N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)-8-methyl-6-(2-methylpropyl)non-3-enyl]undecanamide | 1142922-76-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)-8-methyl-6-(2-methylpropyl)non-3-enyl]undecanamide
• 英文别名: N-[(E,2S,3R)-1,3-dihydroxy-9-methyl-7-(2-methylpropyl)dec-4-en-2-yl]undecanamide
• CAS: 1142922-76-6
• 化学式: C₂₆H₅₁NO₃
• 分子量: 425.696
• InChiKey: HHTJIRGUQMQUSP-YKRDXMSESA-N

物化性质

• 沸点：
  583.6±50.0 °C(predicted)
• 密度：
  0.937±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  十一烷酰氯 、 在 magnesium oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以39 mg的产率得到N-[(3E)(1S,2R)-2-hydroxy-1-(hydroxymethyl)-8-methyl-6-(2-methylpropyl)non-3-enyl]undecanamide
  参考文献：
  名称：

  Ceramides: Branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency

  摘要：

  The synthesis of a small number of ceramide analogues containing a combination of linear and highly branched alkyl chains on either the D-sphingosine or the N-acyl core of the molecule is reported. Regardless of location, the presence of the branched chain improves potency relative to the positive control, C2 ceramide; however, the most potent compound (4) has the branched side chain as part of the D-sphingosine core. The induction of apoptosis by 4 in terms of Annexin V binding and DiOC(6) labeling was superior to that achieved with C2 ceramide. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.005

文献信息

• Ceramides: Branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency
  作者：Ji-Hye Kang、Himanshu Garg、Dina M. Sigano、Nicholas Francella、Robert Blumenthal、Victor E. Marquez

  DOI：10.1016/j.bmc.2009.01.005

  日期：2009.2

  The synthesis of a small number of ceramide analogues containing a combination of linear and highly branched alkyl chains on either the D-sphingosine or the N-acyl core of the molecule is reported. Regardless of location, the presence of the branched chain improves potency relative to the positive control, C2 ceramide; however, the most potent compound (4) has the branched side chain as part of the D-sphingosine core. The induction of apoptosis by 4 in terms of Annexin V binding and DiOC(6) labeling was superior to that achieved with C2 ceramide. (c) 2009 Elsevier Ltd. All rights reserved.