3,4-dimethoxybenzylcyclopropane | 479484-78-1

• 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: 3,4-dimethoxybenzylcyclopropane
• 英文别名: 4-Cyclopropylmethyl-1,2-dimethoxy-benzene；4-(Cyclopropylmethyl)-1,2-dimethoxybenzene
• CAS: 479484-78-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: SEZUWRUZEFZESF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxybenzylcyclopropane 在 三氟乙酸 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 以63%的产率得到5-[(3,4-dimethoxybenzyl)]-4,5-dihydroisoxazole
  参考文献：
  名称：

  Benzyl-4,5-dihydroisoxazoles from benzylcyclo-propanes: regioselective insertion of an n=o fragment into the three-membered carbocycle of benzylcyclopropanes by the action of nitrous acid

  摘要：

  The action of equimolar amounts of nitrous acid formed in situ on benzylcyclopropanes with electron-donor and electron-withdrawing substituents in the aromatic part of the substrate lead, at certain temperatures, exclusively to the insertion of an N=O fragment into the three-membered carbocycle with subsequent formation of a heterocyclic isoxazoline (4,5-dihydroisoxazole) system.

  DOI：

  10.1007/s10593-012-1125-9
• 作为产物：
  描述：

  2-(3,4-dimethoxybenzyl)-1,1-dichlorocyclopropane 在 sodium 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 以73%的产率得到3,4-dimethoxybenzylcyclopropane
  参考文献：
  名称：

  与四氧化二氮反应的环丙基和烯丙基取代的芳烃。底物氧化电位对反应方向的影响

  摘要：

  A correlation was found between oxidation potentials of acylcyclopropanes in solution (in CH2Cl2 and CH3CN) and their HOMO energies calculated by semiempirical (AM1) and nonempirical (HF/6-31G and HF/6-31G**) methods. The correlation provides a possibility to forecast the reaction direction of the mentioned substrates and N2O4. The correlation possesses a general character. It was established for instance that arylcyclopropanes, cyclopropylmethyl- and allylbenzenes oxidized at more positive potentials than reduction potential of NO+ and having more positive epsilon(HOMO) than -9.0 eV (AM1), -8.4 eV (HF/6-31G), and -8.3 eV (HF/6-31 G**) reacted with N2O4 following the mechanism "electron transfer - radical pair recombination" affording nitroaromatic derivatives retaining the cyclopropane (or allyl) fragments. Substrates of the same type where the electron transfer to NO+ should be endothermic process and whose HOMO values are less than the above critical numbers react with N2O4 by the mechanism of electrophilic cyclopropane ring opening (with aryl and benzylcyclopropanes) or by electrophilic addition across the double C=C bond (with allylbenzenes).

  DOI：

  10.1023/b:rujo.0000045888.43245.d7

文献信息

• Fragrance and flavour compositions
  申请人：Givaudan SA

  公开号：EP1269982A1

  公开（公告）日：2003-01-02

  The invention relates to phenyl-cycloalkanes of formula (I) wherein the groups R1 to R6 are defined in the specification.

  该发明涉及公式（I）中的苯基环烷，其中基团R1到R6在说明书中定义。
• FRAGRANCE AND FLAVOUR COMPOSITIONS
  申请人：Givaudan SA

  公开号：EP1401388A2

  公开（公告）日：2004-03-31
• US7704942B2
  申请人：——

  公开号：US7704942B2

  公开（公告）日：2010-04-27
• [EN] FRAGRANCE AND FLAVOUR COMPOSITIONS<br/>[FR] COMPOSITIONS DE PARFUMS ET D'AROMES
  申请人：GIVAUDAN SA

  公开号：WO2003002084A2

  公开（公告）日：2003-01-09

  The invention relates to phenyl-cycloalkanes of formula (I) wherein the groups R1 to R6 are defined in the specification.
• Cyclopropyl- and Allyl-substituted Arenes in Reaction with Dinitrogen Tetroxide. Effect of Substrate Oxidation Potential on Reaction Direction
  作者：S. S. Mochalov、R. A. Gazzaeva、A. N. Fedotov、E. V. Trofimova、I. V. Trushkov、N.S. Zefirov

  DOI：10.1023/b:rujo.0000045888.43245.d7

  日期：2004.8

  A correlation was found between oxidation potentials of acylcyclopropanes in solution (in CH2Cl2 and CH3CN) and their HOMO energies calculated by semiempirical (AM1) and nonempirical (HF/6-31G and HF/6-31G**) methods. The correlation provides a possibility to forecast the reaction direction of the mentioned substrates and N2O4. The correlation possesses a general character. It was established for instance that arylcyclopropanes, cyclopropylmethyl- and allylbenzenes oxidized at more positive potentials than reduction potential of NO+ and having more positive epsilon(HOMO) than -9.0 eV (AM1), -8.4 eV (HF/6-31G), and -8.3 eV (HF/6-31 G**) reacted with N2O4 following the mechanism "electron transfer - radical pair recombination" affording nitroaromatic derivatives retaining the cyclopropane (or allyl) fragments. Substrates of the same type where the electron transfer to NO+ should be endothermic process and whose HOMO values are less than the above critical numbers react with N2O4 by the mechanism of electrophilic cyclopropane ring opening (with aryl and benzylcyclopropanes) or by electrophilic addition across the double C=C bond (with allylbenzenes).