1H-Pyrano[3,4-c]pyridine-3,8(4H,7H)-dione, 4-ethyl-7-(phenylmethyl)- | 918803-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 1H-Pyrano[3,4-c]pyridine-3,8(4H,7H)-dione, 4-ethyl-7-(phenylmethyl)-
• 英文别名: 7-benzyl-4-ethyl-1,4-dihydropyrano[3,4-c]pyridine-3,8-dione
• CAS: 918803-86-8
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: DCQLCHMQCQHJBE-UHFFFAOYSA-N

物化性质

• 沸点：
  578.6±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-Pyrano[3,4-c]pyridine-3,8(4H,7H)-dione, 4-ethyl-7-(phenylmethyl)- 在 palladium dihydroxide 氢气 、 氧气 、 二甲胺 、 copper dichloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 4-ethyl-4-hydroxy-1,7-dihydro-4H-pyrano[3,4-c]pyridine-3,8-dione
  参考文献：
  名称：

  A practical formal synthesis of camptothecin

  摘要：

  The synthesis of the DE ring of camptothecin using simple and inexpensive starting materials, employing an addition elimination reaction and selective esterification of an aliphatic carboxylic acid as key steps is described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.017
• 作为产物：
  描述：

  1-Benzyl-4-(1-carboxypropyl)-2-oxopyridine-3-carboxylic acid 在 三乙胺 、 氯甲酸甲酯 、 nickel dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 1H-Pyrano[3,4-c]pyridine-3,8(4H,7H)-dione, 4-ethyl-7-(phenylmethyl)-
  参考文献：
  名称：

  A practical formal synthesis of camptothecin

  摘要：

  The synthesis of the DE ring of camptothecin using simple and inexpensive starting materials, employing an addition elimination reaction and selective esterification of an aliphatic carboxylic acid as key steps is described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.017

文献信息

• Introduction of the Acetate Unit to the 2-Pyridinone Ring System and Its Application to the Synthesis of (20<i>S</i>)-Camptothecin DE Ring System
  作者：Kou Hiroya、Kei Kawamoto、Takao Sakamoto

  DOI：10.1055/s-2006-950433

  日期：2006.9

  The DE ring system of (20S)-camptothecin had been ­prepared from commercially available nicotinic acid in six steps ­utilizing the nucleophilic addition reaction of the silyl ketene acetal to the pyridinone ring as a key step.

  (20S)-喜树碱的 DE 环系统是利用硅酮缩醛与吡啶酮环的亲核加成反应作为关键步骤，通过六个步骤从市售烟酸中制备出来的。
• Tandem Aza-Michael-Condensation-Aldol Cyclization Reaction: Approach to the Construction of DE Synthon of (±)-Camptothecin
  作者：Subhash Chavan、Abasaheb Dhawane、Uttam Kalkote

  DOI：10.1055/s-0028-1083539

  日期：——

  An efficient synthesis of the DE ring of camptothecin, employing a Reformatsky and a tandem one-pot, three-step trans- formation involving aza-Michael reaction, condensation with ethyl malonyl chloride followed by intramolecular 'aldol' reaction to fur- nish the dihydropyridone derivative from commercially available starting materials, has been achieved.

  喜树碱 DE 环的有效合成，采用 Reformatsky 和串联一锅三步转化，包括 aza-Michael 反应，与乙基丙二酰氯缩合，然后进行分子内“羟醛”反应以提供二氢吡啶酮衍生自市售原料，已经实现。
• A practical formal synthesis of camptothecin
  作者：Subhash P. Chavan、Ashok B. Pathak、Uttam R. Kalkote

  DOI：10.1016/j.tetlet.2007.07.017

  日期：2007.9

  The synthesis of the DE ring of camptothecin using simple and inexpensive starting materials, employing an addition elimination reaction and selective esterification of an aliphatic carboxylic acid as key steps is described. (C) 2007 Elsevier Ltd. All rights reserved.