4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methylpent-(2E)-enyl]-pyridine | 1197011-17-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methylpent-(2E)-enyl]-pyridine
• 英文别名: (E)-5-(5,6-dimethoxy-3-methyl-4-oxo-1H-pyridin-2-yl)-3-methylpent-3-enal
• CAS: 1197011-17-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: CXVANBDTHOEHMC-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methylpent-(2E)-enyl]-pyridine 、 (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonylocta-(2E,6E)-diene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 以0.0062 g的产率得到β-甘油磷酸钠
  参考文献：
  名称：

  Total synthesis of (+)-piericidin A1 and (−)-piericidin B1

  摘要：

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.07.044
• 作为产物：
  描述：

  C₂₂H₃₉NO₆Si 在 盐酸 、 水 作用下， 以 异丙醇 为溶剂， 以65%的产率得到4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methylpent-(2E)-enyl]-pyridine
  参考文献：
  名称：

  Total synthesis of (+)-piericidin A1 and (−)-piericidin B1

  摘要：

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.07.044

文献信息

• Total synthesis of (+)-piericidin A1 and (−)-piericidin B1
  作者：Ryosuke Kikuchi、Mikio Fujii、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2009.07.044

  日期：2009.9

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.