3-甲氧基-5,6,7,8-四氢萘-2-甲醛 | 78112-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 3-甲氧基-5,6,7,8-四氢萘-2-甲醛
• 英文名称: 3-methoxy-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde
• 英文别名: 6-methoxy-1,2,3,4-tetrahydronaphthalene-7-carbaldehyde；7-methoxy-1,2,3,4-tetrahydro-6-naphthaldehyde；5,6,7,8-tetrahydro-2-methoxynaphthalene；3-methoxy-5,6,7,8-tetrahydro-[2]naphthaldehyde；3-Methoxy-5,6,7,8-tetrahydro-[2]naphthaldehyd
• CAS: 78112-35-3
• 化学式: C₁₂H₁₄O₂
• mdl: MFCD07186468
• 分子量: 190.242
• InChiKey: MGPYTUGHWZINMT-UHFFFAOYSA-N

物化性质

• 熔点：
  51-53 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  219-220 °C(Press: 38 Torr)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2912499000

反应信息

• 作为反应物：
  描述：

  3-甲氧基-5,6,7,8-四氢萘-2-甲醛 在 dirhodium tetraacetate 、 sodium tetrahydroborate 、 sodium ethanolate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 55.83h， 生成 1-benzyl-2-(1-hydroxyethyl)-4-methoxy-6,7,8,9-tetrahydro-1H-benz[g]indole
  参考文献：
  名称：

  Carbocyclic[g]indole Inhibitors of Human Nonpancreatic s-PLA₂

  摘要：

  A vinyl azide cyclization method was used to synthesize three different carbocyclic[g]indole scaffolds as inhibitors of human nonpancreatic secretory phospholipase A(2). Each scaffold demonstrated potent enzyme activity in a chromogenic assay system, with select examples also demonstrating potent activity in a secondary DOC/PC assay. Compound 11, representative of the cyclopent[g]indole series, gave an IC50 of 10 nM for the inhibition of hnps-PLA(2) in the chromogenic assay.

  DOI：

  10.1021/jm0401309
• 作为产物：
  描述：

  5,6,7,8-四氢-2-萘酚 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-甲氧基-5,6,7,8-四氢萘-2-甲醛
  参考文献：
  名称：

  Photochemistry of stilbenes. 8. Eliminative photocyclization of o-methoxystilbenes

  摘要：

  DOI：

  10.1021/jo00280a032

文献信息

• [EN] PYRIMIDINE DERIVATIVES AS PGE2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE PYRIMIDINE UTILISÉS EN TANT QUE MODULATEURS DES RÉCEPTEURS DES PGE2
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2018210988A1

  公开（公告）日：2018-11-22

  The present invention relates to pyrimidine derivatives of formula (I) wherein (R1)n, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (II) and their use as pharmaceuticals, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及式(I)的嘧啶衍生物，其中(R1)n，R3，R4a，R4b，R5a，R5b和Ar1如描述中所述，以及它们通过调节免疫反应，包括肿瘤中免疫系统的再激活，用于治疗癌症。本发明进一步涉及新颖的苯并呋喃和苯并噻吩衍生物式(II)，及其作为药物的使用，其制备，药用可接受的盐，及其作为药物的使用，以及包含式(I)中一个或多个化合物的药物组合物，尤其是它们作为前列腺素2受体EP2和/或EP4的调节剂的使用。
• Novel spla2 inhibitors
  申请人：——

  公开号：US20040077704A1

  公开（公告）日：2004-04-22

  A novel class of cycloalkyl fused indole compounds is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.

  揭示了一类新型的环烷基融合吲哚化合物，以及利用这些化合物抑制sPLA2介导的脂肪酸释放，用于治疗炎症性疾病，如感染性休克。
• Georg kalischer and heinz scheyer
  申请人：——

