(+)-4-hydroxy-1-tetralone | 359013-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+)-4-hydroxy-1-tetralone
• 英文别名: (4S)-4-hydroxy-α-tetralone；1(2H)-Naphthalenone, 3,4-dihydro-4-hydroxy-, (4S)-；(4S)-4-hydroxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 359013-54-0
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: BGPJTIXJFAGUIF-VIFPVBQESA-N

物化性质

• 沸点：
  314.7±31.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯甲酰氯 、 (+)-4-hydroxy-1-tetralone 在 吡啶 、 4-二甲氨基吡啶 作用下， 以85%的产率得到4-O-(3,4,5-trimethoxybenzoyl)-α-hydroxytetralone
  参考文献：
  名称：

  Anti-tubercular agents from Ammannia baccifera (Linn.)

  摘要：

  Ammannia baccifera is an important component of various traditional Chinese herbal formulations. The samples of A. baccifera were extracted with methanol and the methanolic extract was successively fractionated with n-hexane, chloroform and n-butanol. The serial chromatographic separation of chloroform and n-butanol fractions resulted in the isolation and characterization of betulinic acid (1), 4-hydroxy-alpha-tetralone (2), tetralone-4-O-beta-D-glucopyranoside (3) and ellagic acid (4). Further, the compound 2 was chemically modified into its five semi-synthetic acyl and aryl derivatives (2A-2E) namely; 4-O-m-anisoyl-alpha-tetralone (2A), 4-O-benzoyl-alpha-tetralone (2B), 4-O-palmitoyl-alpha-tetralone (2C), 4-O-(3,4,5-trimethoxybenzoyl)-alpha-tetralone (2D) and 4-O-myricitoyl-alpha-tetralone (2E). The tetralone group compounds 2, 3 and semi-synthetic derivatives 2A-2E were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv by BACTEC-460 radiometric susceptibility assay. The compounds 2 and 2E have shown significant anti-tubercular activity (MIC 50 mu g/ml) while 2B was moderate active (MIC 100 mu g/ml) against the pathogen. The results of SAR study indicated that substitutions in alpha hydroxyl group of 4-hydroxy-alpha-tetralone either retards or have no increasement in in vitro anti-tubercular potential.

  DOI：

  10.1007/s00044-012-9998-9
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘酚 在 4-二甲氨基吡啶 、 potassium permanganate 、 Pseudomonas cepacia lipase 、 magnesium sulfate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 40.25h， 生成 (+)-4-hydroxy-1-tetralone
  参考文献：
  名称：

  Efficient enzymatic kinetic resolution of 4-hydroxytetralone and 3-hydroxyindanone

  摘要：

  Both enantiomers of 4-acetoxy- and 4-hydroxytetralone have been obtained with high enantiomeric purity by kinetic resolution using enzymes. 3-Hydroxyindanone was successfully resolved using enzymatic transesterification. The absolute configuration of the products were established by literature precedence. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00404-9

文献信息

• Unprecedented Role of Hydronaphthoquinone Tautomers in Biosynthesis
  作者：Syed Masood Husain、Michael A. Schätzle、Steffen Lüdeke、Michael Müller

  DOI：10.1002/anie.201404560

  日期：2014.9.8

  unexpected 1,4‐diketo tautomeric form of 2‐hydroxyhydronaphthoquinone as a stable intermediate. Similar 1,4‐diketo tautomers of hydronaphthoquinones were established as products of the NADPH‐dependent enzymatic reduction of other 1,4‐naphthoquinones, and as substrates for different members of the superfamily of short‐chain dehydrogenases. We propose an essential role of hydroquinone diketo tautomers in

  醌和对苯二酚是最常见的细胞辅助因子，氧化还原介体和天然产物。在这里，我们报道了将2-羟基萘醌还原为稳定的氢萘醌的1,4-二酮互变异构形式，以及它们被真菌四羟基萘还原酶进一步还原的情况。非对映异构体和对映异构体的过量非常高，顺式-3,4-二羟基-1。四氢萘酮的高收率不包括中间氢萘醌。用NADPH和NADPD进行的标记实验证实了2-羟基氢萘醌作为稳定的中间体出乎意料的1,4-二酮互变异构形式的形成。类似的1,4-二氢萘醌的互变异构体被认为是NADPH依赖的其他1,4-萘醌的酶促还原产物，并作为短链脱氢酶超家族不同成员的底物。我们提出氢醌二酮互变异构体在生物合成和排毒过程中的重要作用。
• The Palladium-Catalyzed Aerobic Kinetic Resolution of Secondary Alcohols: Reaction Development, Scope, and Applications
  作者：David C. Ebner、Jeffrey T. Bagdanoff、Eric M. Ferreira、Ryan M. McFadden、Daniel D. Caspi、Raissa M. Trend、Brian M. Stoltz

