tert-butyl (1S,2S,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate | 241478-41-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (1S,2S,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate
• 英文别名: tert-butyl N-[(E,2S,3S)-1,3-dihydroxydodec-4-en-2-yl]carbamate
• CAS: 241478-41-1
• 化学式: C₁₇H₃₃NO₄
• 分子量: 315.453
• InChiKey: QEJUXXUIIOSOLZ-NOQIOLJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2S,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 (2S,3S,4E)-2-amino-4-dodecene-1,3-diol
  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：

  tert-butyl (1S,2S)-2-hydroxy-1-(hydroxymethyl)-3-undecynylcarbamate 在 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 24.0h， 以59%的产率得到tert-butyl (1S,2S,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate
  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

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.