(R)-α-Methyl-α-acetyl-2(S)-pyrrolidinemethanol hydrochloride | 138052-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-α-Methyl-α-acetyl-2(S)-pyrrolidinemethanol hydrochloride
• CAS: 138052-91-2
• 化学式: C₈H₁₅NO₂*ClH
• 分子量: 193.674
• InChiKey: UJSAMIVYOTXUBQ-WSZWBAFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-α-Methyl-α-acetyl-2(S)-pyrrolidinemethanol hydrochloride 在 对甲苯磺酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 3.25h， 生成 (8R*,8aS*)-8-Hydroxy-8-methyl-7(1H)-octahydroindolizinone
  参考文献：
  名称：

  The first enantioselective total syntheses of the allopumiliotoxin A alkaloids 267A and 339B

  摘要：

  Short, highly stereocontrolled, asymmetric total synthesis of the title amphibian alkaloids are described. In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form. This short sequence proceeds in five laboratory operations and involves the novel intermediacy of an "unprotected" 2-acylpyrrolidine intermediate (Scheme VII). The (Z)-alkylidene side chain of the target alkaloids are introduced by stereocontrolled aldol dehydration sequences (Schemes X and XI). These enantioselective total syntheses confirm the structures and absolute configurations of the allopumiliotoxins 267A and 339B.

  DOI：

  10.1021/jo00030a026
• 作为产物：
  描述：

  1-苄基-L-脯氨酸 在 palladium on activated charcoal 盐酸 、 氢气 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 7.25h， 生成 (R)-α-Methyl-α-acetyl-2(S)-pyrrolidinemethanol hydrochloride
  参考文献：
  名称：

  The first enantioselective total syntheses of the allopumiliotoxin A alkaloids 267A and 339B

  摘要：

  Short, highly stereocontrolled, asymmetric total synthesis of the title amphibian alkaloids are described. In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form. This short sequence proceeds in five laboratory operations and involves the novel intermediacy of an "unprotected" 2-acylpyrrolidine intermediate (Scheme VII). The (Z)-alkylidene side chain of the target alkaloids are introduced by stereocontrolled aldol dehydration sequences (Schemes X and XI). These enantioselective total syntheses confirm the structures and absolute configurations of the allopumiliotoxins 267A and 339B.

  DOI：

  10.1021/jo00030a026