2-vinyl-3,5,6,7-tetrahydrobenzofuran-4(2H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-vinyl-3,5,6,7-tetrahydrobenzofuran-4(2H)-one
• 英文别名: 2-ethenyl-3,5,6,7-tetrahydro-2H-1-benzofuran-4-one
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: VIUBFUHKYVPTQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 、 1,3-环己二酮 在 diphosphinidenecyclobutene-coordinated palladium 吡啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以42%的产率得到2-vinyl-3,5,6,7-tetrahydrobenzofuran-4(2H)-one
  参考文献：
  名称：

  Cyclodehydration of cis–2-butene-1,4-diol with active methylene compounds catalyzed by a diphosphinidenecyclobutene-coordinated palladium complex

  摘要：

  (pi-Allyl)palladium triflate coordinated with 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-t-butylphenylphosphinidene)cyclobutene (DPCB-OMe), [Pd(eta(3)-C3H5)(DPCB-OMe)]OTf, efficiently catalyzes cycl odehydration of cis-2-butene-1,4-diol with active methylene compounds such as acetylacetone and ethyl acetoacetate in toluene in the presence of pyridine. The reactions can be performed in air, giving 2-vinyl-2,3-dihydrofurans in good to high yields. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.03.011

文献信息

• One‐Pot Synthesis of Metastable 2,5‐Dihydrooxepines through Retro‐Claisen Rearrangements: Method and Applications
  作者：Wei Zhang、Emmanuel Baudouin、Marie Cordier、Gilles Frison、Bastien Nay

  DOI：10.1002/chem.201901675

  日期：2019.6.26

  synthesize metastable bicyclic 2,5‐dihydrooxepines from cyclic 1,3‐diketones and 1,4‐dibromo‐2‐butenes through the retro‐Claisen rearrangement of syn‐2‐vinylcyclopropyl diketone intermediates is reported. DFT calculations were performed to understand the reaction selectivity and mechanisms towards [1,3]‐ or [3,3]‐sigmatropic rearrangements, highlighting the crucial influence of the temperature. The reaction

  报道了一种通过一锅法从环状1,3-二酮和1,4-二溴-2-丁烯通过顺-2-乙烯基环丙基二酮中间体的反向克莱森重排合成亚稳的双环2,5-二氢氧杂环丁烷的方法。进行DFT计算是为了了解对[1,3]-或[3,3]-σ重排的反应选择性和机理，突出了温度的关键影响。该反应已成功应用于radulanin A（一种天然的2,5-二氢苯并xepine）的无保护基团的短合成。此外，首次证明了这种天然产品具有很强的除草潜力。
• Cyclodehydration of cis–2-butene-1,4-diol with active methylene compounds catalyzed by a diphosphinidenecyclobutene-coordinated palladium complex
  作者：Hiromi Murakami、Yukio Matsui、Fumiyuki Ozawa、Masaaki Yoshifuji

  DOI：10.1016/j.jorganchem.2006.03.011

  日期：2006.7

  (pi-Allyl)palladium triflate coordinated with 1,2-bis(4-methoxyphenyl)-3,4-bis(2,4,6-tri-t-butylphenylphosphinidene)cyclobutene (DPCB-OMe), [Pd(eta(3)-C3H5)(DPCB-OMe)]OTf, efficiently catalyzes cycl odehydration of cis-2-butene-1,4-diol with active methylene compounds such as acetylacetone and ethyl acetoacetate in toluene in the presence of pyridine. The reactions can be performed in air, giving 2-vinyl-2,3-dihydrofurans in good to high yields. (c) 2006 Elsevier B.V. All rights reserved.