3-[2-(furfuryloxymethyl)benzyloxy]-1-diazo-2-propanone | 251961-39-4

• 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: 3-[2-(furfuryloxymethyl)benzyloxy]-1-diazo-2-propanone
• 英文别名: 1-Diazo-3-[[2-(furan-2-ylmethoxymethyl)phenyl]methoxy]propan-2-one；1-diazo-3-[[2-(furan-2-ylmethoxymethyl)phenyl]methoxy]propan-2-one
• CAS: 251961-39-4
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: QZDMRAGGBWMOOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[2-(furfuryloxymethyl)benzyloxy]-1-diazo-2-propanone 在 dirhodium(II) tetrakis(perfluorobutyrate) 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以46%的产率得到(2Z,4E)-10,11-benzo-8,13-dioxacyclotetradeca-2,4-diene-1,6-dione
  参考文献：
  名称：

  Catalytic Intramolecular Addition of Metal Carbenes to Remote Furans

  摘要：

  [GRAPHICS]Diazo esters and diazo ketones linked to a furan undergo catalytic intramolecular addition of an intermediate metal carbene to the remote furan to form diendiones with ring sizes up to 17. Regioselectivity is catalyst dependent with addition to either the more or less substituted double bond. The high product yields and absence of need for high dilution suggest that this methodology is general for macrocycle preparations.

  DOI：

  10.1021/ol990168t
• 作为产物：
  描述：

  邻苯二甲醇 在 sodium hydroxide 、 三溴化磷 、 sodium hydride 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 3-[2-(furfuryloxymethyl)benzyloxy]-1-diazo-2-propanone
  参考文献：
  名称：

  Catalytic Intramolecular Addition of Metal Carbenes to Remote Furans

  摘要：

  [GRAPHICS]Diazo esters and diazo ketones linked to a furan undergo catalytic intramolecular addition of an intermediate metal carbene to the remote furan to form diendiones with ring sizes up to 17. Regioselectivity is catalyst dependent with addition to either the more or less substituted double bond. The high product yields and absence of need for high dilution suggest that this methodology is general for macrocycle preparations.

  DOI：

  10.1021/ol990168t

文献信息

• Catalytic Intramolecular Addition of Metal Carbenes to Remote Furans
  作者：Michael P. Doyle、Brant J. Chapman、Wenhao Hu、Chad S. Peterson、M. Anthony McKervey、Concepción F. Garcia

  DOI：10.1021/ol990168t

  日期：1999.11.1

  [GRAPHICS]Diazo esters and diazo ketones linked to a furan undergo catalytic intramolecular addition of an intermediate metal carbene to the remote furan to form diendiones with ring sizes up to 17. Regioselectivity is catalyst dependent with addition to either the more or less substituted double bond. The high product yields and absence of need for high dilution suggest that this methodology is general for macrocycle preparations.