2-[2-(羟甲基)苯基]苯酚 | 3594-97-6

• 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: 2-[2-(羟甲基)苯基]苯酚
• 英文名称: 2-(2'-hydroxyphenyl)benzyl alcohol
• 英文别名: 2-(2-Hydroxymethylphenyl)phenol；2-[2-(hydroxymethyl)phenyl]phenol
• CAS: 3594-97-6
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: FGCSCCNLDZVFBI-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C(Solv: ethanol (64-17-5))
• 沸点：
  387.0±30.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-(羟甲基)苯基]苯酚 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 生成 2-甲基-2'-羟基联苯
  参考文献：
  名称：

  联芳系统光生醌甲基化物的溶剂分解和闭环

  摘要：

  各种联芳基醌甲基化物已经从联芳基前体 4??6 和 8、10 和 11 以一系列效率光生，它们都具有交替的羟基和羟甲基取代基。

  DOI：

  10.1139/v05-138
• 作为产物：
  描述：

  苯并[c]苯并吡喃-6-酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以94%的产率得到2-[2-(羟甲基)苯基]苯酚
  参考文献：
  名称：

  [biphen(QPiPr)Pt(alk)2] 热分解的研究：进入 C-C 单键活化？

  摘要：

  [(COD)PtCl2] 与联苯 (QPiPr)(Q'PiPr) (Q, Q' = O, CH2O) 反应生成顺式-[{biphen(QPiPr)(Q'PiPr)}PtCl2]。用联苯(QPiPr)(Q'PiPr) (Q, Q' = O, CH2O)处理反式-[PtCl2(乙烯)(py)]得到反式-[{biphen(QPiPr)(Q'PiPr)}PtCl2]对于 Q 或 Q' ≠ O。这些化合物在 [D8] 甲苯中 105 °C 下 24 小时后未观察到反式/顺式异构化。在 Q = Q' = O 的情况下，反式/顺式异构化在室温下发生。对于化合物 cis/trans-[{biphen(QPiPr)(Q'PiPr)}PtCl2]，其中 Q 或 Q'≠O，确定了固态分子的 X 射线结构。在 Q = O 的情况下， Q' = CH2O 配体的联苯片段中两个桥接 C 原子中较近的距离 Pt 中心仅

  DOI：

  10.1002/ejic.200600848

文献信息

• Diastereoselective Remote CH Activation by Hydroboration
  作者：Jesús A. Varela、Diego Peña、Bernd Goldfuss、Dmitri Denisenko、Jiri Kulhanek、Kurt Polborn、Paul Knochel

  DOI：10.1002/chem.200400023

  日期：2004.9.6

  thermolysis allows remote diastereoselective C-H activation of neighboring aryl rings. Tetrasubstituted and trisubstituted 1,1-diphenylethylene derivatives undergo a highly stereoselective 1,2-rearrangement followed by remote C-H activation to lead, after oxidative workup, to a diol in which the relative stereochemistry of two stereocenters has been controlled. The mechanism of this remote activation has been

  四取代或三取代的烯烃与BH（3）的氢硼化以及随后的热分解反应使邻近的芳基环可以进行非对映选择性的CH活化。四取代和三取代的1,1-二苯基乙烯衍生物经过高度立体选择性的1,2-重排，然后经远程CH活化，在氧化处理后导致形成可控制两个立构中心的相对立构化学的二醇。已经研究了这种远程活化的机理，并将其扩展到经历了这种立体选择性CH活化的相关分子，即烯基联苯系统或仅具有一个苯环的烯烃，例如烯基苯或双环系统。我们已经表明，该反应允许具有多达三个连续手性中心的分子的非对映选择性合成。
• DERIVATIVES OF 6-SUBSTITUTED TRIAZOLOPYRIDAZINES AS REV-ERB AGONISTS
  申请人：GENFIT

  公开号：US20150038503A1

  公开（公告）日：2015-02-05

  The present invention provides novel 6-substituted [1,2,4]triazolo[4,3-b]pyridazines that are agonists of Rev-Erb. These compounds, and pharmaceutical compositions comprising the same, are suitable means for treating any disease wherein the activation of Rev-Erb has therapeutic effects, for instance in inflammatory and circadian rhythm-related disorders or cardiometabolic diseases.

