(2S,4R)-2-amino-4-methylhept-6-enoic acid | 1258872-33-1

• 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,4R)-2-amino-4-methylhept-6-enoic acid
• CAS: 1258872-33-1
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: NCNXJFPONDESML-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 二碳酸二叔丁酯 、 (2S,4R)-2-amino-4-methylhept-6-enoic acid 在 氯化亚砜 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以82%的产率得到(2S,4R)-methyl-2-(tert-butoxycarbonylamino)-4-methylhept-6-enoate
  参考文献：
  名称：

  Synthesis of Methyl N-Boc-(2S,4R)-4-methylpipecolate

  摘要：

  An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric a-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO4/NaIO4 followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.

  DOI：

  10.1021/jo102038q
• 作为产物：
  描述：

  (4R)-5-iodo-4-methylpent-1-ene 、 聚甘氨酸 在 nickel(II) nitrate hexahydrate 、 potassium hydroxide 、 (R)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide hydrochloride 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 乙腈 、 水 为溶剂， 反应 5.0h， 以0.84 g的产率得到(2S,4R)-2-amino-4-methylhept-6-enoic acid
  参考文献：
  名称：

  Synthesis of Methyl N-Boc-(2S,4R)-4-methylpipecolate

  摘要：

  An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric a-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO4/NaIO4 followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.

  DOI：

  10.1021/jo102038q