1-cyanomethyl-2-naphthol | 4855-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-cyanomethyl-2-naphthol
• 英文别名: (2-hydroxy-[1]naphthyl)-acetonitrile；(2-Hydroxy-[1]naphthyl)-acetonitril；(2-hydroxy-naphthalen-1-yl)-acetonitrile；2-(2-hydroxy-1-naphthyl)acetonitrile；<2-Hydroxy-1-naphthyl>acetonitril；1-Cyanmethyl-<2>naphthol；1-Naphthaleneacetonitrile, 2-hydroxy-；2-(2-hydroxynaphthalen-1-yl)acetonitrile
• CAS: 4855-11-2
• 化学式: C₁₂H₉NO
• 分子量: 183.21
• InChiKey: LBKOFRPWHDKPDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-cyanomethyl-2-naphthol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙二醇甲醚 为溶剂， 生成 1-(2-amino-ethyl)-[2]naphthol
  参考文献：
  名称：

  Short,J.H.; Ours,C.W., Journal of Heterocyclic Chemistry, 1975, vol. 12, p. 869 - 876

  摘要：

  DOI：
• 作为产物：
  描述：

  2-nitro-3-phenyl-3H-naphtho<2,1-b>pyran 在 五氯化磷 、 镍 、 一水合肼 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.0h， 生成 1-cyanomethyl-2-naphthol
  参考文献：
  名称：

  Synthesis and Reactivity of 1,1-Dihydro-2-oximino-3-aryl-3H-naphtho[2,1-b]pyrans

  摘要：

  A series of 1,1-dihydro-2-oximino-3-arylnaphtho[2,1-b]pyrans were synthesised in good yields by reduction of the corresponding 2-nitronaphthopyrans using Raney Nickel and hydrazine hydrate or sodium borohydride in ethanol. Further, the Beckmann rearrangement product on the oxime using phosphorous pentachloride in ether was identified as 1-cyanomethyl-2-naphthol. Whereas using sulfuric acid as the catalyst the product was characterised as 4-arylnaphth[1,2-0[1,4]oxazepine.

  DOI：

  10.3987/com-89-5029

文献信息

• Silicon-Induced General, Mild, and Efficient One-Pot, Three-Component Synthesis of Amidoalkyl Naphthol Libraries
  作者：Tarek Salama

  DOI：10.1055/s-0032-1318392

  日期：——

  A general mild and efficient protocol for the synthesis of amidoalkyl naphthol libraries was achieved utilizing tetrachlorosilane and zinc chloride in dichloromethane at ambient temperature via a one-pot, three-component condensation of various aldehydes, nitriles (amides), and β-naphthol.

  在室温下，通过各种醛、腈（酰胺）和 β-萘酚的一锅三组分缩合反应，在二氯甲烷中使用四氯硅烷和氯化锌，实现了合成酰胺烷基萘酚库的一般温和有效的方案。
• Method for the treatment of CNS disorders with substituted 2-imidazoles or imidazole derivatives
  申请人：Galley Guido

  公开号：US20070197621A1

  公开（公告）日：2007-08-23

  The present invention relates a method for treating depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders which comprises administering to an individual a therapeutically effective amount of a compound of formula I wherein R, R 1 , R 2 , A and n are as defined in the specification and to their pharmaceutically active salts. The invention also relates to novel compounds of formula I, pharmaceutical compositions containing them, and methods for their preparation.