  本发明提供了新型的6-取代[1,2,4]三唑并[4,3-b]吡啶嗪，这些化合物是Rev-Erb激动剂。这些化合物及其含有的药物组合物是治疗任何需要Rev-Erb激活具有治疗效果的疾病的适当手段，例如炎症和昼夜节律相关疾病或心脏代谢疾病。
• Derivatives of 6-substituted triazolopyridazines as Rev-Erb agonists
  申请人：GENFIT

  公开号：US10799510B2

  公开（公告）日：2020-10-13

  The present invention provides novel 6-substituted [1,2,4]triazolo[4,3-b]pyridazines that are agonists of Rev-Erb. These compounds, and pharmaceutical compositions comprising the same, are suitable means for treating any disease wherein the activation of Rev-Erb has therapeutic effects, for instance in inflammatory and circadian rhythm-related disorders or cardiometabolic diseases.

  本发明提供了新型 6-取代的[1,2,4]三唑并[4,3-b]哒嗪，它们是 Rev-Erb 的激动剂。这些化合物以及包含这些化合物的药物组合物适用于治疗任何激活 Rev-Erb 具有治疗效果的疾病，例如炎症和昼夜节律相关疾病或心脏代谢疾病。
• Mechanism of photoisomerization of xanthene to 6H-dibenzo[b,d]pyran in aqueous solution
  作者：C. G. Huang、Deepak Shukla、Peter Wan

  DOI：10.1021/jo00018a044

  日期：1991.8

  A new photoreaction, the photoisomerization of xanthene (1) to 6H-dibenzo[b,d]pyran (2) (almost-equal-to 70%) (PHI = 0.0035 in 7:3 H2O-CH3CN) in aqueous CH3CN solution is reported. In addition to 2, 2-benzylphenol (3) (PHI almost-equal-to 0.001), 9,9'-bixanthyl (4) (PHI < 0.001), and 2-(2'-hydroxyphenyl)benzyl alcohol (5) (PHI < 0.001) are also observed as minor products. 9-Methylxanthene (9) also photoisomerizes to the corresponding pyran derivative 10, although in this case much lower yields are observed due to secondary photochemistry of 10. The photoisomerization of 1 is most efficient in aqueous solution: PHI increased with increasing water content in a H2O-CH3CN solvent mixture. A mechanism of photoisomerization is proposed that involves initial Ar-O bond homolysis from S1, to generate a singlet biradical. Trivial recombination gives back unreacted 1. Hydrogen abstraction from solvent leads to the photoreduction product 3. However, recombination of the biradical at the ipso benzylic position (ortho to phenol) gives a cyclohexadienone intermediate 17. Subsequent transformation of this species to 2 occurs via an o-quinone methide intermediate 18, which itself can be trapped with MeOH or H2O, to give the corresponding methyl ether derivative 8 or alcohol 5.
• Photochemistry of phenoxybenzyl alcohols in aqueous solution: photosolvolysis vs. photorearrangement to 6H-dibenzo[b,d]pyrans
  作者：C. G. Huang、Peter Wan

  DOI：10.1021/jo00016a009

  日期：1991.8

  The photochemistry of three phenoxybenzyl alcohols (1-3) has been studied in MeOH, CH3CN, and in aqueous solution. It was found that both of the ortho-substituted phenoxybenzyl alcohols 1 and 2 gave the corresponding 6H-dibenzo[b,d]pyrans 6 and 10, via a mechanism believed to involve initial aryl C-O bond homolysis followed by rearrangement to give a 2-(2'-hydroxyphenyl)benzyl alcohol (biphenyl) derivative, which subsequently undergoes a photocyclization reaction to the corresponding 6H-dibenzo[b,d]pyran. The quantum yield for formation of 6 (from 1) was 0.0073 in neutral 6:4 H2O-CH3CN. Lower quantum yields for formation of 6 were observed on photolysis in pure organic solvents (PHI = 0.0015 in 100% CH3CN). The meta-substituted isomer 3 did not give any reaction via a similar photocyclization process: its photochemistry involves initial aryl C-O bond homolysis followed by simple radical recoupling to give isomeric hydroxybiphenyls, as well as products derived from radical escape. In aqueous sulfuric acid solution (pH < 2), a competing acid-catalyzed photosolvolysis reaction was observed for all of these compounds (i.e., C-OH bond heterolysis with assistance of hydronium ion); it was the only observed reaction in moderately concentrated sulfuric acid solution.