  公开号：US01807693A1

  公开（公告）日：1931-06-02

  311,208. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). Feb. 6, 1928. Aldehydes; aldazines. - Aldehyde groups are introduced into cyclic compounds containing labile hydrogen atoms, in which other hydrogen atoms may be replaced by halogens or other monovalent substituents, except amino groups, by treatment with formamide or with derivatives thereof in which one of the hydrogen atoms of the amino group is substituted by aryl, and the other by alkyl, aralkyl on aryl, in the presence of an acid condensing agent containing chlorine, such as a chloride or oxychloride of phosphorus or sulphur or aluminium chloride. Suitable cyclic compounds are m-xylene, anthracene, N- ethylcarbazol, pyridine, quinoline, naphthostyril, naphtholethers, naphthalene, thioethers, oxythionaphthenes and anthrone and its nuclear substi. tution products. When using the formyl derivatives of secondary amines and cyclic compounds, such as oxythionaphthene and anthrone, containing in ring combination a methylene group and a Ketonic group capable of reacting in the tautomeric enolic form, chlorinated aldehydic derivatives are obtained, the hydroxyl group of the enolic form being replaced by chlorine. The reaction may be carried out in the presence of indifferent organic solvents. In examples, the following products are obtained, using formylmonomethylaniline and phosphorus oxychloride, in some cases in the presence of benzene : (1) panisaldehyde from anisol, (2) 2-ethoxy-1-naphthaldehyde from #-naphtholethylether, and 1-methoxy-5 : 6 : 7 : 8-tetrahydronaphthalene-4-aldehyde and 2-methoxy-5: 6 : 7 : 8-tetrahydronaphthalene. 1-aldehyde from 1- and 2-methoxy-5: 6 : 7 : 8. tetrahydronaphthalene, (3) anthracene-9-aldehyde from anthracene, and 1: 3-dimethyl-benzene-4- aldehyde from m-xylene, (4) a-chloranthracene-9- aldehyde from a-chloranthracene, and (5) 2- and 4-oxy-1-naphthaldehyde from #- and a-naphthol. In these examples, thionyl or sulphuryl chloride, or aluminium chloride may be used instead of phosphorus oxychloride, and other formylated secondary amines, such as formyldiphenylamine, or formamide, instead of formylmonomethylaniline. In a similar manner, 2: 7-dioxynaphthalene-1-aldehyde is obtained from 2: 7-dioxynaphthalene, 4: 8-dioxynaphthalene-1-aldehyde from 1: 5-dioxynaphthalene, 2-oxynaphthalene-1- aldehyde-3-carboxylic acid and the corresponding anilide from 2: 3-oxynaphthoic acid and its anilide, 2: 5-dimethyl-4-oxybenzaldehyde from pxylenol, 2: 4-dioxybenzaldehyde from resorcinol, and vanillin from guaiacol. In further examples, (6) 4-methyl-6-chlor-3-oxythionaphthene-2-aldehyde is obtained by heating 4-methyl-6-chlor-3- oxythionaphthene with formamide and anhydrous aluminium chloride or phosphorus oxychloride, (7) 6-ethoxy-3-oxythionaphthene-2-aldehyde is similarly obtained from 6-ethoxy-3-oxythionaphthene (8) N-ethylcarbazol is converted into an aldehyde by heating with formylmonomethylaniline and phosphorus oxychloride; pyridine and quinoline also yield aldehydes when similarly treated, and (9) naphthostyrilaldehyde is similarly obtained from naphthostyril. In further examples, in which chlorine is introduced at the same time as the aldehyde group, (10) 3-chlor-6-ethoxythionaphthene-2-aldehyde is obtained by treating 6. ethoxy-3-oxythionaphthene with formylmonomethylaniline and phosphorus oxychloride; 4- methyl-6-chlor-3-oxythionaphthene when similarly treated yields 4-methyl 3: 6 - dichlorthionaphthene-2-aldehyde, and (11) anthrone, when treated with formylmonomethylaniline or formyl. diphenylamine and phosphorus oxychloride yields 9-chloranthracene-10-aldehyde; when similarly treated, 2-chloranthrone yields 3: 10-dichloranthracene-9-aldehyde, 1 : 5-dichloranthrone yields 1: 5: 10-trichloranthracene-9-aldehyde, and desoxy-alizarine-dimethylether yields 1: 2-dimethnxy-lO-chloranthracene-9-nldehyde. The aldazines of most of the products are described.

