(furan-2-yl)methyl 2-chloroacetate | 51618-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (furan-2-yl)methyl 2-chloroacetate
• 英文别名: chloro-acetic acid furfuryl ester；Chlor-essigsaeure-furfurylester；Furfuryl 2-chloroacetate；furan-2-ylmethyl 2-chloroacetate
• CAS: 51618-39-4
• 化学式: C₇H₇ClO₃
• 分子量: 174.584
• InChiKey: HNRKHNATQNZLQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (furan-2-yl)methyl 2-chloroacetate 在 sodium hydroxide 作用下， 以 苯 为溶剂， 生成 1,1-diethyl 2-(furan-2-yl)methyl ethene-1,1,2-tricarboxylate
  参考文献：
  名称：

  Inter- and Intramolecular Diels-Alder Reaction of Ethenetricarboxylate Derivatives

  摘要：

  Inter- and intramolecular [4+2] cycloaddition reactions of highly electron-deficient ethenetricarboxylates have been studied. Intermolecular Diels-Alder reaction of ethenetricarboxylate esters and cyclopentadiene proceeded at room temperature or -20 degrees C to give cycloadducts with 1:1.5-1.9 endo:exo ratio. Lewis acids such as EtAlCl2, Zn(OTf)(2) and Cu(OTf)(2) catalyzed reaction at room temperature or -40 degrees C gave cycloadducts with 3.1-5.4:1 endo:exo ratio. Reaction of N-benzYl- or N-allyl-2-furylmethylamine and 1,1-diethyl 2-hydrogen ethenetricarboxylate in the presence of EDCl/HOBt/Et3N at room temperature led directly to an intramolecular Diels-Alder adduct stereoselectively. The observed stereoselectivities were explained by the use of DFT calculations.

  DOI：

  10.3987/com-15-13394
• 作为产物：
  描述：

  糠醇 、 氯乙酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 以100%的产率得到(furan-2-yl)methyl 2-chloroacetate
  参考文献：
  名称：

  Inter- and Intramolecular Diels-Alder Reaction of Ethenetricarboxylate Derivatives

  摘要：

  Inter- and intramolecular [4+2] cycloaddition reactions of highly electron-deficient ethenetricarboxylates have been studied. Intermolecular Diels-Alder reaction of ethenetricarboxylate esters and cyclopentadiene proceeded at room temperature or -20 degrees C to give cycloadducts with 1:1.5-1.9 endo:exo ratio. Lewis acids such as EtAlCl2, Zn(OTf)(2) and Cu(OTf)(2) catalyzed reaction at room temperature or -40 degrees C gave cycloadducts with 3.1-5.4:1 endo:exo ratio. Reaction of N-benzYl- or N-allyl-2-furylmethylamine and 1,1-diethyl 2-hydrogen ethenetricarboxylate in the presence of EDCl/HOBt/Et3N at room temperature led directly to an intramolecular Diels-Alder adduct stereoselectively. The observed stereoselectivities were explained by the use of DFT calculations.

  DOI：

  10.3987/com-15-13394

文献信息

• Speroni et al., Chimica e l'Industria (Milan, Italy), 1951, vol. 33, p. 209
  作者：Speroni et al.

  DOI：——

  日期：——
• DE956503
  申请人：——

  公开号：——

  公开（公告）日：——
• Inter- and Intramolecular Diels-Alder Reaction of Ethenetricarboxylate Derivatives
  作者：Shoko Yamazaki、Hirotaka Sugiura、Mamiko Niina、Yuji Mikata、Akiya Ogawa

  DOI：10.3987/com-15-13394

  日期：——

  Inter- and intramolecular [4+2] cycloaddition reactions of highly electron-deficient ethenetricarboxylates have been studied. Intermolecular Diels-Alder reaction of ethenetricarboxylate esters and cyclopentadiene proceeded at room temperature or -20 degrees C to give cycloadducts with 1:1.5-1.9 endo:exo ratio. Lewis acids such as EtAlCl2, Zn(OTf)(2) and Cu(OTf)(2) catalyzed reaction at room temperature or -40 degrees C gave cycloadducts with 3.1-5.4:1 endo:exo ratio. Reaction of N-benzYl- or N-allyl-2-furylmethylamine and 1,1-diethyl 2-hydrogen ethenetricarboxylate in the presence of EDCl/HOBt/Et3N at room temperature led directly to an intramolecular Diels-Alder adduct stereoselectively. The observed stereoselectivities were explained by the use of DFT calculations.