3-[(2RS,4RS)-2-(3-benzyloxy-but-1-(E)-enyl)-4-hydroxymethyl-4-methyl-[1,3]dioxolan-2-yl]-acrylic acid ethyl ester

• 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-[(2RS,4RS)-2-(3-benzyloxy-but-1-(E)-enyl)-4-hydroxymethyl-4-methyl-[1,3]dioxolan-2-yl]-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[(2S,4S)-4-(hydroxymethyl)-4-methyl-2-[(E)-3-phenylmethoxybut-1-enyl]-1,3-dioxolan-2-yl]prop-2-enoate
• 化学式: C₂₁H₂₈O₆
• 分子量: 376.45
• InChiKey: ARLBWSJOZXGDOP-TVDXJSIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[(2RS,4RS)-2-(3-benzyloxy-but-1-(E)-enyl)-4-hydroxymethyl-4-methyl-[1,3]dioxolan-2-yl]-acrylic acid ethyl ester 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 6-(1-benzyloxyethyl)-3-butyl-4-oxo-decanoic 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：

  ((but-3-yn-2-yloxy)methyl)benzene 、 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31%的产率得到3-[(2RS,4RS)-2-(3-benzyloxy-but-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

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.