(2S,3R,4E)-2-amino-5-phenyl-4-pentene-1,3-diol | 241478-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2S,3R,4E)-2-amino-5-phenyl-4-pentene-1,3-diol
• 英文别名: (E,2S,3R)-2-amino-5-phenylpent-4-ene-1,3-diol
• CAS: 241478-48-8
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: KAOAFWORMXLRDR-FQLSZKSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  己酸 、 (2S,3R,4E)-2-amino-5-phenyl-4-pentene-1,3-diol 在 1-羟基苯并三唑 、 达卡巴嗪 作用下， 以 二氯甲烷 为溶剂， 生成 Hexanoic acid ((E)-(1S,2R)-2-hydroxy-1-hydroxymethyl-4-phenyl-but-3-enyl)-amide
  参考文献：
  名称：

  Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons

  摘要：

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.

  DOI：

  10.1021/jm990091e
• 作为产物：
  描述：

  (E)-2-penten-4-yn-1-ol 在 哌啶 、 titanium(IV) isopropylate 、 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 D-(-)-酒石酸二乙酯 、 水 、 三乙胺 、 红铝 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 63.0h， 生成 (2S,3R,4E)-2-amino-5-phenyl-4-pentene-1,3-diol
  参考文献：
  名称：

  对鞘二烯胺和芳香族神经酰胺类似物的对映选择性合成‡

  摘要：

  已经开发了一种新的合成鞘氨醇碱基的方法。该策略基于手性炔属氨基甲酸酯的Sonogashira偶联，可以从2,3-环氧--4-戊炔-1-醇以对映体富集的形式制备，可通过Sharpless不对称环氧化轻松获得。已经合成了几种N -Boc-鞘氨醇二烯和芳香族神经酰胺类似物。

  DOI：

  10.1021/ol202064j

文献信息

• Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons
  作者：Ilse Van Overmeire、Swetlana A. Boldin、Filip Dumont、Serge Van Calenbergh、Guido Slegers、Denis De Keukeleire、Anthony H. Futerman、Piet Herdewijn

  DOI：10.1021/jm990091e

  日期：1999.7.1

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.
• Enantioselective Synthesis of Sphingadienines and Aromatic Ceramide Analogs
  作者：María Moreno、Caterina Murruzzu、Antoni Riera

  DOI：10.1021/ol202064j

  日期：2011.10.7

  A new approach to the synthesis of sphingoid bases has been developed. The strategy is based on Sonogashira coupling of a chiral acetylenic carbamate that can be prepared in enantiomerically enriched form from 2,3-epoxy-4-pentyn-1-ol, which is readily accessible by Sharpless asymmetric epoxidation. Several N-Boc-sphingadienines and aromatic ceramide analogs have been synthesized.

  已经开发了一种新的合成鞘氨醇碱基的方法。该策略基于手性炔属氨基甲酸酯的Sonogashira偶联，可以从2,3-环氧--4-戊炔-1-醇以对映体富集的形式制备，可通过Sharpless不对称环氧化轻松获得。已经合成了几种N -Boc-鞘氨醇二烯和芳香族神经酰胺类似物。