5-methoxy-3,4-dihydronaphthalene-2-carbonitrile | 2825-47-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-methoxy-3,4-dihydronaphthalene-2-carbonitrile
• 英文别名: 2-Cyano-5-methoxy-3,4-dihydronaphthalene
• CAS: 2825-47-0
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: UIRBTYLHDFGCBO-UHFFFAOYSA-N

物化性质

• 熔点：
  55-65 °C
• 沸点：
  342.8±41.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-3,4-dihydronaphthalene-2-carbonitrile 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-cyano-7,8-dihydro-1-naphthol
  参考文献：
  名称：

  (R)-(+)-2-[[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine Methanesulfonate:  A New Selective Rat 5-Hydroxytryptamine_1B Receptor Antagonist

  摘要：

  In the search for new 5-hydroxytryptamine (5-HT) receptor antagonists it was found that the compound (R)-(+)-2-[[[3-(morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine methanesulfonate, (R)-25, is a selective rat 5-hydroxytryptamine(1B) (r5-HT1B) receptor antagonist. The binding profile showed a 13-fold preference for r5-HT1B (K-i = 47 +/- 5 nM; n = 3) vs bovine 5-HT1B (K-i = 630 nM; n = 1) receptors. The compound had very low affinity for other monoaminergic receptors examined. The r5-HT1B receptor antagonism was demonstrated by the potentiation of the K+-stimulated release of [H-3]-5-HT from superfused rat brain slices in vitro, an effect that was antagonized by addition of 5-HT to the superfusion fluid. (R)-25 at 20 mg/kg sc enhanced the 5-HT turnover in four rat brain regions (hypothalamus, hippocampus, striatum, and frontal cortex) with about 40% measured as the 5-HTP accumulation after decarboxylase inhibition with 3-hydroxybenzylhydrazine. At 3 mg/kg sc (R)-25 produced a significant increase in the number of wet dog shakes in rats, a 5-HT2A/5-HT2C response that was abolished by depletion of 5-HT after pretreatment with the tryptophan hydroxylase inhibitor p-chlorophenylalanine. These observations show that (R)-25, by inhibiting terminal r5-HT1B autoreceptors, increases the 5-HT turnover and the synaptic concentration of 5-HT.

  DOI：

  10.1021/jm970806i
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 potassium phosphate 、 2,3-bis(dicyclohexylphosphino)thiophene 、 sodium hydride 、 nickel dibromide 、 锌 作用下， 以 四氢呋喃 、 甲苯 、 paraffin oil 为溶剂， 反应 36.58h， 生成 5-methoxy-3,4-dihydronaphthalene-2-carbonitrile
  参考文献：
  名称：

  镍催化用氨基乙腈氰化苯酚衍生物

  摘要：

  由简单的芳族原料化学物质产生有用的芳腈结构代表了化学合成中的根本重要反应。描述了苯酚衍生物用无金属的氰化剂，氨基乙腈的第一次镍催化的氰化。由独特的二膦配体（例如dcype或dcypt）组成的镍基催化体系能够使通用的酚衍生物（例如氨基甲酸芳基酯和新戊酸芳基酯）氰化。氨基乙腈作为氰化剂的使用导致芳基腈合成的环境和易于使用的方法。

  DOI：

  10.1021/acs.orglett.6b02265

文献信息

• Phenylethanolaminomethyltetralins and pharmaceutical use
  申请人：Sanofi

  公开号：US05130339A1

  公开（公告）日：1992-07-14

  New phenylethanolaminomethyltetralins of formula (I) ##STR1## wherein E represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, phenyl, nitro, halogen, or trifluoromethyl, L represents hydrogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkyoxy, phenyl, nitro, or halogen, or E and L taken together represent a group --CH.dbd.CH--CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, and G represents hydrogen, chloro, hydroxy or an --OG' group wherein G' represents a (C.sub.1 -C.sub.4 (alkyl group either unsubstituted or substituted with hydroxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkoxycarbonyl, carboxy, or (C.sub.3 -C.sub.7)cycloalkyl; a (C.sub.3 -C.sub.7)cycloalkyl group; or a (C.sub.2 -C.sub.4)alkanoyl group; and salts thereof, are described which showed to be active as intestinal motility modulating agents and intraocular hypertension lowering agents. Also described is a process for the preparation of the new compounds and the intermediates of formula (III) ##STR2## employed in said process.

