but-2-enedioic acid ethyl ester (1-methyl-oxiranyl)methyl ester | 151397-59-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: but-2-enedioic acid ethyl ester (1-methyl-oxiranyl)methyl ester
• 英文别名: 1-O-ethyl 4-O-[(2-methyloxiran-2-yl)methyl] (E)-but-2-enedioate
• CAS: 151397-59-0
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: JOQYMLYHYLUCBN-SNAWJCMRSA-N

物化性质

• 沸点：
  313.9±17.0 °C(predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-1-pentyne 、 but-2-enedioic acid ethyl ester (1-methyl-oxiranyl)methyl ester 在 Schwartz's reagent 、 亚磷酸三苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以69%的产率得到3-[(2RS,4RS)-2-(5-benzyloxy-pent-1-(E)-enyl)-4-hydroxymethyl-4-methyl-[1,3]dioxolan-2-yl]-acrylic 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
• 作为产物：
  描述：

  富马酸单乙酯 在 4-二甲氨基吡啶 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 but-2-enedioic acid ethyl ester (1-methyl-oxiranyl)methyl 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

• Synthesis and reactivity of dioxycarbenium ions from epoxy esters and cationic zirconium complexes
  作者：Peter Wipf、Wenjing Xu

  DOI：10.1021/jo00074a006

  日期：1993.10

  Rearrangement of epoxy esters in the presence Of Cp2Zr(R)+ or CP2Zr(Cl)+ results in synthetically useful dioxycarbenium intermediates. Acetals, ortho esters, and tetrahydrofurans are prepared by ligand transfer from zirconium, intramolecular trapping, or further rearrangement reactions.
• 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.