O-(4-methylbenzyl)hydroquinone | 54589-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: O-(4-methylbenzyl)hydroquinone
• 英文别名: 4-(4-methylbenzyloxy)phenol；Phenol, 4-[(4-methylphenyl)methoxy]-；4-[(4-methylphenyl)methoxy]phenol
• CAS: 54589-51-4
• 化学式: C₁₄H₁₄O₂
• mdl: MFCD11181730
• 分子量: 214.264
• InChiKey: NWCZJELJQHRHOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  154.5-155.5 °C
• 沸点：
  373.1±22.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-(4-methylbenzyl)hydroquinone 在 吡啶 、 水 、 potassium carbonate 、 caesium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.0h， 生成 (1-benzyl-5-{3-[4-(4-methylbenzyloxy)phenoxy]propoxy}-1H-indol-3-yl)acetic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a series of alkoxy-3-indolylacetic acids as peroxisome proliferator-activated receptor γ/δ agonists

  摘要：

  A series of alkoxy-3-indolylacetic acid analogs has been discovered as peroxisome proliferator-activated receptor (PPAR) agonists. Structure-activity relationship study indicated that PPAR alpha/gamma/delta activities were dependent on the nature of the hydrophobic group, the attachment position of the alkoxy linker to the indole ring, and N-alkylation of indole nitrogen. Some compounds presented significant PPAR gamma/delta activity and molecular modeling suggested their putative binding modes in the ligand binding domain of PPAR gamma. Of these, compound 51 was selected for in vivo study via an evaluation of microsomal stability in mouse and human liver. Compound 51 lowered the levels of fasting blood glucose, insulin, and HbA1c without gain in body weight in db/db mice. When compound 51 was treated, hepatic triglycerides level and the size of adipocytes in white adipose tissue of db/db mice were also reduced as opposed to treatment with rosiglitazone. Taken together, compound 51 shows high potential warranting further studies in models for diabetes and related metabolic disorders and may be in use as a chemical tool for the understanding of PPAR biology. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.046
• 作为产物：
  描述：

  1-benzyloxy-4-(4-methylbenzyloxy)benzene 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 O-(4-methylbenzyl)hydroquinone
  参考文献：
  名称：

  Pd/C-Catalyzed Chemoselective Hydrogenation in the Presence of a Phenolic MPM Protective Group Using Pyridine as a Catalyst Poison.

  摘要：

  使用Pd/C-吡啶组合作为催化剂是一种非常有用的方法，用于选择性地去除（氢解）酚类化合物的O-苄基、N-Cbz和苄基酯保护基团，以及选择性地氢化带有MPM保护基团的酚类衍生物中的硝基和烯烃功能团。这些差异性结果显然归因于吡啶的作用。MPM基团可广泛应用于作为酚羟基功能团的选择性氢化保护基。

  DOI：

  10.1248/cpb.51.320

文献信息

• Thermotropic liquid crystalline polyesters
  申请人：Montedison S.p.A.

  公开号：EP0300752A2

  公开（公告）日：1989-01-25

  Thermotropic liquid crystalline polyesters which can be processed in the molten state containing moieties derived from a dicarboxylic aromatic acid and 2,5-dihydroxybenzophenone optionally in a mixture with a substituted hydroquinone.

  可在熔融状态下加工的热致性液晶聚酯，含有二羧基芳香族酸和 2,5-二羟基二苯甲酮（可选择与取代的对苯二酚混合）的分子。
• Citterio, Attilio, Gazzetta Chimica Italiana, 1980, vol. 110, # 4, p. 253 - 258
  作者：Citterio, Attilio

  DOI：——

  日期：——
• US4952661A
  申请人：——

  公开号：US4952661A

  公开（公告）日：1990-08-28
• US7534547B2
  申请人：——

  公开号：US7534547B2

  公开（公告）日：2009-05-19
• Pd/C-Catalyzed Chemoselective Hydrogenation in the Presence of a Phenolic MPM Protective Group Using Pyridine as a Catalyst Poison.
  作者：Hironao Sajiki、Kosaku Hirota

  DOI：10.1248/cpb.51.320

  日期：——

  Employment of a Pd/C–pyridine combination as a catalyst is a very useful method for the selective removal (hydrogenolysis) of phenolic O-benzyl, N-Cbz and benzyl ester protective groups and for the selective hydrogenation of nitro and olefin functions of phenol derivatives protected with the MPM group. These discriminatory results are apparently attributable to the effect of pyridine. The MPM group could be extensively applied to chemoselective hydrogenation as a protective group for phenolic hydroxyl functions.

  使用Pd/C-吡啶组合作为催化剂是一种非常有用的方法，用于选择性地去除（氢解）酚类化合物的O-苄基、N-Cbz和苄基酯保护基团，以及选择性地氢化带有MPM保护基团的酚类衍生物中的硝基和烯烃功能团。这些差异性结果显然归因于吡啶的作用。MPM基团可广泛应用于作为酚羟基功能团的选择性氢化保护基。