3-(4-methoxy-1-naphthalenyl)propan-1-ol | 79623-18-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(4-methoxy-1-naphthalenyl)propan-1-ol
• 英文别名: 3-(4-Methoxynaphthalen-1-yl)propan-1-ol
• CAS: 79623-18-0
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: ZLJNOVFBNAEGOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  3-(4-methoxy-1-naphthalenyl)propan-1-ol 在 5%-palladium/activated carbon 、 水 、 氢气 、 sodium hydride 、 pyridinium chlorochromate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 5-(4-methoxynaphthalen-1-yl)pentanoic acid
  参考文献：
  名称：

  Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid

  摘要：

  The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.080

文献信息

• Nucleophilic attack of intramolecular hydroxyl groups on electron-rich aromatics using hypervalent iodine(III) oxidation
  作者：Kayoko Hata、Hiromi Hamamoto、Yukiko Shiozaki、Simon B. Cämmerer、Yasuyuki Kita

  DOI：10.1016/j.tet.2007.02.118

  日期：2007.5

  The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA)-mediated oxidative nucleophilic substitution of electron-rich aromatics involving aromatic cation radical intermediates was utilized in the direct aromatic carbon–oxygen bond formation reaction, and a novel and simple synthetic method for chroman derivatives was developed. As an extension of this methodology, a facile access

  高价碘试剂（IIIFA），苯碘酸双（三氟乙酸盐）（PIFA）介导的涉及芳香族阳离子自由基中间体的富电子芳族化合物的氧化亲核取代反应被用于直接的芳族碳-氧键形成反应中，以及一种新颖而简单的合成方法开发了苯并二氢吡喃衍生物的方法。作为该方法的扩展，还可以轻松获得螺二烯酮衍生物。
• Thallium in organic synthesis. 61. Intramolecular capture of radical cations from thallium(III) trifluoroacetate oxidation of arylalkanoic acids and arylalkanols. New routes to oxygen heterocycles
  作者：Edward C. Taylor、Juan G. Andrade、Gerhardus J. H. Rall、Ignatius J. Turchi、Kosta Steliou、G. Erik Jagdmann、Alexander McKillop

  DOI：10.1021/ja00413a013

  日期：1981.11
• Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid
  作者：Seisuke Mimori、Yukari Koshikawa、Yu Mashima、Katsuyoshi Mitsunaga、Koichi Kawada、Masayuki Kaneko、Yasunobu Okuma、Yasuyuki Nomura、Yasuoki Murakami、Tetsuto Kanzaki、Hiroshi Hamana

  DOI：10.1016/j.bmcl.2014.12.080

  日期：2015.2

  The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene. (C) 2015 Elsevier Ltd. All rights reserved.