萘酚 | 90-15-3

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 萘酚
• 中文别名: 1-甲萘酚；唛可奈因；1-萘酚；α-羟基萘；a-萘酚；ALPHA-萘酚；Α-羥萘；1-羟基萘；α-萘酚；甲萘酚
• 英文名称: α-naphthol
• 英文别名: 1-Naphthol；naphthalen-1-ol；naphthol；1-hydroxynaphthalene；alpha-naphthol；naphthalene-1-ol；1-naphthalenol；1-naphtol
• CAS: 90-15-3；1321-67-1
• 化学式: C₁₀H₈O
• mdl: MFCD00003930
• 分子量: 144.173
• InChiKey: KJCVRFUGPWSIIH-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96 °C(lit.)
• 沸点：
  278-280 °C(lit.)
• 密度：
  1.224
• 蒸气密度：
  4.5 (120 °C, vs air)
• 闪点：
  125 °C
• 溶解度：
  易溶于苯、氯仿、乙醚和乙醇。
• 最大波长(λmax)：
  324nm(MeOH)(lit.)
• LogP：
  2.84 at 25℃
• 物理描述：
  PelletsLargeCrystals
• 颜色/状态：
  Yellow monoclinic needles from water
• 气味：
  Phenolic odor
• 味道：
  Disagreeable, burning taste
• 蒸汽压力：
  1.7 mm Hg at 110 °C (2.74X10-4 mm Hg at 25 °C) /extrapolated to solid-phase/
• 亨利常数：
  6.00e-08 atm-m3/mole
• 大气OH速率常数：
  5.50e-10 cm3/molecule*sec
• 稳定性/保质期：
  Water stability: stable at pH < or =6.5; increased transformation with increased pH. /from table/
• 自燃温度：
  541.7 °C
• 分解：
  When heated to decomposition it emits acrid smoke and irritating fumes.
• 燃烧热：
  4957.4 kJ/mol (crystal) at 298.16 deg K; 5048.5 kJ/mol at 298.16 deg K (gas)
• 气味阈值：
  Recognition: 0.0030-0.0052 mg/cu m
• 折光率：
  Index of refraction: 1.6224 at 99 °C/D
• 解离常数：
  pKa = 9.34 at 25 °C
• 保留指数：
  1473.7;1494.9;1517;1484;1487;1494;1517;1483.7;1464;1483.5;1530;1490

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

产生1-萘基-α-D-葡萄糖苷...在丽蝇和蚱蜢中；在苍蝇和蚱蜢中产生1-萘基磷酸盐。/来自表格/

Yields 1-napthhyl-alpha-D-glucoside ... in blowfly and in grass grub; yields 1-naphthyl phosphate in fly and in grass grub. /from table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠、家兔、苍蝇和老鼠中产生1-萘基-β-D-葡萄糖醛酸苷。/来自表格/

Yields 1-naphthyl-beta-D-glucuronide in rat, in rabbit, in fly and in mouse. /from table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠、家兔、小鼠、豚鼠、苍蝇和金龟子中产生1-萘磺酸。/来自表格/

Yields 1-naphthyl sulfate in rat, rabbit, mouse, guinea pig, fly, and grass grub. /from table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在肠道循环（大鼠体内）中注入0.1毫摩尔1-萘酚后，肠道静脉血中有70-90%以1-萘酚葡萄糖苷酸的形式存在。对于1.0和2.0毫摩尔的注射，以1-萘酚葡萄糖苷酸形式存在的1-萘酚比例是25-50%。

After 0.1 mmol 1-naphthol injected into intestinal loops (rat in vivo), 70-90% in intestinal venous blood was present as 1-naphthol glucuronide. For 1.0 and 2.0 mmol injections, proportion of 1-naphthol present as 1-naphthol glucuronide was 25-50%.

来源:Hazardous Substances Data Bank (HSDB)

代谢

1-萘酚已知的人类代谢物包括1-萘基葡萄糖醛酸苷。

1-Naphthol has known human metabolites that include 1-Naphthyl glucuronide.

