(E)-(S)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-2-iodo-hex-4-en-1-one | 150566-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-(S)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-2-iodo-hex-4-en-1-one
• CAS: 150566-47-5
• 化学式: C₁₄H₂₄INO₃
• 分子量: 381.254
• InChiKey: RDDCUTRRDZIYAJ-MTTQNTSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-(S)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-2-iodo-hex-4-en-1-one 在 sodium azide 、 sodium carbonate 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 D-N-Boc-nor-leucine methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

  摘要：

  The alpha-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I2 and s-collidine. The chiral iodides 2 thus obtained were converted to the alpha-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.

  DOI：

  10.1016/s0040-4039(00)60372-6
• 作为产物：
  描述：

  (E)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-hex-4-en-1-one 在 2,4,6-三甲基吡啶 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (E)-(R)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-2-iodo-hex-4-en-1-one 、 (E)-(S)-1-((2R,5R)-2,5-Bis-methoxymethyl-pyrrolidin-1-yl)-2-iodo-hex-4-en-1-one
  参考文献：
  名称：

  Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

  摘要：

  The alpha-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I2 and s-collidine. The chiral iodides 2 thus obtained were converted to the alpha-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.

  DOI：

  10.1016/s0040-4039(00)60372-6