(1R,7S)-tetrahydro-1-(2-propenyl)-1H,3H-pyrrolo[1,2-c]oxazol-3-one | 123484-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (1R,7S)-tetrahydro-1-(2-propenyl)-1H,3H-pyrrolo[1,2-c]oxazol-3-one
• 英文别名: (1R,7aS)-1-prop-2-enyl-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 123484-34-4
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: BGAPGXDNEILMMN-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 indium 、 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 336001.25h， 生成 (1R,7S)-tetrahydro-1-(2-propenyl)-1H,3H-pyrrolo[1,2-c]oxazol-3-one
  参考文献：
  名称：

  A new strategy for the synthesis of hydroxylated pyrrolizidinic alkaloids by highly stereoselective indium-mediated allylation of pyrrolidinic aldehydes

  摘要：

  Indium-mediated allylation of N-Cbz-L-prolinal 3, under Grignard conditions, was carried out with high yield and stereoselectivity (de = 90%) to afford intermediate (2S, 1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine 4, which was transformed in two steps into (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine 9. Commercial Cbz-L-proline was a source of functionalization and chirality. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.010

文献信息

• <i>N</i>-Tritylprolinal:  An Efficient Building Block for the Stereoselective Synthesis of Proline-Derived Amino Alcohols
  作者：Joseph Bejjani、Fabrice Chemla、Max Audouin

  DOI：10.1021/jo034976g

  日期：2003.12.1

  N-Tritylprolinal (prepared in four steps from L-proline) shows a very high Felkin diastereoselectivity in its reaction with various nucleophiles, leading to a straightforward and highly stereoselective access to syn-proline-derived amino alcohols.
• A new strategy for the synthesis of hydroxylated pyrrolizidinic alkaloids by highly stereoselective indium-mediated allylation of pyrrolidinic aldehydes
  作者：Isidoro Izquierdo、María T. Plaza、Víctor Yáñez

  DOI：10.1016/j.tetasy.2005.10.010

  日期：2005.11

  Indium-mediated allylation of N-Cbz-L-prolinal 3, under Grignard conditions, was carried out with high yield and stereoselectivity (de = 90%) to afford intermediate (2S, 1'R)-N-benzyloxycarbonyl-2-(1'-hydroxybut-3'-en-1'-yl)pyrrolidine 4, which was transformed in two steps into (1R,3R,7aS)-1-hydroxy-3-hydroxymethylpyrrolizidine 9. Commercial Cbz-L-proline was a source of functionalization and chirality. (c) 2005 Elsevier Ltd. All rights reserved.