CAS: 529-33-9; 1,2,3,4-Tetrahydronaphthalen-1-Ol

该化合物是属于酒精类的有机化合物,其特点是双环结构,特别是四轮框架,由六人组成的芳香环组成,与五人环结合.在与引信环系相邻的碳原子上存在一个氢氧基(-OH)组,将其定义为酒精.1-Tetralol通常没有色,可与有特色的气味的黄色淡色液体无色.它溶于有机溶剂,水中溶解性有限,因为其含水的碳氢化合物结构.该化合物在各种化学应用中,包括作为有机合成的中间体和生产香气和药品,具有兴趣.此外,它可能表现出温和的生物活动,成为医学化学研究的课题.安全数据表明,与许多有机溶剂一样,它处理时应当小心避免吸入或皮肤接触.

结构式图片

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上下游产品

tetralin 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide α-naphthol diethyl ether (+/-)-phthalic acid mono-(1,2,3,4-tetrahydro-[1]naphthyl ester) 1,2-Dihydronaphthalene bis-(1,2,3,4-tetrahydro-1-naphthyl) ether r,8ac)-decahydro-naphthalen-1t-ol(4ar,8ac)-decahydro-naphthalen-1t-ol

合成工艺路线路线简述

  • 合成目标产物 1,2,3,4-Tetrahydro-1-Naphthol 主要起始原料 1-Tetralone
  • (文献来源)合成步骤主要原料 1-Tetralone
1,2,3,4-Tetrahydronaphthalen-1-Ylboronic Acid置于rose Bengal,三乙胺体系中,用 乙醇 作为反应溶剂,化学反应 12.0H,以86%的收率获得产物1,2,3,4-四氢-1-萘酚
参考文献:使用原位产生的过氧化氢的可见光介导的有机氧化合物的好氧氧化
标题:使用原位产生的过氧化氢的可见光介导的有机氧化合物的好氧氧化
摘要:已经开发了一种简单而通用的可见光介导的有机硼化合物的氧化方法,其中孟加拉红作为光催化剂,亚化学计量的et 3 N作为电子给体,而空气作为氧化剂.这种温和且不含金属的方案显示了广泛的底物范围,并以中等至极好的收率提供了多种脂族醇和酚.值得注意的是,该方法的鲁棒性在有机硼化合物的立体有氧氧化中得到了证明.
DOI:10.1021/acs.Orglett.8B02095

海关参考信息

专利信息


专利号:US-5756790-A
优先权日:1995-09-29
标题 :Optically active cobalt (II) complexes and method for the preparation of optically active alcohols
发明人:MUKAIYAMA TERUAKI; YOROZU KIYOTAKA; NAGATA TAKUSHI; YAMADA TORU; SUGI KIYOAKI
权利人:MITSUI PETROCHEMICAL IND
摘要:The invention provides a method for preparing an optically active alcohol comprising the step of reacting a ketone compound with a hydride reagent in the presence of an optically active metal compound. The resulting optically active alcohols are useful as intermediates for the synthesis of physiologically active compounds such as drugs and pesticides, functional materials such as liquid crystals, and raw materials for synthesis in fine chemistry. A novel optically active cobalt (II) complex useful as a catalyst is also provided.

专利号:US-2001044142-A1
优先权日:2000-04-28
标题:Microbial reductase useful for the stereoselective reduction of a racemic tetralone
发明人:BROWN MARIA S; FEDECHKO RONALD W; WONG JOHN W
摘要:The present invention relates to novel compositions of matter comprising an enzyme activity capable of carrying out the following stereoselective reduction of a racemic tetralone: n n n The chiral tetralone can be used in the synthesis of sertraline, well known to be useful, for example, as an antidepressant and anorectic agent, and in the treatment of chemical dependencies, anxiety-related disorders, premature ejaculation, cancer and post-myocardial infarction.

专利号:US-11976021-B2
优先权日:2022-06-27
标 题:Synthesis of tetrahydronaphthalenols and uses thereof
发明人:VULIGONDA VIDYASAGAR
权利人:IO THERAPEUTICS INC
摘要:Provided herein are compounds and synthetic methods useful for preparing tetrahydronaphthalenol derivatives, and uses of the compounds prepared.

专利号:US-6589777-B1
优先权日:1998-10-29
标题:Stereoselective microbial reduction of a racemic tetralone
发明人:MORSE BROOK K; TRUESDELL SUSAN J; WONG JOHN W
权利人:PFIZER
摘要:The present invention relates to processes for carrying out the following stereoselective microbial reduction of a racemic tetralone: n which comprises: contacting a compound of formula (I) with a microorganism, or an enzyme reduction system capable of accomplishing the subject reduction comprising an enzyme derived from said microorganism and a co-factor for said enzyme, and incubating the resulting mixture under conditions sufficient to yield the (4R) tetralol of formula (II) and to leave substantially unreacted the (4S) tetralone of formula (V) or “chiral tetralone.â€? The chiral tetralone can be used in the synthesis of sertraline. The subject process further optionally comprises the separation of the (4S) tetralone of formula (V) from the (4R) tetralol of formula (II). The (4R) tetralol can be recycled to produce the compound of formula (I) and the subject process repeated to result in even more of the desired (4S) tetralone of formula (V).

专利号:US-3699180-A
优先权日:1971-05-26
标题 :Isomerization of dihydronaphthalenes
发明人:WAYWELL DAVID R; WEST CHARLES T
权利人:STANDARD OIL CO
摘要:An improved method for conversion of 1,4-dihydronaphthalene to the corresponding 1,2-dihydro isomer employs as catalyst an alkali metal hydroxide in a polar solvent, preferably isopropyl alcohol. At moderate temperatures, ranging from 60* to 100* C., the 1,2-dihydro isomer is obtained directly in sufficient purity for use in the synthesis of polymers and plastic materials.

专利号:US-6090810-A
优先权日:1995-09-01
标题:Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
发明人:KLEIN ELLIOTT S; JOHNSON ALAN T; STANDEVEN ANDREW M; BEARD RICHARD L; GILLETT SAMUEL J; DUONG TIEN T; NAGPAL SUNIL; VULIGONDA VIDYASAGAR; TENG MIN; CHANDRARATNA ROSHANTHA A
权利人:ALLERGAN SALES INC
摘要:Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity. These assays are based on the ability of negative hormones to down-regulate the activity of chimeric retinoid receptors engineered to possess a constitutive transcription activator domain.
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主要参考文献

[参考文献]: D E Drayer, Et Al. Metabolism Of Tetralin And Toxicity Of Cuprex In Man. Drug Metab Dispos. 1973 May-Jun;1(3):577-9.
[参考文献]: Jonathan J Sheng, Et Al. Influence Of Phenylalanines 77 And 138 On The Stereospecificity Of Aryl Sulfotransferase Iv. Drug Metab Dispos. 2004 May;32(5):559-65.
[参考文献]: Vyas Sharma, Et Al. Comparative Molecular Field Analysis Of Substrates For An Aryl Sulfotransferase Based On Catalytic Mechanism And Protein Homology Modeling. J Med Chem. 2002 Dec 5;45(25):5514-22.

合成参考文献


摘要:Wicha, J., Science of Synthesis, (2009) 48, 166.
摘要:Shimizu, M., Science of Synthesis Knowledge Updates, (2010) 3, 48.
摘要:Brown, J. M.; Nguyen, B. N., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 306.
摘要:Stoltz, B.; Ebner, D. C.; Park, N., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 210.
摘要:Stoltz, B.; Ebner, D. C.; Park, N., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 214.
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