(E)-ethyl 3-((E)-but-2-en-1-yloxy)acrylate | 86273-39-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-ethyl 3-((E)-but-2-en-1-yloxy)acrylate
• 英文别名: 3t-but-2t-enyloxy-acrylic acid ethyl ester；3t-But-2t-enyloxy-acrylsaeure-aethylester；ethyl (E)-3-[(E)-but-2-enoxy]prop-2-enoate
• CAS: 86273-39-4
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: CMWHGNFKYHXCED-QFXXITGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-((E)-but-2-en-1-yloxy)acrylate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 生成 ethyl 2-(hydroxymethyl)-3-methylpent-4-enoate
  参考文献：
  名称：

  A one-pot synthesis of α-formyl-α-allylacetates via nucleophilic catalysis

  摘要：

  A step-economical one-pot nucleophilic catalysis/thermal Claisen-rearrangement protocol for the direct synthesis of alpha-formyl-alpha-allylacetates from allylic alcohols and activated alkynes has been developed. The product alpha-formyl-alpha-allylacetates were further reacted in situ to give either protected enol ethers or beta-hydroxy-4-pentenoates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.035
• 作为产物：
  描述：

  巴豆醇 、 丙炔酸乙酯 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.92h， 以97%的产率得到(E)-ethyl 3-((E)-but-2-en-1-yloxy)acrylate
  参考文献：
  名称：

  A one-pot synthesis of α-formyl-α-allylacetates via nucleophilic catalysis

  摘要：

  A step-economical one-pot nucleophilic catalysis/thermal Claisen-rearrangement protocol for the direct synthesis of alpha-formyl-alpha-allylacetates from allylic alcohols and activated alkynes has been developed. The product alpha-formyl-alpha-allylacetates were further reacted in situ to give either protected enol ethers or beta-hydroxy-4-pentenoates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.035

文献信息

• Transetherification Reactions. Preparation and Rearrangement of β-Alloxyacrylates¹
  作者：W. J. Croxall、J. O. Van Hook

  DOI：10.1021/ja01158a040

  日期：1950.2
• Allylic rearrangement
  申请人：ROHM &

  公开号：US02540071A1

  公开（公告）日：1951-01-30
• Acyloxymethylene-pentenoates
  申请人：ROHM & HAAS

  公开号：US02540070A1

  公开（公告）日：1951-01-30
• A one-pot synthesis of α-formyl-α-allylacetates via nucleophilic catalysis
  作者：William Chung、Petra Lindovska、Jason E. Camp

  DOI：10.1016/j.tetlet.2011.10.035

  日期：2011.12

  A step-economical one-pot nucleophilic catalysis/thermal Claisen-rearrangement protocol for the direct synthesis of alpha-formyl-alpha-allylacetates from allylic alcohols and activated alkynes has been developed. The product alpha-formyl-alpha-allylacetates were further reacted in situ to give either protected enol ethers or beta-hydroxy-4-pentenoates. (C) 2011 Elsevier Ltd. All rights reserved.