1-[(1R,7aS)-1-甲基四氢-1H-吡咯并[1,2-c][1,3]恶唑-1-基]乙酮 | 91550-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-[(1R,7aS)-1-甲基四氢-1H-吡咯并[1,2-c][1,3]恶唑-1-基]乙酮
• 英文名称: 1-[(1R,7aS)-1-methyl-5,6,7,7a-tetrahydro-3H-pyrrolo[1,2-c][1,3]oxazol-1-yl]ethanone
• CAS: 91550-07-1
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: XTXFQGSFQHPTIA-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(1R,7aS)-1-甲基四氢-1H-吡咯并[1,2-c][1,3]恶唑-1-基]乙酮 在 三氟甲磺酸三甲基硅酯 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 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 、 甲醇 、 乙醚 、 乙醇 、 水 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 1-[(1R,7aS)-1-甲基四氢-1H-吡咯并[1,2-c][1,3]恶唑-1-基]乙酮
  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

文献信息

• Enantioselective total synthesis of allopumiliotoxin A alkaloids 267A and 339B
  作者：Larry E. Overman、Steven W. Goldstein

  DOI：10.1021/ja00330a059

  日期：1984.9
• The first enantioselective total syntheses of the allopumiliotoxin A alkaloids 267A and 339B
  作者：Steven W. Goldstein、Larry E. Overman、Michael H. Rabinowitz

  DOI：10.1021/jo00030a026

  日期：1992.2

  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.