tert-butyl (4S)-4-<(1R)-1-hydroxy-2-decynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 241478-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: tert-butyl (4S)-4-<(1R)-1-hydroxy-2-decynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-4-[(1R)-1-hydroxydec-2-ynyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 241478-31-9
• 化学式: C₂₀H₃₅NO₄
• 分子量: 353.502
• InChiKey: LDURJHUQKOLULF-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-4-<(1R)-1-hydroxy-2-decynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 甲醇 、 Amberlyst 15 、 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 72.0h， 生成 tert-butyl (1S,2R,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
• 作为产物：
  描述：

  1-壬炔 、 3-反-溴碳-2,2'-二甲基氧酸酯 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到tert-butyl (4S)-4-<(1R)-1-hydroxy-2-decynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase

  摘要：

  Short-chain sphinganine analogues 8, 9, 18, and 19 as well as 3-fluoro-sphingosine analogues 25 and 26 were synthesized. Their potential as sphingosine kinase inhibitors was investigated, in combination with previously synthesized sphingosine and fluorinated sphinganine analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00554-5

文献信息

• De Jonghe, Steven; Van Overmeire, Ilse; Van Calenbergh, Serge, European Journal of Organic Chemistry, 2000, # 18, p. 3177 - 3183
  作者：De Jonghe, Steven、Van Overmeire, Ilse、Van Calenbergh, Serge、Hendrix, Chris、Busson, Roger、De Keukeleire, Denis、Herdewijn, Piet

  DOI：——

  日期：——
• 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.
• Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase
  作者：Steven De Jonghe、Ilse Van Overmeire、Samantha Poulton、Chris Hendrix、Roger Busson、Serge Van Calenbergh、Denis De Keukeleire、Sarah Spiegel、Piet Herdewijn

  DOI：10.1016/s0960-894x(99)00554-5

  日期：1999.11

  Short-chain sphinganine analogues 8, 9, 18, and 19 as well as 3-fluoro-sphingosine analogues 25 and 26 were synthesized. Their potential as sphingosine kinase inhibitors was investigated, in combination with previously synthesized sphingosine and fluorinated sphinganine analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.