9-benzyloxy-3-methyl-4-oxo-non-5-enoic acid ethyl ester | 250613-66-2

• 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: 9-benzyloxy-3-methyl-4-oxo-non-5-enoic acid ethyl ester
• 英文别名: ethyl (E)-3-methyl-4-oxo-9-phenylmethoxynon-5-enoate
• CAS: 250613-66-2
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: FSSBITBWQJAXIK-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-benzyloxy-3-methyl-4-oxo-non-5-enoic acid ethyl ester 在 copper(I) bromide dimethylsulfide complex 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 12.0h， 生成 6-(5-benzyloxy-2-phenyl-pentyl)-5-methyl-2-phenyl-2H-pyridazin-3-one
  参考文献：
  名称：

  Silver(I)-Catalyzed Addition of Zirconocenes to Epoxy Esters:  A New Entry to 1,4-Dicarbonyl Compounds and Pyridazinones

  摘要：

  [GRAPHICS]The Ag(I)-catalyzed tandem epoxy ester rearrangement-dioxycarbenium ion addition reaction with alkenyl zirconocenes provides 1,4-keto esters that can be further converted to substituted pyridazinones. The use of a fluorous tag in a cyclization-assisted cleavage strategy demonstrates the feasibility of extending this methodology to high-throughput organic synthesis.

  DOI：

  10.1021/ol990924v
• 作为产物：
  描述：

  3-[(2RS,4RS)-2-(5-benzyloxy-pent-1-(E)-enyl)-4-hydroxymethyl-4-methyl-[1,3]dioxolan-2-yl]-acrylic acid ethyl ester 、 甲基锂 在 copper(I) bromide dimethylsulfide complex 、 三甲基氯硅烷 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 反应 6.0h， 以97%的产率得到9-benzyloxy-3-methyl-4-oxo-non-5-enoic acid ethyl ester
  参考文献：
  名称：

  Silver(I)-Catalyzed Addition of Zirconocenes to Epoxy Esters:  A New Entry to 1,4-Dicarbonyl Compounds and Pyridazinones

  摘要：

  [GRAPHICS]The Ag(I)-catalyzed tandem epoxy ester rearrangement-dioxycarbenium ion addition reaction with alkenyl zirconocenes provides 1,4-keto esters that can be further converted to substituted pyridazinones. The use of a fluorous tag in a cyclization-assisted cleavage strategy demonstrates the feasibility of extending this methodology to high-throughput organic synthesis.

  DOI：

  10.1021/ol990924v

文献信息

• Silver(I)-Catalyzed Addition of Zirconocenes to Epoxy Esters:  A New Entry to 1,4-Dicarbonyl Compounds and Pyridazinones
  作者：Peter Wipf、Joey-Lee Methot

  DOI：10.1021/ol990924v

  日期：1999.10.1

  [GRAPHICS]The Ag(I)-catalyzed tandem epoxy ester rearrangement-dioxycarbenium ion addition reaction with alkenyl zirconocenes provides 1,4-keto esters that can be further converted to substituted pyridazinones. The use of a fluorous tag in a cyclization-assisted cleavage strategy demonstrates the feasibility of extending this methodology to high-throughput organic synthesis.