(2RS,4Z)-1-azido-4-decen-2-ol | 157423-42-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2RS,4Z)-1-azido-4-decen-2-ol
• 英文别名: (Z)-1-azidodec-4-en-2-ol
• CAS: 157423-42-2
• 化学式: C₁₀H₁₉N₃O
• 分子量: 197.28
• InChiKey: ZJEJINDELHVVPA-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2RS,4Z)-1-azido-4-decen-2-ol 在 钯 盐酸 、 甲醇 、 氢氧化钾 、 高氯酸 、 氢气 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (2S^*,4R^*,5R^*)-2,4,5-trihydroxy-1-decylamine hydrochloride
  参考文献：
  名称：

  Absolute configuration of main chain of AAL-toxins.

  摘要：

  AAL-toxins TA(1) 1 and TA(2) 2, host-specific toxins produced by Alternaria alternata, were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-aminobutan-1-3-diol, which were further converted to (R)-MTPA esters. These esters were correlated with synthesis samples by comparison of their 500 MHz H-1-NMR spectra. The remaining stereocenters were determined by the comparison of H-1-NMR spectra of 6a and 7 derived from 1 and 2 with those of synthetic model compounds. These data conclude that AAL-toxins possess 2S, 4S, 5R, 11S, 13S, 14R and 15R configurations.

  DOI：

  10.1016/s0040-4020(01)89343-1
• 作为产物：
  描述：

  (2RS,4Z)-1-tosyloxy-4-decen-2-ol 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到(2RS,4Z)-1-azido-4-decen-2-ol
  参考文献：
  名称：

  AAL毒素的C（1）C（5）片段的绝对配置：构象刚性无环氨基三醇部分

  摘要：

  AAL-毒素降解1宿主特异性植物毒素和模型aminotriol的合成图7a - 7D使我们能够确定C的绝对构型（1）C（5）片段作为2小号，4小号和5 - [R 。还讨论了该无环片段的异常刚性构象。

  DOI：

  10.1016/0040-4039(94)88029-8

文献信息

• Absolute configuration of C(1)C(5) fragment of AAL-toxin: Conformationally rigid acyclic aminotriol moiety
  作者：Hideaki Oikawa、Isamu Matsuda、Akitami Ichihara、Keisuke Kohmoto

  DOI：10.1016/0040-4039(94)88029-8

  日期：1994.2

  Degradation of AAL-toxin 1 a host-specific phytotoxin and synthesis of model aminotriol 7a - 7d allowed us to determine the absolute configuration of C(1)C(5) fragment as 2S, 4S and 5R. Unusually rigid conformation of this acyclic fragment was also discussed.

  AAL-毒素降解1宿主特异性植物毒素和模型aminotriol的合成图7a - 7D使我们能够确定C的绝对构型（1）C（5）片段作为2小号，4小号和5 - [R 。还讨论了该无环片段的异常刚性构象。
• Absolute configuration of main chain of AAL-toxins.
  作者：Hideaki Oikawa、Isamu Matsuda、Takashi Kagawa、Akitami Ichihara、Keisuke Kohmoto

  DOI：10.1016/s0040-4020(01)89343-1

  日期：1994.1

  AAL-toxins TA(1) 1 and TA(2) 2, host-specific toxins produced by Alternaria alternata, were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-aminobutan-1-3-diol, which were further converted to (R)-MTPA esters. These esters were correlated with synthesis samples by comparison of their 500 MHz H-1-NMR spectra. The remaining stereocenters were determined by the comparison of H-1-NMR spectra of 6a and 7 derived from 1 and 2 with those of synthetic model compounds. These data conclude that AAL-toxins possess 2S, 4S, 5R, 11S, 13S, 14R and 15R configurations.