  311,208. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). Feb. 6, 1928. 醛类化合物；醛肼。- 醛基被引入含有活泼氢原子的环状化合物中，其中其他氢原子可以被卤素或其他一价取代基（除氨基外）所取代，通过与甲酰胺或其衍生物处理，其中氨基的一个氢原子被芳基取代，另一个被烷基、芳基烷基或芳基取代，存在含氯的酸性缩合剂的情况下进行，如磷或硫或铝氯化物的氯化物或氧氯化物。适合的环状化合物是间二甲苯，蒽，N-乙基咔唑，吡啶，喹啉，萘基苯，萘醚，萘，硫醚，氧硫萘烯和蒽醌及其核取代产物。当使用二级胺和环状化合物的甲酰衍生物，如氧硫萘烯和蒽醌，其中环中组合了一个甲基和一个酮基，能够以互变式烯醇形式反应时，得到氯代醛衍生物，烯醇形式的羟基被氯取代。该反应可在惰性有机溶剂存在下进行。在示例中，使用甲酰单甲基苯胺和磷氧氯化物，在某些情况下，在苯的存在下，得到以下产品：（1）苯甲醛，（2）2-乙氧基-1-萘甲醛，从 #-萘醚，和 1-甲氧基-5:6:7:8-四氢萘-4-甲醛和 2-甲氧基-5:6:7:8-四氢萘烯-1-甲醛从 1-和 2-甲氧基-5:6:7:8-四氢萘烯，（3）蒽-9-甲醛从蒽，和 1:3-二甲基苯-4-甲醛从间二甲苯，（4）α-氯蒽-9-甲醛从α-氯蒽，和（5）2-和 4-氧基-1-萘甲醛从 #-和 α-萘酚。在这些示例中，可以使用亚硫酰氯或硫酰氯，或铝氯化物代替磷氧氯化物，以及其他甲酰化的二级胺，如甲酰二苯胺，或甲酰胺，代替甲酰单甲基苯胺。以类似的方式，从 2:7-二氧基萘烯得到 2:7-二氧基萘烯-1-甲醛，从 1:5-二氧基萘烯得到 4:8-二氧基萘烯-1-甲醛，从 2:3-氧基萘甲酸和其酰胺得到 2-氧基萘烯-1-甲醛-3-羧酸和相应的苯胺，从对甲酚得到 2:5-二甲基-4-氧基苯甲醛，从邻苯二酚得到 2:4-二氧基苯甲醛，从愈创木酚得到香草醛。在进一步的示例中，（6）4-甲基-6-氯-3-氧基硫萘烯-2-甲醛通过加热 4-甲基-6-氯-3-氧基硫萘烯与甲酰胺和无水氯化铝或磷氧氯化物得到，（7）6-乙氧基-3-氧基硫萘烯-2-甲醛同样是通过 6-乙氧基-3-氧基硫萘烯得到（8）N-乙基咔唑通过与甲酰单甲基苯胺和磷氧氯化物加热转化为醛；吡啶和喹啉同样在类似处理时产生醛，（9）萘基苯甲醛同样是从萘基苯甲醛中得到。在进一步的示例中，同时引入氯和醛基时，（10）3-氯-6-乙氧硫萘烯-2-甲醛通过处理 6-乙氧基-3-氧基硫萘烯与甲酰单甲基苯胺和磷氧氯化物得到；4-甲基-6-氯-3-氧基硫萘烯在类似处理时产生 4-甲基-3:6-二氯硫萘烯-2-甲醛，以及（11）蒽醌，当与甲酰单甲基苯胺或甲酰二苯胺和磷氧氯化物处理时得到 9-氯蒽-10-甲醛；类似处理时，2-氯蒽醌得到 3:10-二氯蒽-9-甲醛，1:5-二氯蒽醌得到 1:5:10-三氯蒽-9-甲醛，去氧基紫嫣甲醛二甲醚得到 1:2-二甲氧-10-氯蒽-9-醛。大多数产品的醛肼已被描述。
• Process For Preparation Of Acetals
  申请人：RELIANCE INDUSTRIES LIMITED

  公开号：US20130296580A1

  公开（公告）日：2013-11-07

  A process for the preparation of 1,3:2,4-bis (4-methylbenzylidene) sorbitol (MDBS) and 1,3:2,4-bis (3,4-dimethylbenzylidene) sorbitol (DMDBS) via a dehydrocondensation reaction is disclosed. The reaction is carried out between an aldehyde and an alditol in a mole ratio of 2:1 wherein ionic fluid is used as the acidic catalyst and/or reaction medium. The ionic fluid used in accordance with the present invention is quaternary ammonium salt based ionic liquid.

  本发明揭示了一种通过脱水缩合反应制备1,3:2,4-双(4-甲基苯基亚甲基)山梨醇(MDBS)和1,3:2,4-双(3,4-二甲基苯基亚甲基)山梨醇(DMDBS)的方法。该反应在醛和醇糖的摩尔比为2:1的条件下进行，其中离子液体被用作酸性催化剂和/或反应介质。本发明所使用的离子液体是基于季铵盐的离子液体。
• Process For The Preparation of Alditol Acetals
  申请人：RELIANCE INDUSTRIES LIMITED

  公开号：US20130296581A1

  公开（公告）日：2013-11-07

  The present invention is directed to a process for the preparation of 1,3:2,4-bis (4-methylbenzylidene) sorbitol (MDBS) and 1,3:2,4-bis (4-dimethylbenzylidene) sorbitol (DMDBS) by dehydrocondensating an aldehyde and an alditol using a hydrophobic ionic liquid as an acid catalyst. The ionic liquid used in the accordance with the process of the present invention is a phosphonium ion based ionic liquid.

  本发明涉及使用疏水性离子液体作为酸催化剂，通过脱氢缩合醛和糖醇的方法制备1,3:2,4-双(4-甲基苯亚甲基)山梨醇（MDBS）和1,3:2,4-双(4-二甲基苯亚甲基)山梨醇（DMDBS）的过程。本发明所使用的离子液体是以磷离子为基础的离子液体。