3-Hydroxy-1,4-dimethyl-2-naphthalenecarboxylic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Hydroxy-1,4-dimethyl-2-naphthalenecarboxylic acid
• 英文别名: 3-Hydroxy-1,4-dimethylnaphthalene-2-carboxylic acid；3-hydroxy-1,4-dimethylnaphthalene-2-carboxylic acid
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: QKHPGLRCRNWULP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-dihydro-1,4-dimethyl-1,4-epoxynaphthalene 在 氢氧化钾 、 C.I.酸性橙108 、 copper(l) chloride 、 叔丁醇 作用下， 反应 26.0h， 生成 3-Hydroxy-1,4-dimethyl-2-naphthalenecarboxylic acid
  参考文献：
  名称：

  Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to α,β-unsaturated carboxylates

  摘要：

  Alternative mechanisms for the title reactions are probed. The previously-reported pathway involving double dehydrobromination to a difluorodiene is operative in at least one case, but this route is specifically excluded for systems that cannot dehydrobrominate to dienes yet still yield carboxylates upon alkaline hydrolysis. Although S(N)2, S(N)1, S(RN)1, and monoelimination-addition processes appear formally possible, an S(N)2' mechanism is implicated by studies on model compounds. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00232-8

文献信息

• Mechanisms for the alkaline hydrolysis of dibromodifluoromethane-alkene adducts to α,β-unsaturated carboxylates
  作者：Seth Elsheimer、JoAnne L. Swanson、Javier Gonzalez

  DOI：10.1016/s0022-1139(99)00232-8

  日期：2000.3

  Alternative mechanisms for the title reactions are probed. The previously-reported pathway involving double dehydrobromination to a difluorodiene is operative in at least one case, but this route is specifically excluded for systems that cannot dehydrobrominate to dienes yet still yield carboxylates upon alkaline hydrolysis. Although S(N)2, S(N)1, S(RN)1, and monoelimination-addition processes appear formally possible, an S(N)2' mechanism is implicated by studies on model compounds. (C) 2000 Elsevier Science S.A. All rights reserved.