2-氨基-3-(十六烷氧基)-1-丙醇 | 136770-76-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氨基-3-(十六烷氧基)-1-丙醇
• 英文名称: 1-O-hexadecyl-2-amino-2-deoxy-sn-glycerol
• 英文别名: (S)-2-amino-3-(hexadecyloxy)propan-1-ol；1-O-hexadecyl-2-amino-propane-3-ol；1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol；(2S)-2-amino-3-hexadecoxypropan-1-ol
• CAS: 136770-76-8
• 化学式: C₁₉H₄₁NO₂
• 分子量: 315.54
• InChiKey: BAJLFGHOMLHSCH-IBGZPJMESA-N

物化性质

• 沸点：
  439.1±25.0 °C(Predicted)
• 密度：
  0.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-3-(十六烷氧基)-1-丙醇 在 吡啶 作用下， 反应 4.0h， 生成 N-((R)-1-acetyl-3-(1-hexadecyloxy)propan-2-yl)formamide
  参考文献：
  名称：

  Total synthesis of (R)-(−)-actisonitrile via O-alkylation of optically active 4-hydroxymethyloxazolidin-2-one derivative

  摘要：

  The enantioselective synthesis of (R)-(-)-actisonitrile 1 has been achieved via O-alkylation of (4R,alpha S)-4-hydroxymethyl-3-(alpha-methylbenzyl)oxazolidin-2-one (alpha S)-4 with 1-iodohexadecane in the presence of CsOH in DMF. Under these reaction conditions, the O-alkylation was much faster than the intramolecular acyl transfer of (alpha S)-4. (C)2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.002
• 作为产物：
  描述：

  对甲苯磺酸十六烷基酯 在 甲烷磺酸 、 lithium hydroxide monohydrate 、 cesiumhydroxide monohydrate 、 苯甲醚 作用下， 以 硝基甲烷 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 2-氨基-3-(十六烷氧基)-1-丙醇
  参考文献：
  名称：

  Total synthesis of (R)-(−)-actisonitrile via O-alkylation of optically active 4-hydroxymethyloxazolidin-2-one derivative

  摘要：

  The enantioselective synthesis of (R)-(-)-actisonitrile 1 has been achieved via O-alkylation of (4R,alpha S)-4-hydroxymethyl-3-(alpha-methylbenzyl)oxazolidin-2-one (alpha S)-4 with 1-iodohexadecane in the presence of CsOH in DMF. Under these reaction conditions, the O-alkylation was much faster than the intramolecular acyl transfer of (alpha S)-4. (C)2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.002

文献信息

• Synthesis of [32P]labelled 1-O-alkyl-2-desoxy-2-amino-sn′-glycero-3-phosphocholines
  作者：H. P. Deigner、B. Fyrnys

  DOI：10.1002/jlcr.2580340212

  日期：1994.2

  The syntheses of N-substituted 1-O-alkyl-2-desoxy-2-amino-sn-glycero-3-[32P]phosphocholines were performed in four steps starting from [32P] POCl3 and the corresponding 1-O-alkyl-2-amino-propane-3-ols in 5-7% total yield.

  以[32P] POCl3 和相应的 1-O-烷基-2-氨基-3-丙醇为起点，分四个步骤合成了 N-取代的 1-O-烷基-2-脱氧-2-氨基-sn-甘油-3-[32P]磷脂酰胆碱，总产率为 5-7%。
• Synthesis of enantiomerically pure, sn-1 modified sn-2-deoxy-2-amido-glycero-3-phospholipids
  作者：Markus Bartel、Bernd Rattay、Peter Nuhn

  DOI：10.1016/s0009-3084(00)00156-0

  日期：2000.9

  The synthesis of two types of enantiomerically pure sn-2-deoxy-2-amido-glycero-phospholipids differing in the connection of the alkyl chain at the sn-1-position is described. Both types of lipids were prepared from L-serine-methylester as the chiral starting material. (C) 2000 Published by Elsevier Science Ireland Ltd.
• A Convenient Synthesis of 1-Ether-2-acylamido-2-deoxy-<i>sn</i>-glycerophospholipids
  作者：M. L. García、J. Pascual、G. González、A. Palomer、M. Cabré、J. A. Andreu、D. Mauleón、G. Carganico

  DOI：10.1080/00397919308011175

  日期：1993.12

  A series of 1-ether-sn-2-acylamidoglycerophospholipids, bearing different polar heads in sn-3-position such as phosphoglycol, -serine, -ethanolamine or -choline, have been prepared. Except for the choline derivative which was synthesized from a beta-carbamate alcohol derivative, the remaining compounds were obtained from beta-amidoalcohols.
• Total synthesis of (R)-(−)-actisonitrile via O-alkylation of optically active 4-hydroxymethyloxazolidin-2-one derivative
  作者：Shigeo Sugiyama、Akihiro Ishida、Moeko Tsuchida、Keitaro Ishii

  DOI：10.1016/j.tetasy.2011.11.002

  日期：2011.11

  The enantioselective synthesis of (R)-(-)-actisonitrile 1 has been achieved via O-alkylation of (4R,alpha S)-4-hydroxymethyl-3-(alpha-methylbenzyl)oxazolidin-2-one (alpha S)-4 with 1-iodohexadecane in the presence of CsOH in DMF. Under these reaction conditions, the O-alkylation was much faster than the intramolecular acyl transfer of (alpha S)-4. (C)2011 Elsevier Ltd. All rights reserved.