p-Dimethoxybenzol-2-d | 72617-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: p-Dimethoxybenzol-2-d
• 英文别名: 2-deuterio-1,4-dimethoxy-benzene；2-deuterio-1,4-dimethoxybenzene
• CAS: 72617-62-0
• 化学式: C₈H₁₀O₂
• 分子量: 139.158
• InChiKey: OHBQPCCCRFSCAX-WFVSFCRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对苯二甲醚 在 四氢呋喃 、 sodium diisopropylamide 、 氘代甲醇-d 作用下， 生成 p-Dimethoxybenzol-2-d
  参考文献：
  名称：

  四氢呋喃中的二异丙基氨基钠：选择性，速率和芳烃金属化的机制。

  摘要：

  描述了在四氢呋喃（THF）/己烷或THF / Me 2 NEt溶液中，二异丙基氨基钠（NaDA）介导的芳烃金属化。对超过40种具有一系列取代基的基于苯并吡啶和吡啶的芳烃的研究表明，其金属化的功效和区域选择性都很高。活化的二取代的芳烃和选定的单取代的芳烃在-78°C时快速金属化。1,3-二甲氧基苯和相关甲氧基化芳烃的速率研究表明，基于单体的原金属具有两个或三个配位的THF配体。苯和具有弱活化基团的单取代芳烃的同位素交换速率研究表明，类似的二溶剂化和三溶剂化的单体基金属化反应。讨论了协同的诱导，消旋，空间和螯合作用。

  DOI：

  10.1021/jacs.7b08734

文献信息

• Photochemistry of dimethoxybenzenes in aqueous sulfuric acid
  作者：Renee Pollard、Susan Wu、Guangzhong Zhang、Peter Wan

  DOI：10.1021/jo00061a042

  日期：1993.4

  The photochemistry of the three isomeric dimethoxybenzenes (1-3) has been studied in aqueous sulfuric acid. Two processes were found to take place: (i) photoprotonation of the ring resulting in exchange of the ring protons, which was observed for all three compounds and (ii) ipso substitution of the methoxy group by water, which was observed only for 1,2-dimethoxybenzene (3). Both of these photochemical reactions were catalyzed by acid, requiring acidities stronger than pH(D) 2 for observable reaction. Quantum yields for proton exchange and ipso substitution are reported as a function of medium acidity. The fluorescence emissions of all three compounds were quenched by acid, to give sigmoid type quenching curves, that have a complementary relationship with the corresponding plots of quantum yield of exchange vs acidity, consistent with protonation of the benzene ring in S1 as the primary photochemical step, to give cyclohexadienyl cation intermediates. Stern-Volmer analysis of fluorescence quenching by proton gave photoprotonation rates in the range 0.09-2.2 X 10(9) M-1 s-1. The results of this work demonstrate unambiguously that methoxy-substituted benzenes are much stronger bases in S1 (pK(BH)+ congruent-to 1 to -2) than in the ground state. This enhanced basicity is manifested in regioselectivity of exchange of 1 and 3 and ipso substitution chemistry of 3, processes not observed in the ground states of these compounds.
• WAN, PETER;WU, PIN, J. CHEM. SOC. CHEM. COMMUN.,(1990) N1, C. 822-823
  作者：WAN, PETER、WU, PIN

  DOI：——

  日期：——