2-Methoxy-4-(prop-1-en-1-yl)-1-[(prop-2-en-1-yl)oxy]benzene | 29653-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Methoxy-4-(prop-1-en-1-yl)-1-[(prop-2-en-1-yl)oxy]benzene
• 英文别名: 2-methoxy-1-prop-2-enoxy-4-prop-1-enylbenzene
• CAS: 29653-02-9
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: KSNCZIFYZXDYSO-UHFFFAOYSA-N

物化性质

• 沸点：
  310.9±27.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  2-Methoxy-4-(prop-1-en-1-yl)-1-[(prop-2-en-1-yl)oxy]benzene 以 neat liquid 为溶剂， 反应 2.0h， 以65%的产率得到
  参考文献：
  名称：

  Boosting effect of ortho- propenyl substituent on the antioxidant activity of natural phenols

  摘要：

  Seven new antioxidants derived from natural or synthetic phenols have been designed as alternatives to BHT and BHA antioxidants. Influence of various substituents at the ortho, meta and para positions of the aromatic core of phenols on the bond dissociation enthalpy of the ArO-H bond was evaluated using a DFT method B3LYP/6-311++G(2d,2p)//B3LYP/6-311G(d,p). This prediction highlighted the ortho-propenyl group as the best substituent to decrease the bond dissociation enthalpy (BDE) value. The rate constants of hydrogen transfer from these phenols to DPPH. radical in a non-polar and non-protic solvent have been measured and were found to be in agreement with the BDE calculations. For o-propenyl derivatives from 2-tert-butyl-4-methylphenol, BHA, creosol, isoeugenol and di-o-propenyl p-cresol, fewer radicals were trapped by a single phenol molecule, i.e. a lower stoichiometric number. Reaction mechanisms involving the evolution of the primary phenoxyl radical ArO are proposed to rationalise these effects. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2015.09.007
• 作为产物：
  描述：

  (E)-2-甲氧基-4-(1-丙烯基苯酚) 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以70%的产率得到2-Methoxy-4-(prop-1-en-1-yl)-1-[(prop-2-en-1-yl)oxy]benzene
  参考文献：
  名称：

  Boosting effect of ortho- propenyl substituent on the antioxidant activity of natural phenols

  摘要：

  Seven new antioxidants derived from natural or synthetic phenols have been designed as alternatives to BHT and BHA antioxidants. Influence of various substituents at the ortho, meta and para positions of the aromatic core of phenols on the bond dissociation enthalpy of the ArO-H bond was evaluated using a DFT method B3LYP/6-311++G(2d,2p)//B3LYP/6-311G(d,p). This prediction highlighted the ortho-propenyl group as the best substituent to decrease the bond dissociation enthalpy (BDE) value. The rate constants of hydrogen transfer from these phenols to DPPH. radical in a non-polar and non-protic solvent have been measured and were found to be in agreement with the BDE calculations. For o-propenyl derivatives from 2-tert-butyl-4-methylphenol, BHA, creosol, isoeugenol and di-o-propenyl p-cresol, fewer radicals were trapped by a single phenol molecule, i.e. a lower stoichiometric number. Reaction mechanisms involving the evolution of the primary phenoxyl radical ArO are proposed to rationalise these effects. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2015.09.007

文献信息

• Thiol/ene compositions
  申请人：LOCTITE (IRELAND) Ltd.

  公开号：EP0229033B1

  公开（公告）日：1993-03-03
• US5021512A
  申请人：——

  公开号：US5021512A

  公开（公告）日：1991-06-04
• [EN] VISIBLE LIGHT CURABLE FREE RADICAL COMPOSITIONS CONTAINING pi -ARENE METAL COMPLEXES
  申请人：LOCTITE CORPORATION