  化合物公式为(I)的新苯乙醇胺基甲基四氢萘，其中E代表氢，(C1-C4)烷基，(C1-C4)烷氧基，苯基，硝基，卤素或三氟甲基，L代表氢，(C1-C4)烷基，(C1-C4)烷氧基，苯基，硝基或卤素，或E和L在一起代表一个基团--CH=CH-CH=CH-或--CH2-CH2-CH2-CH2-，G代表氢，氯，羟基或-OG'基团，其中G'代表(C1-C4)烷基，未取代或取代羟基，(C1-C4)烷氧基，(C1-C4)烷氧羰基，羧基或(C3-C7)环烷基；(C3-C7)环烷基；或(C2-C4)烷酰基；以及其盐，这些化合物表现出作为肠动力调节剂和降低眼内压的活性。还描述了制备新化合物和公式(III)的中间体的过程，该中间体在所述过程中使用。
• Phényléthanolaminométhyltétralines, procédé pour leur préparation et compositions pharmaceutiques les contenant
  申请人：ELF SANOFI

  公开号：EP0436435B1

  公开（公告）日：1994-03-23
• US5130339A
  申请人：——

  公开号：US5130339A

  公开（公告）日：1992-07-14
• Cyanation of Phenol Derivatives with Aminoacetonitriles by Nickel Catalysis
  作者：Ryosuke Takise、Kenichiro Itami、Junichiro Yamaguchi

  DOI：10.1021/acs.orglett.6b02265

  日期：2016.9.2

  nickel-catalyzed cyanation of phenol derivatives with metal-free cyanating agents, aminoacetonitriles, is described. A nickel-based catalytic system consisting of a unique diphosphine ligand such as dcype or dcypt enables the cyanation of versatile phenol derivatives such as aryl carbamates and aryl pivalates. The use of aminoacetonitriles as a cyanating agent leads to an environmentally and easy-to-use method

  由简单的芳族原料化学物质产生有用的芳腈结构代表了化学合成中的根本重要反应。描述了苯酚衍生物用无金属的氰化剂，氨基乙腈的第一次镍催化的氰化。由独特的二膦配体（例如dcype或dcypt）组成的镍基催化体系能够使通用的酚衍生物（例如氨基甲酸芳基酯和新戊酸芳基酯）氰化。氨基乙腈作为氰化剂的使用导致芳基腈合成的环境和易于使用的方法。
• (<i>R</i>)-(+)-2-[[[3-(Morpholinomethyl)-2<i>H</i>-chromen-8-yl]oxy]methyl]morpholine Methanesulfonate:  A New Selective Rat 5-Hydroxytryptamine_1B Receptor Antagonist
  作者：Stefan Berg、Lars-Gunnar Larsson、Lucy Rényi、Svante B. Ross、Seth-Olof Thorberg、Gun Thorell-Svantesson

  DOI：10.1021/jm970806i

  日期：1998.5.1

  In the search for new 5-hydroxytryptamine (5-HT) receptor antagonists it was found that the compound (R)-(+)-2-[[[3-(morpholinomethyl)-2H-chromen-8-yl]oxy]methyl]morpholine methanesulfonate, (R)-25, is a selective rat 5-hydroxytryptamine(1B) (r5-HT1B) receptor antagonist. The binding profile showed a 13-fold preference for r5-HT1B (K-i = 47 +/- 5 nM; n = 3) vs bovine 5-HT1B (K-i = 630 nM; n = 1) receptors. The compound had very low affinity for other monoaminergic receptors examined. The r5-HT1B receptor antagonism was demonstrated by the potentiation of the K+-stimulated release of [H-3]-5-HT from superfused rat brain slices in vitro, an effect that was antagonized by addition of 5-HT to the superfusion fluid. (R)-25 at 20 mg/kg sc enhanced the 5-HT turnover in four rat brain regions (hypothalamus, hippocampus, striatum, and frontal cortex) with about 40% measured as the 5-HTP accumulation after decarboxylase inhibition with 3-hydroxybenzylhydrazine. At 3 mg/kg sc (R)-25 produced a significant increase in the number of wet dog shakes in rats, a 5-HT2A/5-HT2C response that was abolished by depletion of 5-HT after pretreatment with the tryptophan hydroxylase inhibitor p-chlorophenylalanine. These observations show that (R)-25, by inhibiting terminal r5-HT1B autoreceptors, increases the 5-HT turnover and the synaptic concentration of 5-HT.