来源:NORMAN Suspect List Exchange

毒理性

• 毒性总结

1-萘酚是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。胆碱酯酶抑制剂（或“抗胆碱酯酶”）抑制乙酰胆碱酯酶的作用。由于其基本功能，干扰乙酰胆碱酯酶作用的化学物质是强大的神经毒素，低剂量时会导致过度流涎和流泪，随后是肌肉痉挛，最终导致死亡。神经气体和许多用于杀虫剂的物质已被证明通过结合乙酰胆碱酯酶活性位点的丝氨酸，完全抑制该酶。乙酰胆碱酯酶分解神经递质乙酰胆碱，后者在神经和肌肉接头处释放，以允许肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并继续发挥作用，使得任何神经冲动不断传递，肌肉收缩不会停止。最常见的乙酰胆碱酯酶抑制剂之一是基于磷的化合物，它们被设计用来结合到酶的活性位点上。结构要求是一个带有两个亲脂性基团的磷原子，一个离去基团（如卤素或硫氰酸盐），以及一个末端的氧。

1-Naphthol is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

急性接触胆碱酯酶抑制剂可能会导致胆碱能危象，表现为严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、晕厥和抽搐。肌肉无力可能性增加，如果呼吸肌受累，可能会导致死亡。在运动神经积累的乙酰胆碱会导致神经肌肉接头处烟碱受体的过度刺激。当这种情况发生时，可能会看到肌肉无力、疲劳、肌肉痉挛、肌束震颤和麻痹的症状。当自主神经节积累乙酰胆碱时，这会导致交感系统中烟碱受体的过度刺激。与此相关的症状是高血压和低血糖。由于乙酰胆碱积累而在中枢神经系统中过度刺激烟碱乙酰胆碱受体，会导致焦虑、头痛、抽搐、共济失调、呼吸和循环抑制、震颤、全身无力，甚至可能昏迷。当由于副交感乙酰胆碱受体上乙酰胆碱过多而导致毒蕈碱过度刺激时，可能会出现视力障碍、胸部紧绷、由于支气管收缩引起的喘息、支气管分泌物增加、唾液分泌增加、流泪、出汗、肠蠕动和排尿的症状。对于男性和女性的生育、生长和发育，已经特别将与有机磷农药暴露联系起来。关于生殖影响的大多数研究都是在农村地区使用杀虫剂和杀虫剂的农民进行的。在女性中，月经周期紊乱、怀孕时间延长、自然流产、死产以及后代的一些发育效应与有机磷农药暴露有关。产前暴露与胎儿生长和发育受损有关。神经毒性效应也与人因接触有机磷农药而中毒引起的四种神经毒性效应有关：胆碱能综合症、中间综合症、有机磷诱导的迟发性多发性神经病（OPIDP）和慢性有机磷诱导的神经精神障碍（COPIND）。这些综合症在急性接触和慢性接触有机磷农药后出现。

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

低剂量暴露的症状包括过度流涎和眼泪。急性剂量症状包括严重恶心/呕吐、流涎、出汗、心动过缓、低血压、虚脱和抽搐。肌肉无力可能会逐渐加剧，如果呼吸肌肉受影响，可能会导致死亡。还可能出现高血压、低血糖、焦虑、头痛、震颤和共济失调。

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 副作用

职业性肝毒素 - 第二性肝毒素：在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒案例。 肾毒素 - 该化学品在职业环境中可能对肾脏有毒。 溶血性贫血 - 血红蛋白或红细胞数量减少。

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting. Hemolytic anemia - Decreased hemoglobin or number of red blood cells.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

吸收、分配和排泄

经皮涂抹(14)C标记的1-萘醇后，尿液中(14)C的排泄表明，约50%通过人体皮肤被吸收。

Urinary excretion of (14)C following topical application of ((14)C)naphth-1-ol indicated that about 50% was absorbed percutaneously in man.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

