methyl 2,3-dihydro-2-methylbenzofuran-4-carboxylate | 79950-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: methyl 2,3-dihydro-2-methylbenzofuran-4-carboxylate
• 英文别名: Methyl 2-methyl-2,3-dihydro-1-benzofuran-4-carboxylate
• CAS: 79950-40-6
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: GSAXONXFYZNVLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  methyl 2,3-dihydro-2-methylbenzofuran-4-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 4.0h， 以79%的产率得到methyl 2-methylbenzofuran-4-carboxylate
  参考文献：
  名称：

  Stanetty, Peter; Puerstinger, Gerhard, Journal of Chemical Research, Miniprint, 1991, # 3, p. 581 - 594

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-(prop-2-ynyloxy)benzoate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 cesium fluoride 、 N,N-二乙基苯胺 作用下， 以 水 为溶剂， 20.0 ℃ 、7.09 MPa 条件下， 反应 32.0h， 生成 methyl 2,3-dihydro-2-methylbenzofuran-4-carboxylate
  参考文献：
  名称：

  Synthesis, Crystal Structures, Insecticidal Activities, and Structure−Activity Relationships of Novel N′-tert-Butyl-N′-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide Derivatives

  摘要：

  Several series of novel N'-tert-butyl-N'-substituted-benzoyl-N[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine)carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by H-1 NMR spectra, HAMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N'-tert-butyl-N,N'-diacylhydrazines show significant selectivities to different lepidopterous pests.

  DOI：

  10.1021/jf104196t

文献信息

• An investigation into the regioselectivity of the acid catalysed Claisen rearrangement of methyl 4- and 5-allyloxy-2-hydroxybenzoate and derivatives
  作者：Laurence M. Harwood

  DOI：10.1039/c39830000530

  日期：——

  The observed products from the acid catalysed Claisen rearrangement of the methyl esters (1c–g) indicate that, unlike the thermal reaction, regiochemical control is independent of internal hydrogen bonding.

  酸催化甲基酯的克莱森重排（1c – g）观察到的产物表明，与热反应不同，区域化学控制不受内部氢键的影响。
• Claisen rearrangement of meta-substituted allyl phenyl ethers
  作者：J. Malcolm Bruce、Yusuf Roshan-Ali

  DOI：10.1039/p19810002677

  日期：——

  Electron-releasing substituents at the 3-position of allyl phenyl ethers favour Claisen rearrangement of the allyl group to the 6-position, whereas electron-acceptors favour migration to the 2-position. 2-Acylhydroquinone 4-allyl ethers yield, predominantly, the 3-allyl isomers, probably because internal hydrogen bonding confers naphthalenoid character on the aryl residue.

  烯丙基苯基醚3位的电子释放取代基有利于烯丙基的Claisen重排至6位，而电子受体则有利于向2位迁移。2-酰基氢醌4-烯丙基醚主要产生3-烯丙基异构体，这可能是因为内部氢键使芳基残基具有萘类特征。