(2S)-2-N-acetylamino-5-methylhex-4-enoic acid

• 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: (2S)-2-N-acetylamino-5-methylhex-4-enoic acid
• 英文别名: (2S)-2-acetamido-5-methylhex-4-enoic acid
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: RKGKDLLDINHZOZ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-N-acetylamino-5-methylhex-4-enoic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 5,5-dimethylproline hydrochloride 、 (S)-2-Amino-5-hydroxy-5-methyl-hexanoic acid; hydrochloride
  参考文献：
  名称：

  A catalytic asymmetric synthesis of 5,5-dimethylproline

  摘要：

  The methyl ester derivative of commercially available N-acetyl-allylglycine readily undergoes cross-metathesis with 2-methylbut-2-ene and ruthenium-alkylidene catalyst to afford the prenylglycine derivative. Acid-catalysed cyclisation then affords 5,5-dimethylproline in near quantitative yield and enantioselectivity. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.05.003
• 作为产物：
  描述：

  (2S)-2-acetamidopent-4-enoic acid 、 异丁烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 50.0 ℃ 、34.47 kPa 条件下， 反应 72.0h， 以74%的产率得到(2S)-2-N-acetylamino-5-methylhex-4-enoic acid
  参考文献：
  名称：

  A catalytic asymmetric synthesis of 5,5-dimethylproline

  摘要：

  The methyl ester derivative of commercially available N-acetyl-allylglycine readily undergoes cross-metathesis with 2-methylbut-2-ene and ruthenium-alkylidene catalyst to afford the prenylglycine derivative. Acid-catalysed cyclisation then affords 5,5-dimethylproline in near quantitative yield and enantioselectivity. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.05.003

文献信息

• A catalytic asymmetric synthesis of 5,5-dimethylproline
  作者：Jomana Elaridi、W. Roy Jackson、Andrea J. Robinson

  DOI：10.1016/j.tetasy.2005.05.003

  日期：2005.6

  The methyl ester derivative of commercially available N-acetyl-allylglycine readily undergoes cross-metathesis with 2-methylbut-2-ene and ruthenium-alkylidene catalyst to afford the prenylglycine derivative. Acid-catalysed cyclisation then affords 5,5-dimethylproline in near quantitative yield and enantioselectivity. (c) 2005 Published by Elsevier Ltd.