一家碳化工厂的六十二名工人接触了苯、萘、甲苯、邻二甲苯、对二甲苯、酚和吡啶，并接受了检查。在职业暴露前后的尿样中，酚（21.7-97.6 mg/l）、1-萘酚（0.1-9.38 mg/l）、马尿酸（95.5-873.9 mg/l）和间甲基马尿酸（29.0-93.5 mg/l）的浓度值存在显著差异。焦化厂工人的呼吸区域空气中的苯和萘与尿液中的酚和1-萘酚之间存在相关性。

Sixty-two workers of a carbochemical plant exposed to benzene, naphthalene, toluene, o-xylene, p-xylene, phenol and pyridine were examined. In urine samples collected before and after occupational exposure significant differences in concn values of phenol (21.7-97.6 mg/l), 1-naphthol (0.1-9.38 mg/l), hippuric acid (95.5-873.9 mg/l) and m-methylhippuric acid (29.0-93.5 mg/l) were found. There was a correlation between benzene and naphthalene in the breathing zone air and phenol and 1-naphthol in the urine of coke plant workers.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

处理杂酚油浸渍木材的装配工和一名凿煤焦油沥青层的工人的化学暴露通过测量空气中的萘和多种多环芳烃以及测定尿中1-萘酚和1-芘醇的排泄来进行评估。当凿煤时，多环芳烃的总浓度和多环芳烃中含4-6个芳香环的浓度都很高，分别为440微克/立方米和290微克/立方米。在装配工的工作场所，多环芳烃的浓度约为这个值的1/50。关于空气中的萘浓度，情况则相反（装配工，1000微克/立方米；凿煤工，160微克/立方米）。相应地，装配工的尿中1-萘酚浓度是凿煤工的15-20倍。凿煤工的尿中1-芘醇浓度比装配工高2-4倍。由于估计的装配工吸入了的芘的剂量仅能解释尿中24小时芘醇排泄的2%-25%，因此皮肤很可能是主要的吸收途径。

Chemical exposure of assemblers handling creosote impregnated wood and of a single worker chiselling coal tar pitch layer was assessed by measuring airborne naphthalene and various polycyclic aromatic hydrocarbons, and by measurement of urinary excretion of 1-naphthol and 1-pyrenol. The sum concn polycyclic aromatic hydrocarbon and of 4-6 aromatic ring containing polycyclic aromatic hydrocarbons were high, 440 ug/cu m and 290 ug/cu m, respectively, when chiselling. In the assemblers workplace, the polycyclic aromatic hydrocarbons concn were about 1/50 of this value. Regarding airborne naphthalene concn the situation was reversed (assemblers, 1000 ug/cu m; chiseller, 160 ug/cu m). Correspondingly, the assemblers urinary 1-naphthol concn were 15-20 times higher than those of the chiseller. The urinary 1-pyrenol concn of the chiseller was 2-4 times higher than among the assemblers. As the estimated pyrene inhalation doses among the assemblers could account only for 2%-25% of the 24 hr pyrenol excretion in the urine, the skin was presumably the main route of uptake. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

以每千克体重45毫克的α-萘酚经口给药，导致雄性小鼠在处理后72小时内排除了95%的给药剂量。

Oral administration of 45 mg alpha-Naphthol/kg bw resulted in 95% of the administered dose being eliminated within 72 hr after treatment in male mice.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 危险品标志：
  Xn
• 安全说明：
  S2,S22,S26,S37/39
• 危险类别码：
  R21/22,R41,R37/38
• WGK Germany：
  1
• 海关编码：
  2907151000
• 危险品运输编号：
  UN 1759
• 危险类别：
  6.1
• RTECS号：
  QL2800000
• 包装等级：
  III
• 危险标志：
  GHS05,GHS06,GHS09
• 危险性描述：
  H302,H311,H315,H318,H335,H411
• 危险性防范说明：
  P273,P280,P302 + P352 + P312,P305 + P351 + P338 + P310,P501

