(2S,5R)-(-)-cis-5-isopropylproline | 110452-52-3

• 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,5R)-(-)-cis-5-isopropylproline
• 英文别名: (2S,5R)-5-Isopropylpyrrolidine-2-carboxylic acid；(2S,5R)-5-propan-2-ylpyrrolidine-2-carboxylic acid
• CAS: 110452-52-3
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: PIDBLIRWSBCSPG-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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S,5R)-(-)-cis-5-isopropylproline 在 氯化亚砜 作用下， 以66%的产率得到(2S,5R)-(-)-cis-5-isopropylproline methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one

  摘要：

  The conjugate addition of enamines (2a,b) to the chiral oxazolidinones (1) or ent-(1) favours cis 2,4-substituted oxazolidinone adducts while trans 2,4-substituted oxazolidinone adducts are favoured from the addition reactions of enamine (2c). The diastereomeric adducts from the addition of (2a) to (1) are readily separated and can be converted to (5R, 2S) and (5S, 2R) 5-iso-propyl proline efficiently and in good overall yield. The extenstion of this protocol to the synthesis of perhydroindole carboxylic acid suffered from poor overall stereochemical control.

  DOI：

  10.1016/0040-4020(95)98711-p
• 作为产物：
  描述：

  (2S,5R)-cis-5-isopropylproline hydrochloride 在 Dowex 50-X₈ (H⁽¹⁺⁾) 作用下， 以 水 为溶剂， 以93%的产率得到(2S,5R)-(-)-cis-5-isopropylproline
  参考文献：
  名称：

  Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one

  摘要：

  The conjugate addition of enamines (2a,b) to the chiral oxazolidinones (1) or ent-(1) favours cis 2,4-substituted oxazolidinone adducts while trans 2,4-substituted oxazolidinone adducts are favoured from the addition reactions of enamine (2c). The diastereomeric adducts from the addition of (2a) to (1) are readily separated and can be converted to (5R, 2S) and (5S, 2R) 5-iso-propyl proline efficiently and in good overall yield. The extenstion of this protocol to the synthesis of perhydroindole carboxylic acid suffered from poor overall stereochemical control.

  DOI：

  10.1016/0040-4020(95)98711-p

文献信息

• Asymmetric synthesis of proline derivatives from (2R) and (2S)-2-tert-butyl-3-benzoyl-4-methyleneoxazolidin-5-one
  作者：Stephen G Pyne、Abdollah Javidan、Brian W Skelton、Allan H White

  DOI：10.1016/0040-4020(95)98711-p

  日期：1995.4

  The conjugate addition of enamines (2a,b) to the chiral oxazolidinones (1) or ent-(1) favours cis 2,4-substituted oxazolidinone adducts while trans 2,4-substituted oxazolidinone adducts are favoured from the addition reactions of enamine (2c). The diastereomeric adducts from the addition of (2a) to (1) are readily separated and can be converted to (5R, 2S) and (5S, 2R) 5-iso-propyl proline efficiently and in good overall yield. The extenstion of this protocol to the synthesis of perhydroindole carboxylic acid suffered from poor overall stereochemical control.