(S)-4-azide-nonadec-1-en | 891171-65-6

• 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: (S)-4-azide-nonadec-1-en
• CAS: 891171-65-6
• 化学式: C₁₉H₃₇N₃
• 分子量: 307.523
• InChiKey: RAOJDBVJKPKOFC-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  22.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  48.76
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (S)-4-azide-nonadec-1-en 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 (2Z,5S)-hydroxyicos-2-enoic acid δ-lactam
  参考文献：
  名称：

  Antiparasite and antimycobacterial activity of passifloricin analogues

  摘要：

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.02.017
• 作为产物：
  描述：

  (R)-4-p-toluenesulphinate-nonadec-1-en 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (S)-4-azide-nonadec-1-en
  参考文献：
  名称：

  Antiparasite and antimycobacterial activity of passifloricin analogues

  摘要：

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/j.tet.2006.02.017