(10-Methoxy-3-oxo-1,10b-dihydro-[1,3]oxazolo[4,3-a]isoquinolin-5-yl)methyl methanesulfonate | 1026446-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (10-Methoxy-3-oxo-1,10b-dihydro-[1,3]oxazolo[4,3-a]isoquinolin-5-yl)methyl methanesulfonate
• CAS: 1026446-93-4
• 化学式: C₁₄H₁₅NO₆S
• 分子量: 325.342
• InChiKey: MRWFWYUJQZCMQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (10-Methoxy-3-oxo-1,10b-dihydro-[1,3]oxazolo[4,3-a]isoquinolin-5-yl)methyl methanesulfonate 在 W₂ Raney-Ni 盐酸 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 二异丙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 65.0 ℃ 、10.34 MPa 条件下， 反应 75.5h， 生成 (5α,8β,10β,11β,11aβ)-5,7,9,10,11,11a,12-Octahydro-4-methoxy-5-<(methoxymethoxy)methyl>-13-methyl-7-oxo-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid
  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 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.5h， 生成 (10-Methoxy-3-oxo-1,10b-dihydro-[1,3]oxazolo[4,3-a]isoquinolin-5-yl)methyl methanesulfonate
  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.