10-Methoxy-3-oxo-1,10b-dihydro-oxazolo[4,3-a]isoquinoline-5-carbaldehyde | 170507-98-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 10-Methoxy-3-oxo-1,10b-dihydro-oxazolo[4,3-a]isoquinoline-5-carbaldehyde
• 英文别名: 10-Methoxy-3-oxo-1,10b-dihydro-[1,3]oxazolo[4,3-a]isoquinoline-5-carbaldehyde
• CAS: 170507-98-9
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: FBLIJEKIWSIXLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  肌氨酸苄酯 、 丙烯酸甲酯（MA） 、 10-Methoxy-3-oxo-1,10b-dihydro-oxazolo[4,3-a]isoquinoline-5-carbaldehyde 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以62%的产率得到(2R,4S,5R)-5-(10-Methoxy-3-oxo-1,10b-dihydro-oxazolo[4,3-a]isoquinolin-5-yl)-1-methyl-pyrrolidine-2,4-dicarboxylic acid 2-benzyl ester 4-methyl ester
  参考文献：
  名称：

  Synthetic Studies on Quinocarcin: Total Synthesis of (.+-.)-Quinocarcinamide via Dipole Cycloaddition of an Azomethine Ylide Generated by NBS Oxidation

  摘要：

  The total synthesis of (+/-)-quinocarcinamide and a formal total synthesis of the antitumor, antibiotic quinocarcin involving a [3 + 2] dipolar cycloaddition reaction is described. The synthesis involves as a key step an NBS oxidation of an allylic tertiary amine to an imminium ion which is converted in situ into an azomethine ylide. Aspects of the ylide formation and a rationale for the regio- and stereocontrol for the cycloaddition process are discussed.

  DOI：

  10.1021/jo00126a031
• 作为产物：
  描述：

  6-Hydroxy-10-methoxy-3-oxo-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinoline-5-carboxylic acid 在 sodium tetrahydroborate 、 氯化亚砜 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 10-Methoxy-3-oxo-1,10b-dihydro-oxazolo[4,3-a]isoquinoline-5-carbaldehyde
  参考文献：
  名称：

  Synthetic Studies on Quinocarcin: Total Synthesis of (.+-.)-Quinocarcinamide via Dipole Cycloaddition of an Azomethine Ylide Generated by NBS Oxidation

  摘要：

  The total synthesis of (+/-)-quinocarcinamide and a formal total synthesis of the antitumor, antibiotic quinocarcin involving a [3 + 2] dipolar cycloaddition reaction is described. The synthesis involves as a key step an NBS oxidation of an allylic tertiary amine to an imminium ion which is converted in situ into an azomethine ylide. Aspects of the ylide formation and a rationale for the regio- and stereocontrol for the cycloaddition process are discussed.

  DOI：

  10.1021/jo00126a031

文献信息

• Synthetic Studies on Quinocarcin: Total Synthesis of (.+-.)-Quinocarcinamide via Dipole Cycloaddition of an Azomethine Ylide Generated by NBS Oxidation
  作者：Mark E. Flanagan、Robert M. Williams

  DOI：10.1021/jo00126a031

  日期：1995.10

  The total synthesis of (+/-)-quinocarcinamide and a formal total synthesis of the antitumor, antibiotic quinocarcin involving a [3 + 2] dipolar cycloaddition reaction is described. The synthesis involves as a key step an NBS oxidation of an allylic tertiary amine to an imminium ion which is converted in situ into an azomethine ylide. Aspects of the ylide formation and a rationale for the regio- and stereocontrol for the cycloaddition process are discussed.