双(2,5-二甲氧基-4-甲基苯基)甲烷 | 3948-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 双(2,5-二甲氧基-4-甲基苯基)甲烷
• 英文名称: bis(2,5-dimethoxy-4-methylphenyl)methane
• 英文别名: Bis-(2,5-dimethoxy-4-methyl-phenyl)-methan；1-[(2,5-Dimethoxy-4-methylphenyl)methyl]-2,5-dimethoxy-4-methylbenzene
• CAS: 3948-92-3
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: ZYSPSAUYZWVCEK-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  433.7±40.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  双(2,5-二甲氧基-4-甲基苯基)甲烷 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 生成 1-(氯甲基)-2,5-二甲氧基-4-甲基苯 、 2-Chloro-5-methyl-1,4-dimethoxybenzene
  参考文献：
  名称：

  Radical-Cation Catalysis in the Synthesis of Diphenylmethanes via the Dealkylative Coupling of Benzylic Ethers

  摘要：

  The dealkylative coupling of benzyl alkyl ethers (ArCH(2)OR) to yield the corresponding diarylmethanes (ArCH2Ar) together with dialkoxymethane (ROCH(2)OR) is catalyzed by small amounts of 1-electron oxidants (such as aromatic cation radicals, NO+, etc.) or py an equivalent electrochemical (anodic) method. The catalytic method is successfully employed for the facile synthesis of a novel macrocyclic crown ether 18 that contains a diarylmethane linkage. On the basis of the spectral observation of the radical cation ArCH(2)OR(.+) and the excellent catalytic efficiency with turnover numbers in excess of 10(2), an electron-transfer and an alternative electrophilic chain mechanism are discussed for the dealkylative coupling process.

  DOI：

  10.1021/jo00128a020
• 作为产物：
  描述：

  1,4-二(溴甲基)-2,5-二甲氧基苯 在 Orange CRET^.+ 、 锌 作用下， 以 甲醇 为溶剂， 反应 8.08h， 生成 双(2,5-二甲氧基-4-甲基苯基)甲烷
  参考文献：
  名称：

  Radical-Cation Catalysis in the Synthesis of Diphenylmethanes via the Dealkylative Coupling of Benzylic Ethers

  摘要：

  The dealkylative coupling of benzyl alkyl ethers (ArCH(2)OR) to yield the corresponding diarylmethanes (ArCH2Ar) together with dialkoxymethane (ROCH(2)OR) is catalyzed by small amounts of 1-electron oxidants (such as aromatic cation radicals, NO+, etc.) or py an equivalent electrochemical (anodic) method. The catalytic method is successfully employed for the facile synthesis of a novel macrocyclic crown ether 18 that contains a diarylmethane linkage. On the basis of the spectral observation of the radical cation ArCH(2)OR(.+) and the excellent catalytic efficiency with turnover numbers in excess of 10(2), an electron-transfer and an alternative electrophilic chain mechanism are discussed for the dealkylative coupling process.

  DOI：

  10.1021/jo00128a020

文献信息

• Transpositions d'hydroxy-diquinones I. Pr�paration de l'hydroxy-2-dim�thyl-4,4? -diquinone-3,6,3?,6? et du penta-hydroxy-2,3,6,3?,6?-dim�thoxy-4,4? -diph�nyle
  作者：Th. Posternak、W. Alcalay、R. Huguenin

  DOI：10.1002/hlca.19560390614

  日期：——

  Les préparations de l'hydroxy-2-diméthyl-4,4′-diquinone-3,6,3′,(XIV) et du penta-hydroxy-2,3,6,3′, 6′-dimythoxy-4,4′-diphényle (XXVIII) ont été décrites.

  羟基-二羟基-4,4'-二醌-3,6,3'，（XIV）等五羟基-2,3,6,3'，6'-二甲氧基-4， 4'-diphényle（XXVIII）ontétédécrites。
• Acid Catalysis vs. Electron-Transfer Catalysis via Organic Cations or Cation-Radicals as the Reactive Intermediate. Are These Distinctive Mechanisms?
  作者：Rajendra Rathore、Jay K. Kochi、Augusto Canavesi、Larry L. Miller、Giovanni V. Sebastiani、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0114

  日期：——

  Proton transfer to aromatic and olefinic donors (D) lends to the facile interchange of transient carbocations (DH+) and cation-radical (D+.). The same types of cation and cation-radical are reactive intermediates in the acid catalysis and the electron-transfer catalysis of such organic transformations as benzylic coupling, epoxide.-pinacol rearrangements and cis-trans isomerization of stilbenes when they are both carried out under otherwise identical reaction conditions, However, the rapid exchange of diamagnetic cations and paramagnetic cation-radicals blurs the traditional view of sepal ate electrophilic and homolytic processes, and rigorous experimental evidence is required to establish whether acid catalysis and electron-transfer catalysis actually represent distinct mechanistic categories.
• Jacini; Bacchetti, Gazzetta Chimica Italiana, 1950, vol. 80, p. 757,760
  作者：Jacini、Bacchetti

  DOI：——

  日期：——
• Bis(2,5-dimethoxy-4-methylphenyl)methane and bis(2,5-dimethoxy-3,4,6-trimethylphenyl)methane
  作者：David J. Wiedenfeld、Vladimir N. Nesterov、Mark A. Minton、David R. Glass

  DOI：10.1107/s0108270103024673

  日期：2003.12.15

  Bis(2,5-dimethoxy-4-methylphenyl) methane, C19H24O4, (IIa), was obtained and characterized as a minor product from the reaction of toluhydroquinone dimethyl ether (1,4-dimethoxy-2- methylbenzene) with N-(hydroxymethyl) trifluoroacetamide. Similarly, bis(2,5-dimethoxy-3,4,6-trimethylphenyl) methane, C23H32O4, (IIb), was prepared from the corresponding reaction of trimethylhydroquinone dimethyl ether (2,5-dimethoxy- 1,3,4-trimethylbenzene). The molecules of ( IIa) and (IIb) each lie on a twofold axis passing through the methylene group. The dihedral angle between the planar phenyl rings is 73.4 (1)degrees in (IIa) and 77.9 (1)degrees in (IIb). The external bond angles around the bridging methylene group are 116.6 (2) and 117.3 (2)degrees for (IIa) and (IIb), respectively. In (IIa), the methoxy substituents lie in the plane of the ring and are conjugated with the aromatic system, whereas in (IIb), they are almost perpendicular to the phenyl ring and are positioned on opposite sides.
• LEWIN A. H.; PARKER S. R.; FLEMING N. B.; CARROLL F. I., ORG. PREP. AND PROCED. INT., 1978, 10, NO 5, 201-204
  作者：LEWIN A. H.、 PARKER S. R.、 FLEMING N. B.、 CARROLL F. I.

  DOI：——

  日期：——