2-[2'-(hydroxymethyl)-1'-naphthyl]phenol | 145497-43-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[2'-(hydroxymethyl)-1'-naphthyl]phenol
• 英文别名: 2-(2-(hydroxymethyl)-naphthalen-1-yl)-phenol；2-[2-(Hydroxymethyl)naphthalen-1-yl]phenol
• CAS: 145497-43-4
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: LDIISCWZGRJWLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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'-(hydroxymethyl)-1'-naphthyl]phenol 以 水 、 乙腈 为溶剂， 生成 6H-naphtho[2,1-c]chromene
  参考文献：
  名称：

  Photocyclization of a 1,1′-bisnaphthalene: planarization of a highly twisted biaryl system after excited state ArOH dissociation

  摘要：

  在 MeCN 水溶液中，高度扭曲的 1,1â²-双萘 6 被光解，得到平面度更高的二萘并吡喃 10，且量子产率很高（δ = 0.17）。

  DOI：

  10.1039/a606487f
• 作为产物：
  描述：

  6H-naphtho[2,1-c]chromen-6-one 在 lithium aluminium tetrahydride 作用下， 生成 2-[2'-(hydroxymethyl)-1'-naphthyl]phenol
  参考文献：
  名称：

  Photocyclization of a 1,1′-bisnaphthalene: planarization of a highly twisted biaryl system after excited state ArOH dissociation

  摘要：

  在 MeCN 水溶液中，高度扭曲的 1,1â²-双萘 6 被光解，得到平面度更高的二萘并吡喃 10，且量子产率很高（δ = 0.17）。

  DOI：

  10.1039/a606487f

文献信息

• Tetralones as precursors for the synthesis of 2,2′-disubstituted 1,1′-binaphthyls and related compounds
  作者：Simon S. Moleele、Joseph P. Michael、Charles B. de Koning

  DOI：10.1016/j.tet.2008.08.079

  日期：2008.11

  Using tetralones as starting materials, the synthesis of biaryl compounds is described in this paper. The tetralones were initially converted into 1-bromo-3,4-dihydro-2-naphthalenecarbaldehydes before effecting aromatization into the corresponding naphthalenes. These products were then subjected to Suzuki–Miyaura cross-coupling reactions, with a variety of aromatic boronic acids containing substituents

  本文以四氢萘酮为起始原料，描述了联芳基化合物的合成。首先将四氢萘酮转化为1-溴-3,4-二氢-2-萘甲醛，然后进行芳构化成相应的萘。然后将这些产物与在邻位含有取代基的各种芳香族硼酸进行铃木-宫浦交叉偶联反应，制得联芳基化合物。联芳基化合物具有含杂原子的取代基的邻位到新形成的二芳基轴。
• [DE] MEDIZINISCH NÜTZLICHE 1-PHENYL-2-AMINOMETHYLNAPTHTALINE, VERFAHREN ZU IHRER HERSTELLUNG, SIE ENTHALTENDE ARZNEIMITTEL UND DEREN VERWENDUNG<br/>[EN] MEDICALLY USEFUL 1-PHENYL-2-AMINOMETHYL NAPHTHALENES, METHOD FOR PRODUCING THEM, DRUGS CONTAINING THEM AND USE THEREOF<br/>[FR] 1-PHENYL-2-AMINOMETHYLNAPHTALINES A USAGE MEDICAL, PROCEDES DE FABRICATION DE CES COMPOSES, MEDICAMENTS CONTENANT CES COMPOSES ET UTILISATION DE CEUX-CI
  申请人：UNIV MAINZ JOHANNES GUTENBERG

  公开号：WO2004065349A1

  公开（公告）日：2004-08-05

  Es werden die Verbindungen 1-Phenyl-2-aminomethylnapthalin-Derivate der allgemeinen Formel (1) beschrieben sowie Verfahren zu ihrer Herstellung. 1-Phenyl-2-aminomethylnapthaline haben in Zellkulturmodellen Antitumor-Eigenschaften. Weiterhin stellen diese Substanzen Inhibitoren für neurodegenerative Erkrankungen dar und zeigen eine ausgeprägte antiprotozoische Aktivität.

  描述了通用公式（1）的1-苯基-2-氨甲基萘衍生物的连接以及它们的制备方法。在细胞培养模型中，1-苯基-2-氨甲基萘具有抗肿瘤特性。此外，这些物质还是神经退行性疾病的抑制剂，并显示出明显的抗原生动物活性。
• Photocyclization of a 1,1′-bisnaphthalene: planarization of a highly twisted biaryl system after excited state ArOH dissociation
  作者：Yijian Shi、Peter Wan

  DOI：10.1039/a606487f

  日期：——

  Photolysis of the highly twisted 1,1′-bisnaphthalene 6 gives the much more planar dinaphthopyran 10 with high quantum yield (Φ = 0.17) in aqueous MeCN, demonstrating that the expected enhanced electronic communication between the connected aromatic rings of biaryls in S 1 is sufficient to drive thermally unfavourable reactions requiring initial planarization of these biaryl systems.

  在 MeCN 水溶液中，高度扭曲的 1,1â²-双萘 6 被光解，得到平面度更高的二萘并吡喃 10，且量子产率很高（δ = 0.17）。
• ASYMMETRIC SYNTHESIS OF (M)-2-HYDROXYMETHYL-1-(2-HYDROXY-4,6-DIMETHYLPHENYL)NAPHTHALENE VIA A CONFIGURATIONALLY UNSTABLE BIARYL LACTONE
  作者：Bringmann, Gerhard、Breuning, Matthias、Henschel, Petra、Hinrichs, Jürgen、Greenen, Peter M.、Curran, Dennis P.

  DOI：10.15227/orgsyn.079.0072

  日期：——
• Biaryl hydroxy aldehydes as intermediates in the metal-assisted atropo-enantioselective reduction of biaryl lactones: Structures and aldehyde-lactol equilibria
  作者：Gerhard Bringmann、Matthias Breuning、Heike Endress、Daniel Vitt、Karl Peters、Eva-Maria Peters

  DOI：10.1016/s0040-4020(98)00618-8

  日期：1998.9

  The synthesis of substituted 1-(2'-hydroxyphenyl)naphthalene-2-carbaldehydes 4 and 6-alkoxy-6H-pyrans 7 and 8, analogs of the postulated metallated intermediates in the atropo-enantioselective ring cleavage of configuratively unstable biaryl lactones 2, is described. While the equilibria between the open hydroxy aldehydes 4 and the cyclic lactol structures 3 are completely shifted towards 4 for the derivatives 4c-g with substituents ortho to the biaryl axis, the lactol forms are the dominating structures (ca. 50-100%) for the ortho-unsubstituted compounds. For the lactols 3 and their acetalic analogs 6, 7, and 8, those diastereomeric conformations are preferred (77-100%) that have the exo-oxygen function axial. (C) 1998 Elsevier Science Ltd. All rights reserved.