  公开号：WO1988002879A1

  公开（公告）日：1988-04-21

  (EN) A visible light polymerisable composition comprises 1) free radically polymerisable material such as one or more monomers and/or prepolymers containing acrylate or methacrylate groups or a copolymerisable monomer combination based on a polythiol and a polyene. 2) a $i(p)-arene metal complex of formula (I), where a stands for 1 or 2 and n and q independently of each other each stand for an integer from 1 to 3, M is the cation of a monovalent to trivalent metal from groups IVb, VIIb, VIII or Ib of the periodic system, m is an integer corresponding to the valence of L + q, Q is a halogen and L is a metal or nonmetal with a valence of 2 to 7, R1 is a $g(p)-arene and R2 is a $g(p)-arene or the anion of a $g(p)-arene. 3) a free radical rate accelerator such as a peroxide or hydroperoxide compound. More particularly, the $g(p)-arene metal complex is a complex salt of a $g(h)6, $g(h)5 iron arene cation and a non-nucleophilic anion, which is of formula (VII), where R6 is a $g(h)6 arene selected from benzene, alkyl benzenes, alkyloxybenzenes, halobenzenes, haloalkylbenzenes, naphthalene, alkoxynaphthalenes, alkylnaphthalenes, halonaphthalenes, biphenyl, indene, pyrene or diphenylsulphide; R7 is the anion of a cyclopentadienyl compound, L is di- to heptavalent metal or metaloid, Z is a halogen and k is equal to 1 plus the valence of L.(FR) Une composition polymérisable à la lumière visible comprend: 1) un matériau polymérisable à radical libre tel qu'un ou plusieurs monomères et/ou prépolymères contenant des groupes acrylates ou méthacrylates ou une combinaison monomère copolymérisable basée sur un polythyol ou un polyène; 2) un complexe métallique $g(p)-arène de formule (I) dans laquelle a représente 1 ou 2 et n et q, indépendamment l'un de l'autre, représentent un nombre entier compris entre 1 et 3, M représente le cathium d'un métal monovalent à trivalent parmi les groupes IVb, VIIb, VIII ou Ib du système périodique, m est un nombre entier correspondant à la valence de L + q, Q représente un halogène et L est un métal ou un non métal, avec une valence comprise entre 2 et 7, R1 représente $g(p)-arène et R2 représente $g(p)-arène ou bien l'anion de $g(p)-arène. 3) un accélérateur à radical libre tel qu'un composé pyroxide ou hydropyroxyde. Plus particulièrement, le complexe métallique $g(p)-arène est un sel complexe $g(h)6, $g(h)5 d'un cation d'arène de fer et un anion non nucléophyle de formule (VII) dans laquelle R6 reprrésente $g(h)6 arène sélectionné parmi le benzène, des alkylbenzènes, des alkyloxybenzènes, des halobenzènes, des haloalkylbenzènes, du naphtalène, des alcoxynaphthalènes, des alkylnaphtalènes, des halonaphtalènes, le biphényle, l'indène, le pyrène ou le diphénylsulfure; R7 représente l'anion d'un composé cyclopentadiényle, L représente un métaloïde ou un métal bivalent à heptavalent, Z est un halogène et k est égal à 1 plus la valence de L.
• Boosting effect of ortho- propenyl substituent on the antioxidant activity of natural phenols
  作者：Clémentine Marteau、Romain Guitard、Christophe Penverne、Dominique Favier、Véronique Nardello-Rataj、Jean-Marie Aubry

  DOI：10.1016/j.foodchem.2015.09.007

  日期：2016.4

  Seven new antioxidants derived from natural or synthetic phenols have been designed as alternatives to BHT and BHA antioxidants. Influence of various substituents at the ortho, meta and para positions of the aromatic core of phenols on the bond dissociation enthalpy of the ArO-H bond was evaluated using a DFT method B3LYP/6-311++G(2d,2p)//B3LYP/6-311G(d,p). This prediction highlighted the ortho-propenyl group as the best substituent to decrease the bond dissociation enthalpy (BDE) value. The rate constants of hydrogen transfer from these phenols to DPPH. radical in a non-polar and non-protic solvent have been measured and were found to be in agreement with the BDE calculations. For o-propenyl derivatives from 2-tert-butyl-4-methylphenol, BHA, creosol, isoeugenol and di-o-propenyl p-cresol, fewer radicals were trapped by a single phenol molecule, i.e. a lower stoichiometric number. Reaction mechanisms involving the evolution of the primary phenoxyl radical ArO are proposed to rationalise these effects. (C) 2015 Elsevier Ltd. All rights reserved.