8-羟基-1-萘甲醛 | 35689-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 8-羟基-1-萘甲醛
• 英文名称: 8-hydroxy-1-naphthaldehyde
• 英文别名: 8-hydroxynaphthalene-1-carbaldehyde
• CAS: 35689-26-0
• 化学式: C₁₁H₈O₂
• 分子量: 172.183
• InChiKey: ZEUYQHCPNSUTRG-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C(Solv: ethanol, 95% (64-17-5))
• 沸点：
  373.4±15.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  8-羟基-1-萘甲醛 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 barium dihydroxide 、 zinc diacetate 、 丙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 90.75h， 生成 5-(8-(5-indanyl)naphth-1-yl)-10,15,20-triphenylporphyrinato zinc
  参考文献：
  名称：

  Cofacial Porphyrin−Ferrocene Dyads and a New Class of Conjugated Porphyrin

  摘要：

  [GRAPHIC]A porphyrin-ferrocene dyad has been synthesized in which there is close face-to-face contact between the two aromatic systems, providing a model for heterobimetallic polymers based on the same repeating unit. Attempts to synthesize the 2:1 adduct instead led to a remarkable intramolecular Heck-type cyclization which planarizes the system and extends the conjugation.

  DOI：

  10.1021/ol050962g
• 作为产物：
  描述：

  1-甲氧基萘 在 三氯化铝 作用下， 生成 8-羟基-1-萘甲醛
  参考文献：
  名称：

  锂化反应的合成应用-VII：线性和有角萘呋喃和苯并香豆素的新合成

  摘要：

  使用锂化反应，已经合成了四种甲氧基和羟基萘醛。其中三个已被转化为相应的萘呋喃和苯并香豆素。

  DOI：

  10.1016/0040-4020(75)80118-9

文献信息

• Palladium‐Catalyzed C8‐Oxygenation of Naphthalene Derivatives: Direct Access to Naphtholactone Skeleton
  作者：Caroline Berrou、Sébastien Prévost

  DOI：10.1002/adsc.202100317

  日期：2021.8.13

  Herein, a direct C8-oxygenation of naphthalene derivatives is described. Different carbonyl groups were used as directing group to deliver corresponding naphthols via a palladium-catalyzed oxidation reaction using PhI(OAc)2 in a TFA/TFAA mixture. Interestingly, when Weinreb amide was employed as the directing group, the naphtholactone skeleton was directly obtained. This methodology was applied to

  在此，描述了萘衍生物的直接 C8-氧化。使用不同的羰基作为导向基团，通过钯催化的氧化反应，在 TFA/TFAA 混合物中使用 PhI(OAc) 2来递送相应的萘酚。有趣的是，当采用 Weinreb 酰胺作为导向基团时，直接获得了萘内酯骨架。该方法用于合成各种取代的萘内酯。
• Anionic ortho-Fries Rearrangement, a Facile Route to Arenol-Based Mannich Bases
  作者：Petros Tsoungas、Nikos Assimomytis、Yiannis Sariyannis、Georgios Stavropoulos、George Varvounis、Paul Cordopatis

  DOI：10.1055/s-0029-1217991

  日期：2009.10

  and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90 °C, un- der a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-((dialkylami- no)methyl)-8-hydroxy-1-naphthaldehydes

  苯酚和基于 1-萘酚的氨基甲酸酯经过阴离子邻位-弗里斯重排为其相应的酰胺。1-萘酚基氨基甲酸酯在 8 位的大量取代使重排成为一种独特的反应，即使在 -90 °C 下，在各种条件下也是如此。酰胺可以有效地还原为相应的曼尼希碱。提出了一种制备 7-((二烷基氨基) 甲基)-8-羟基-1-萘醛的新途径。
• Synthesis, In vitro α-Glucosidase Inhibitory Potential and Molecular Docking Studies of 2-Amino-1,3,4-Oxadiazole Derivatives
  作者：Hayat Ullah、Fazal Rahim、Muhammad Taha、Raffaqat Hussain、Abdul Wadood、Mohsan Nawaz、Zainul Wahab、Kanwal、Khalid M. Khan

  DOI：10.2174/1573406415666190612150447

  日期：2020.9.7

  In the recent past, we have synthesized and reported different derivatives of oxadiazoles as potential α-glucosidase inhibitors, keeping in mind, the pharmacological aspects of oxadiazole moiety and in continuation of our ongoing research on the chemistry and bioactivity of new heterocyclic compounds.