制备方法与用途

1-萘酚是一种重要的有机化工原料，主要用于染料、医药、农药等领域。以下是关于1-萘酚的主要生产和应用信息：

生产方法

1. α-萘磺酸碱熔法

   • 以萘为原料，用浓硫酸低温(40℃以下)磺化得到α-萘磺酸。
   • 再在310～320℃碱熔可制得1-萘酚。

2. α-萘胺水解法

   • 原料：α-萘胺
   • 在15％～20％的硫酸中加压水解，反应温度为200℃，压力为1.2～1.5 MPa。
   • 反应产物分离后，经中和、蒸馏得到96％～98％的1-萘酚。

3. 四氢萘法

   • 以萘为原料，加氢制备四氢萘。
   • 经过氧化、脱氢等步骤最终生成1-萘酚。

生产工艺流程

1. 萘在“绝热”反应装置中进行加氢制备四氢萘。条件包括压力3MPa，平均温度300℃，转化率85%，选择性92%以上。

2. 四氢萘在多节鼓泡塔连续液相氧化生成四氢萘酮，采用乙酸铬和2-甲基-5-乙基吡啶复合催化剂。条件为压力常压，温度130℃，转化率20%，选择性90%以上。

3. 四氢萘酮在固定床反应器中脱氢制备1-萘酚，采用铂/粗孔硅胶或铂/活性氧化铝催化剂。加料空速0.8h^-1，转化率约85%，收率达到93%以上。

原料消耗与副产品处理

生产每吨甲萘酚需原料消耗定额：萘1.39 t，氢气600m³。

• 该工艺总收率为65.4%。
• 优点包括工艺合理、技术先进、原料易得（除萘外主要为氢和空气）、产品质量高且不含β-异构体。

应用领域

1. 染料：作为多种染料的中间体，如偶氮类、三芳甲烷类等。
2. 医药：可用于合成某些药物。
3. 农药：用于制造杀虫剂和其他农药品种。
4. 其他用途：还可应用于纺织助剂等领域。

综上所述，1-萘酚因其多功能性而在多个行业中有着广泛的应用，并且随着技术的进步，其生产过程也在逐步优化。

反应信息

• 作为反应物：
  描述：

  萘酚 在 三氯化磷 作用下， 生成 1-naphthyloxydichlorophosphine
  参考文献：
  名称：

  Kunz, Chemische Berichte, 1894, vol. 27, p. 2563

  摘要：

  DOI：
• 作为产物：
  描述：

  1-萘胺 在 uranyl nirate hexahydrate 、 水 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以54%的产率得到萘酚
  参考文献：
  名称：

  一种芳基酚类化合物及其合成方法和应用

  摘要：

  本发明公开了一种式(3)芳基酚类化合物的合成方法。所有体系在空气或者氮气氛围中进行，利用可见光激发光敏剂催化。在反应溶剂中，以式(1)ArNR1R2和式(2)水为反应原料，在酸的辅助作用下，反应得到式(3)芳基酚类化合物。本发明式(1)ArNR1R2可以是一级胺、三级胺，也可以是甾体、氨基酸类衍生物，还可以是丙泊酚、扑热息痛、布洛芬、奥沙普秦、吲哚美辛类等药物或者衍生物。本发明合成方法原料廉价易得，反应操作简单，反应条件温和，反应收率较高，底物官能团兼容性好。本发明流体反应不仅可以实现基础化工品的放大，还可以实现精细化工品的放大，如药物丙泊酚、扑热息痛的合成。本发明具有广泛的应用前景和使用价值。

  公开号：

  CN112778125B
• 作为试剂：
  描述：

  4-(1-羟基乙基)苯甲腈 在 萘酚 、 C₁₃₆H₁₀₂Fe₂N₄O₆ 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以42%的产率得到(R)-1-(4-氰基苯基)乙醇
  参考文献：
  名称：

  仲醇与萘氧化物结合的铁（salan）配合物的有氧氧化动力学拆分

  摘要：

  铁催化的仲醇有氧氧化动力学分辨率的第一个通用方法是通过良好到高对映体分化（k(rel) = 7-50）实现的。尽管铁 (salan) 络合物 1 不催化醇氧化，但与萘氧化物结合的铁 (salan) 络合物可以。

  DOI：

  10.1021/ja204426s

文献信息

• [EN] IMIDAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS IMIDAZOLE UTILES COMME INHIBITEURS DE LA FAAH
  申请人：MERCK & CO INC

  公开号：WO2009152025A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzeimer Disease, and Parkinson's Disease.

