(3S,4S)-4-methyl-5-hexen-3-yl azide | 147227-14-3

• 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: (3S,4S)-4-methyl-5-hexen-3-yl azide
• 英文别名: (3S,4S)-4-azido-3-methylhex-1-ene
• CAS: 147227-14-3
• 化学式: C₇H₁₃N₃
• 分子量: 139.2
• InChiKey: ONBQOAILUYVIDR-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-methyl-5-hexen-3-yl azide 在 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 (2R,3S)-3-azido-2-methylpentanoic acid
  参考文献：
  名称：

  Asymmetric syntheses of 3-amino-2-methylpentanoic acids. Configurations of the β-amino acid in majusculamide C, 57-normajusculamide C and dolastatins 11 and 12

  摘要：

  The first synthesis of 3-amino-2-methylpentanoic acids is reported. Comparison of the synthetic 2R,3R and 2L,3S acids with 3-amino-2-methylpentanoic acid obtained by degradation of the antifungal depsipeptide majusculamide C indicates that majusculamide C, 57-normajusculamide C, and the antitumor agents dolastatins 11 and 12 have the 2S,3R configurations at the chiral centers in their beta-amino acid component.

  DOI：

  10.1016/s0957-4166(00)86016-4
• 作为产物：
  描述：

  (3R,4S)-4-methyl-5-hexen-3-yl mesylate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (3S,4S)-4-methyl-5-hexen-3-yl azide
  参考文献：
  名称：

  Asymmetric syntheses of 3-amino-2-methylpentanoic acids. Configurations of the β-amino acid in majusculamide C, 57-normajusculamide C and dolastatins 11 and 12

  摘要：

  The first synthesis of 3-amino-2-methylpentanoic acids is reported. Comparison of the synthetic 2R,3R and 2L,3S acids with 3-amino-2-methylpentanoic acid obtained by degradation of the antifungal depsipeptide majusculamide C indicates that majusculamide C, 57-normajusculamide C, and the antitumor agents dolastatins 11 and 12 have the 2S,3R configurations at the chiral centers in their beta-amino acid component.

  DOI：

  10.1016/s0957-4166(00)86016-4

文献信息

• Asymmetric syntheses of 3-amino-2-methylpentanoic acids. Configurations of the β-amino acid in majusculamide C, 57-normajusculamide C and dolastatins 11 and 12
  作者：Robert B. Bates、Sanjeev Gangwar

  DOI：10.1016/s0957-4166(00)86016-4

  日期：1993.1

  The first synthesis of 3-amino-2-methylpentanoic acids is reported. Comparison of the synthetic 2R,3R and 2L,3S acids with 3-amino-2-methylpentanoic acid obtained by degradation of the antifungal depsipeptide majusculamide C indicates that majusculamide C, 57-normajusculamide C, and the antitumor agents dolastatins 11 and 12 have the 2S,3R configurations at the chiral centers in their beta-amino acid component.