  本发明涉及一种治疗抑郁症、焦虑症、双相情感障碍、注意力缺陷多动障碍、压力相关障碍、精神分裂症等精神障碍、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用、进食障碍、糖尿病、糖尿病并发症、肥胖症、血脂异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍以及心血管疾病的方法，包括向个体施用化合物I的治疗有效量，其中R、R1、R2、A和n如规范中所定义，以及其药用活性盐。该发明还涉及化合物I的新颖化合物、含有它们的药物组合物以及它们的制备方法。
• New bicyclic antidepressant agent. Synthesis and activity of napactadine and related compounds
  作者：James R. McCarthy、Donald L. Wright、Albert J. Schuster、Abdul H. Abdallah、Philip J. Shea、Randy Eyster

  DOI：10.1021/jm00149a031

  日期：1985.11

  A number of N,N'-dialkylarylamidines were synthesized and evaluated for antidepressant activity. Several of these compounds were synthesized from the corresponding nitriles by a new method. Slight structural modification in the series caused a marked change in biological activity and led to compounds as active as imipramine. The arylacetamidine, N,N'-dimethyl-2-naphthaleneethanimidamide hydrochloride

  合成了许多N，N′-二烷基芳基idine胺并评估了其抗抑郁活性。这些化合物中的几种是通过新方法由相应的腈合成的。系列中的轻微结构修饰导致生物学活性发生显着变化，并导致化合物的活性与丙咪嗪一样。选择芳基乙am，N，N'-二甲基-2-萘乙酰胺酰胺盐酸盐（33）（那帕他定）进行临床研究。制备了48种33的其他类似物，包括许多N-烷基am。
• Catalyst-free synthesis of benzofuran-fused pyrido[4,3-d]pyrimidines from 2-(2-hydroxyaryl)acetonitrile and 4,6-dichloropyrimidine-5-carbaldehyde through domino condensation reactions
  作者：Bo Li、Zhizhou Yue、Haoyue Xiang、Linlin Lv、Shanshan Song、Zehong Miao、Chunhao Yang

  DOI：10.1039/c3ra44828b

  日期：——

  A rapid, one-pot, catalyst-free approach to novel benzofuran-fused pyrido[4,3-d]pyrimidines with good antitumor activities via a cascade SNAr/cyclization/condensation reaction through 2-(2-hydroxyphenyl)acetonitriles and 4,6-dichloropyrimidine-5-carbaldehyde was developed.

  一种快速，一锅煮，不含催化剂的方法来新颖苯并呋喃稠合的吡啶并[4,3- d ]具有良好的抗肿瘤活性的嘧啶经由级联小号Ñ的Ar /环化/缩合反应通过2-（2-羟基苯基）乙腈和开发了4，6-二氯嘧啶-5-甲醛。
• Alkanoic acid derivatives process for their production and use thereof
  申请人：——

  公开号：US20040058965A1

  公开（公告）日：2004-03-25

  An alkanoic acid derivative useful as a prophylactic or therapeutic agent of diabetes mellitus, hyperlipidemia, impaired glucose tolerance and the like can be provided by a compound represented by the formula 1 wherein R 1 is an optionally substituted 5-membered aromatic heterocyclic group; X is a bond and the like; Q is a divalent hydrocarbon group having 1 to 20 carbon atoms; Y is a bond and the like, ring A is an aromatic ring optionally further having 1 to 3 substituents; Z is —(CH 2 ) n —Z 1 — (n is an integer of 1 to 8 and Z 1 is an oxygen atom and the like) and the like; ring B is a pyridine ring optionally further having 1 to 3 substituents, and the like; U is a bond and the like; W is a divalent hydrocarbon group having 1 to 20 carbon atoms; and R 3 is —OH and the like, provided that, when ring B is a benzene ring optionally further having 1 to 3 substituents, U should be a bond, or a salt thereof.

  一种可以用作糖尿病、高脂血症、糖耐量受损等预防或治疗剂的脂肪酸衍生物可以由以下式1所表示的化合物提供，其中R1是可选取代的5-成员芳香杂环基；X是键等；Q是具有1到20个碳原子的二价碳氢基团；Y是键等；环A是一种芳香环，可选择进一步具有1到3个取代基；Z是—（CH2）n—Z1—（n是1到8的整数，Z1是氧原子等）等；环B是吡啶环，可选择进一步具有1到3个取代基等；U是键等；W是具有1到20个碳原子的二价碳氢基团；R3是—OH等；但是，当环B是苯环，可选择进一步具有1到3个取代基时，U应为键，或其盐。