6,7-二羟基-3,4-二氢-1(2H)-萘酮 | 54549-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 6,7-二羟基-3,4-二氢-1(2H)-萘酮
• 英文名称: 6,7-dihydroxy-1-tetralone
• 英文别名: 6,7-dihydroxy-3,4-dihydro-1(2H)-naphthalenone；1(2H)-Naphthalenone, 3,4-dihydro-6,7-dihydroxy-；6,7-dihydroxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 54549-75-6
• 化学式: C₁₀H₁₀O₃
• mdl: MFCD18648084
• 分子量: 178.188
• InChiKey: POBJBWINAQGAEP-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C(Solv: water (7732-18-5))
• 沸点：
  434.4±45.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  6,7-二羟基-3,4-二氢-1(2H)-萘酮 在 potassium fluoride 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 8-(3-bromopropoxy)-9-methoxy-12-methyl-5,6-dihydro-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]acridin-12-ium trifluoromethanesulfonate
  参考文献：
  名称：

  12-N-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for c-myc G-quadruplex DNA

  摘要：

  12-N-Methylated and non-methylated 5,6-dihydrobenzo[c]acridine derivatives were designed and synthesized as new series of c-myc G-quadruplex binding ligands. Their interactions with c-myc G-quadruplex were evaluated using fluorescence resonance energy transfer (FRET) melting assay, circular dichroism (CD) spectroscopy, surface plasmon resonance (SPR), polymerase chain reaction (PCR) stop assay, and molecular modeling. Compared with the non-methylated derivatives, 12-N-methylated derivatives had stronger binding affinity and stabilizing ability to c-myc G-quadruplex structure, and could more effectively stack on the G-quartet surface. All these derivatives had high selectivity for c-myc G-quadruplex DNA over duplex DNA. The reverse transcription (RT) PCR assay showed that compound 21c could down-regulate transcription of c-myc gene in Ramos cell line containing NHE III1 element, but had no effect in CA46 cell line with NHE III1 element removed. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.034
• 作为产物：
  描述：

  4-(3,4-二甲氧苯基)丁酸 在 trimethylammonium heptachlorodialuminate 作用下， 以50%的产率得到6,7-二羟基-3,4-二氢-1(2H)-萘酮
  参考文献：
  名称：

  氯铝酸盐离子液体试剂裂解芳香族甲基醚

  摘要：

  我们意外地发现氯铝酸盐离子液体可以在令人惊讶的温和条件下裂解芳香族甲基醚。三种离子液体，即。[TMAH][Al2Cl7]、[BMIM][Al2Cl7]、[EMIM][Al2Cl6I] 和氯化铝在 4-甲氧基官能团的 4,5-二甲氧基茚满酮的选择性去甲基化中进行了比较。与氯化铝 (70:30) 相比，离子液体表现出非常高的选择性 (96:4)。此外，当使用离子液体时，反应时间大大缩短。有趣的是，这三种离子液体在 4,5-二甲氧基茚满酮的去甲基化反应中表现出相同的反应性。考虑到 [TMAH][Al2Cl7] 前体的较低成本和大量可用性，我们得出结论，从工业角度来看，这是最具吸引力的离子液体。为了使 [TMAH][Al2Cl7] 的大规模应用可行，我们开发了一种安全的、可升级的制备方法。此外，研究了离子液体试剂[TMAH][Al2Cl7]对醚裂解的范围，发现芳香甲基-、烯丙基-和苄基-醚裂解适用于多种杂环化合物。(©

  DOI：

  10.1002/ejoc.200210666

文献信息

• 1,4-disubstituted piperazines (or homopiperazines) as
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04880809A1

  公开（公告）日：1989-11-14

  Novel 1,4-disubstituted piperazine compounds represented by the formula (I): ##STR1## wherein A is a condensed polycyclic hydrocarbon group; R is a phenyl group substituted with a lower alkoxy group; X is methylene group, carbonyl group or thiocarbonyl group; and m is 2 or 3, and their salts are useful as a platelet activating factor antagonist.

