(2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde | 1401113-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
• 英文别名: (3S,4'S,5'R)-5'-(hydroxymethyl)-4'-phenylmethoxyspiro[1,4-dihydropyrrolo[2,1-c][1,4]oxazine-3,2'-oxolane]-6-carbaldehyde
• CAS: 1401113-19-6
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: XEXXHEUVXUWYTF-OTWHNJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到acortatarin A
  参考文献：
  名称：

  Total Synthesis of Acortatarin A Using a Pd(II)-Catalyzed Spiroketalization Strategy

  摘要：

  The total synthesis of acortatarin A relying on a Pd(II)-catalyzed spiroketalization is reported. This strategy allows a single stereocenter in the spiroketalization substrate to produce the target efficiently under mild conditions, installing the necessary oxygenation in the backbone through an allylic transposition. The synthesis also verifies that pollenopyrroside B and acortatarin A are the same compound, and electrochemical studies suggest that the reported bioactivity is not due to simple antioxidant properties.

  DOI：

  10.1021/jo301835e
• 作为产物：
  描述：

  N-甲氧基-N-甲基-1H-吡咯-2-甲酰胺 在 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 二(氰基苯)二氯化钯 、 lithium tris(3-ethyl-3-pentoyloxy)aluminohydride 、 caesium carbonate 、 N-甲基吗啉氧化物 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 62.5h， 生成 (2S,4S,5R)-4-(benzyloxy)-5-(hydroxymethyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
  参考文献：
  名称：

  Total Synthesis of Acortatarin A Using a Pd(II)-Catalyzed Spiroketalization Strategy

  摘要：

  The total synthesis of acortatarin A relying on a Pd(II)-catalyzed spiroketalization is reported. This strategy allows a single stereocenter in the spiroketalization substrate to produce the target efficiently under mild conditions, installing the necessary oxygenation in the backbone through an allylic transposition. The synthesis also verifies that pollenopyrroside B and acortatarin A are the same compound, and electrochemical studies suggest that the reported bioactivity is not due to simple antioxidant properties.

  DOI：

  10.1021/jo301835e

文献信息

• Total Synthesis of Acortatarin A Using a Pd(II)-Catalyzed Spiroketalization Strategy
  作者：Nicholas V. Borrero、Aaron Aponick

  DOI：10.1021/jo301835e

  日期：2012.10.5

  The total synthesis of acortatarin A relying on a Pd(II)-catalyzed spiroketalization is reported. This strategy allows a single stereocenter in the spiroketalization substrate to produce the target efficiently under mild conditions, installing the necessary oxygenation in the backbone through an allylic transposition. The synthesis also verifies that pollenopyrroside B and acortatarin A are the same compound, and electrochemical studies suggest that the reported bioactivity is not due to simple antioxidant properties.