4-甲基苯磺酸吡啶 sodium tetrahydroborate 作用下， 以 乙二醇二甲醚 、 氯仿 为溶剂， 反应 2.0h， 生成 1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-glycerol
  参考文献：
  名称：

  A new approach to the synthesis of lysophospholipids: preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate

  摘要：

  A new stereospecific synthesis of lysophosphatidic acid and lysophosphatidylcholine is reported. The sequence relies on p-nitrophenyl-D-glycerate as a chiral synthon, including chemoselective reduction of the active ester function without affecting other carboxylic ester groups present in the molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.161
• 作为产物：
  描述：

  p-nitrophenyl 2,3-O-isopropylidene-D-glycerate 在 盐酸 作用下， 以 1,4-二氧六环 、 乙腈 、 苯 为溶剂， 反应 76.0h， 生成 Hexadecanoic acid (R)-2-hydroxy-2-(4-nitro-phenoxycarbonyl)-ethyl ester
  参考文献：
  名称：

  A new approach to the synthesis of lysophospholipids: preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate

  摘要：

  A new stereospecific synthesis of lysophosphatidic acid and lysophosphatidylcholine is reported. The sequence relies on p-nitrophenyl-D-glycerate as a chiral synthon, including chemoselective reduction of the active ester function without affecting other carboxylic ester groups present in the molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.161

文献信息

• A new approach to the synthesis of lysophospholipids: preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate
  作者：Renato Rosseto、Niloufar Bibak、Joseph Hajdu

  DOI：10.1016/j.tetlet.2004.07.161

  日期：2004.9

  A new stereospecific synthesis of lysophosphatidic acid and lysophosphatidylcholine is reported. The sequence relies on p-nitrophenyl-D-glycerate as a chiral synthon, including chemoselective reduction of the active ester function without affecting other carboxylic ester groups present in the molecule. (C) 2004 Elsevier Ltd. All rights reserved.