  新颖的1,4-二取代哌嗪化合物由以下公式（I）表示：##STR1## 其中A是一个紧凑的多环碳氢基团；R是一个被低烷氧基取代的苯基团；X是亚甲基基团、羰基或硫代羰基；m为2或3，它们的盐可用作血小板活化因子拮抗剂。
• Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (<i>n+1</i>)-Halomethyl-Alkanes
  作者：Margherita Miele、Andrea Citarella、Thierry Langer、Ernst Urban、Martin Zehl、Wolfgang Holzer、Laura Ielo、Vittorio Pace

  DOI：10.1021/acs.orglett.0c02831

  日期：2020.10.2

  The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high

  据报道，将类胡萝卜素和氢化物顺序安装在羰基上，提供了卤代甲基烷基衍生物。尽管在与以碳为中心的亲电子试剂的反应中使用类胡萝卜素作为亲核试剂，sp 3型烷基卤化物仍然是用于选择性一碳同系物的难以捉摸的材料。我们的策略是利用羰基化合物作为起始原料，从而能够均匀地实现高收率和化学控制。该策略是灵活的，不仅限于类胡萝卜素。而且，各种类似碳负离子的物种可以充当亲核试剂，因此使其具有普遍的适用性。
• [EN] NAPTHOQUINONES, PRO-DRUGS, AND METHODS OF USE THEREOF<br/>[FR] NAPHTOQUINONES, PROMÉDICAMENTS, ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV TEXAS

  公开号：WO2017106624A1

  公开（公告）日：2017-06-22

  Provided herein are naphthoquinones compounds such as those with a hydrogen bond donating group of the formula (I): wherein: R1, R2, R3, R4, R5, and n are as defined herein. Also provided herein are pharmaceutical composition of the present compounds and methods of treatment using the compounds including their use in the treatment of cancer.

  提供在本说明书中的萘醌化合物，例如具有式(I)中的氢键供体基团的那些：其中：R1、R2、R3、R4、R5和n如本文所述定义。此外，还提供了本化合物的药物组合物以及使用这些化合物进行治疗的方法，包括它们在癌症治疗中的应用。
• Synthesis of Arnottin I through a Palladium-Mediated Aryl-Aryl Coupling Reaction.
  作者：Takashi HARAYAMA、Hirotake YASUDA、Toshihiko AKIYAMA、Yasuo TAKEUCHI、Hitoshi ABE

  DOI：10.1248/cpb.48.861

  日期：——

  6H-Dibenzo[b,d]pyran-6-one, 6H-benzo[d]naphtho[1,2-b]pyran-6-one, and their derivatives were prepared via the palladium mediated aryl-aryl coupling reaction of aryl ortho-halobenzoate. The short step synthesis of arnottin I(1) was achieved by this method.

  6H-二苯并[b，d]吡喃-6-一，6H-苯并[d]萘并[1,2-b]吡喃-6-及其衍生物是通过钯介导的芳基芳基-芳基偶联反应制备的邻卤代苯甲酸酯。通过这种方法可以实现Arnottin I（1）的短时合成。
• Synthesis and Platelet-Activating Factor (PAF)-Antagonistic Activities of 1,4-Disubstituted Piperazine Derivatives.
  作者：Hideto FUKUSHI、Hiroshi MABUCHI、Katsumi ITOH、Zen-ichi TERASHITA、Kohei NISHIKAWA、Hirosada SUGIHARA

  DOI：10.1248/cpb.42.541

  日期：——

  platelet-activating factor (PAF) antagonists, we found that 1-(6-methoxy-3,4-dihydro-2-naphthoyl)-4- (3,4,5-trimethoxybenzyl)piperazine and its 4-(3,4,5- trimethoxybenzoyl)piperazine derivatives (1b, 2b) exerted in vitro and in vivo PAF-antagonistic activities. Modifications of the 1-acyl group, the substituent at the 4-position and the piperazine ring of 1a and 2b were examined and from this series 1-(2,3-dimethoxy-6

  在筛选新型血小板活化因子（PAF）拮抗剂的过程中，我们发现1-（6-甲氧基-3,4-二氢-2-萘甲酰基）-4-（3,4,5-三甲氧基苄基）哌嗪及其4 -（3,4,5-三甲氧基苯甲酰基）哌嗪衍生物（1b，2b）在体内和体外具有PAF拮抗活性。检查了1a和2b的1-酰基，4-位取代基和哌嗪环的修饰，并从该系列的1-（2,3-二甲氧基-6,7-二氢-5H-苯并环庚烯-8-发现羰基++（+）-4-（3,4,5-三甲氧基苯甲酰基）哌嗪（2g）是最有效的PAF拮抗剂之一。