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病性神经病、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• [EN] PYRAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2009151991A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzheimer disease, and Parkinson's disease

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• Central nervous system antiischemic agents
  申请人：Bristol-Myers Squibb Company

  公开号：EP0559569A1

  公开（公告）日：1993-09-08

  A series of phenylalkylaminoalkyl derivatives of Formula I wherein Ar is naphtyl or phenyl;    R¹ is hydrogen, fluoro or R⁴CONH-;    R² is hydrogen or C₁-₆ alkyl;    R₃ is C₁-₆ alkyl;    R⁴ is C₁-₆ alkyl or phenyl- C₁-₆ alkyl;    x is zero or the integers 1 and 2;    m is selected from the integers 1 to 6; and    n is selected from the integers 2 and 3, has been found to provide effective antiischemic protection for CNS tissue, particularly neurons. A method of treatment to protect against CNS ischemia, such as that resulting from trauma or stroke or other ischemic conditions, comprises administration of these novel compounds to an individual in need of such treatment.

  一系列的Formula I的苯基烷基氨基烷基衍生物已被发现能够为中枢神经系统组织，特别是神经元，提供有效的抗缺血保护。一种治疗方法用于保护中枢神经系统缺血，例如由创伤、中风或其他缺血病症引起的缺血情况，包括将这些新化合物用于需要此类治疗的个体。其中Ar为萘基或苯基；R¹为氢、氟或R⁴CONH-；R²为氢或C₁-₆烷基；R₃为C₁-₆烷基；R⁴为C₁-₆烷基或苯基-C₁-₆烷基；x为零或整数1和2；m从整数1到6中选择；n从整数2和3中选择。
• CHLORO-PYRAZINE CARBOXAMIDE DERIVATIVES WITH EPITHELIAL SODIUM CHANNEL BLOCKING ACTIVITY
  申请人：Parion Sciences, Inc.

  公开号：US20140171447A1

  公开（公告）日：2014-06-19

  This invention provides compounds of the formula I: and their pharmaceutically acceptable salts, useful as sodium channel blockers, compositions containing the same, therapeutic methods and uses for the same and processes for preparing the same.

  这项发明提供了式I的化合物及其药用盐，可用作钠通道阻滞剂，包含这些化合物的组合物，以及用于这些化合物的治疗方法和用途，以及制备这些化合物的方法。
• Chiral 2-(2-hydroxyaryl)alcohols (HAROLs) with a 1,4-diol scaffold as a new family of ligands and organocatalysts
  作者：Ömer Dilek、Mustafa A. Tezeren、Tahir Tilki、Erkan Ertürk

  DOI：10.1016/j.tet.2017.11.054

  日期：2018.1

  Efficient and modular syntheses of chiral 2-(2-hydroxyaryl)alcohols (HAROLs), novel 1,4-diols carrying one phenolic and one alcohol hydroxyl group, have been developed which led to generation of a small library of structurally diverse HAROLs in enantiomerically pure form. Of the different HAROLs examined, a HAROL based on the indan backbone exhibited the highest activity and enantioselectivity in the

  高效和模块化的手性2-（2-羟基芳基）醇（HAROLs）的合成，带有一个酚和一个醇羟基的新型1,4-二醇已被开发出来，这导致在对映异构体中生成结构多样的HAROLS小文库纯形式。在考察的不同HAROL中，基于茚满骨架的HAROL在Ti（O i Pr）4（y高达97％， 88％ee）并在三田膦的促进下在Morita-Baylis-Hillman反应中作为氢键供体有机催化剂发挥作用。

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