  1,3,4-Oxadiazole derivatives (1-14) have been synthesized and characterized by different spectroscopic techniques such as 1H-, 13C-NMR and HREI-MS.

  The synthetic derivatives were screened for α-glucosidase inhibitory potential. All compounds exhibited good inhibitory activity with IC50 values ranging between 0.80 ± 0.1 to 45.1 ± 1.7 μM in comparison with the standard acarbose having IC50 value 38.45 ± 0.80 μM.

  Thirteen compounds 1-6 and 8-14 showed potential inhibitory activity as compared to the standard acarbose having IC50 value 38.45 ± 0.80 μM, however, only one compound 7 (IC50 = 45.1 ± 1.7 μM) was found to be less active. Compound 14 (IC50 = 0.80 ± 0.1 μM) showed promising inhibitory activity among all synthetic derivatives. Molecular docking studies were also conducted for the active compounds to understand the ligand-enzyme binding interactions.

  背景：最近，我们合成并报告了不同的氧代二唑衍生物作为潜在的α-葡萄糖苷酶抑制剂，考虑到氧代二唑基团的药理学方面，并延续我们对新异环化合物的化学和生物活性研究。 方法：合成和表征了1,3,4-氧代二唑衍生物（1-14），并通过不同的光谱技术如1H-、13C-NMR和HREI-MS进行了表征。 结果：合成的衍生物被筛选用于α-葡萄糖苷酶抑制潜力。所有化合物在抑制活性方面表现出良好的活性，IC50值在0.80±0.1至45.1±1.7μM之间，与标准药物阿卡波糖的IC50值38.45±0.80μM相比。 结论：化合物1-6和8-14中的十三种化合物显示出潜在的抑制活性，与具有IC50值38.45±0.80μM的标准药物阿卡波糖相比，然而，只有一种化合物7（IC50=45.1±1.7μM）显示出较低的活性。化合物14（IC50=0.80±0.1μM）在所有合成衍生物中表现出有希望的抑制活性。还进行了活性化合物的分子对接研究，以了解配体-酶结合相互作用。
• [EN] INHIBITORS OF KRAS G12C<br/>[FR] INHIBITEURS DE KRAS G12C
  申请人：BEIGENE LTD

  公开号：WO2021058018A1

  公开（公告）日：2021-04-01

  Disclosed herein are compounds that inhibit KRas G12C, pharmaceutical compositions, methods of preparation and uses thereof.

  本文揭示了一些抑制KRas G12C的化合物，包括制备方法、药物组合物以及使用方法。
• Attractive and repulsive effects in the interactions between electron-rich and electron-deficient groups in peri-substituted naphthalenes
  作者：Jane O’Leary、Paul C. Bell、John D. Wallis、W. Bernd Schweizer

  DOI：10.1039/b008226k

  日期：——

  accord with the different nucleophilicities of the two groups. These separations are a balance between a steric effect and a covalent interaction, and from a comparison of the Me2N⋯C and MeO⋯C distances for a given functional group it is proposed that the Me2N⋯C interaction has an attractive component if the Me2N⋯C separation is less than ∼(MeO⋯C + 0.15) Å, the latter factor arising from the greater size

  一系列周边取代的1,5 Me 2 N ⋯ C（sp 2）分离萘衍生物对含碳官能团的全空间电子吸引能力敏感，而相应的MeO ⋯ C（sp 2）分离对这两个基团的不同亲核性则相对不敏感。这些分离是空间效应和共价相互作用之间的平衡，并且通过比较给定官能团的Me 2 N ⋯ C和MeO ⋯ C距离，提出Me 2 N ⋯ C相互作用具有诱人的成分如果Me 2 N ⋯ C的分离度小于〜（MeO ⋯C + 0.15）Å，后者是由键合的较大尺寸引起的 氮原子。