  DOI：10.1002/chem.200902172

  日期：2009.12.7

  and tert‐butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23 °C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good‐to‐excellent

  已经开发出第一个钯催化的仲醇对映选择性氧化反应，利用容易获得的二胺（-）-金雀花石作为手性配体，分子氧作为化学计量氧化剂。关于碱基和氢键供体作用的机制见解导致了对原始系统的一些改进。也就是说，碳酸铯和叔丁醇的添加大大提高了反应速率，促进了快速分辨率。使用氯仿作为溶剂允许在 23 °C 下使用环境空气作为终端氧化剂，从而提高催化剂选择性。这些改进的反应条件使得能够以良好至优异的选择性因子成功地将苄基、烯丙基和环丙基仲醇动力学拆分为高对映体过量。该催化剂体系也已应用于内消旋二醇的去对称化，提供高产率的对映体富集的羟基酮。
• The Palladium-Catalyzed Oxidative Kinetic Resolution of Secondary Alcohols with Molecular Oxygen
  作者：Eric M. Ferreira、Brian M. Stoltz

  DOI：10.1021/ja015791z

  日期：2001.8.1

  The oxidation of secondary alcohols is one of the most common and well-studied reactions in chemistry. Although excellent catalytic enantioselective methods exist for a variety of oxidation processes, such as epoxidation, dihydroxylation, and aziridination, it is surprising that there are relatively few catalytic enantioselective examples of the ubiquitous alcohol oxidation. In connection with a general

  仲醇的氧化是化学中最常见和研究最充分的反应之一。尽管对于各种氧化过程（例如环氧化、二羟基化和氮丙啶化）存在出色的催化对映选择性方法，但令人惊讶的是，无处不在的醇氧化的催化对映选择性实例相对较少。结合处理新催化氧化系统发现的一般程序，我们在此介绍了使用分子氧作为末端氧化剂的仲醇催化氧化动力学拆分的开发（参见方案 1）。
• Efficient Enantioselective Syntheses of Sertraline, 2-Epicatalponol and Catalponol from Tetralin-1,4-dione
  作者：Alvaro Enriquez Garcia、Souad Ouizem、Xin Cheng、Patrick Romanens、E. Peter Kündig

  DOI：10.1002/adsc.201000384

  日期：2010.9.10

  2]oxazaborole as catalyst to give enantiomerically highly enriched 4‐hydroxy‐1‐tetralone (99% ee) in an efficient one‐pot procedure. The R‐enantiomer provided a rapid access to sertraline while the S‐enantiomer was converted into 2‐epicatalponol and catalponol. A more selective enantioselective route to the antithermitic catalponol made use of the planar chiral tricarbonylchromium complex of hydroxytetralone. Its

  在存在3,3-二苯基-1-丁基四氢-3 H-吡咯并[1,2- c ] [ 1,2,3 ]的情况下，儿茶酚硼烷可还原稳定的二羟基萘互变异构体Tetralin-1,4-dione [1,2- c ] [1,3,2]草a硼烷为催化剂，可通过高效的一锅法制得对映体高度富集的4-羟基-1-丁酮（99％ee）。的[R -对映体提供给舍曲林快速访问而小号-对映体转化为2- epicatalponol和catalponol。通过使用羟基四氢萘酮的平面手性三羰基铬配合物，可以更选择性地对映抗对苯二酚的对映选择性。它的前体铬（三羰基）[η 6得到-四氢化萘-5,8-二酮（1-4,4a，8α）]通过使用三（三羰基）-三（氨）铬和三氟化硼醚化物作为铬（三羰基）片段的源直接络合1,4-二羟基萘。最好在四胺配体存在的情况下进行烯醇盐的烯丙基化反应。最初获得的四氢萘酮配合物中带有异戊二烯基的立体异构中心的完全转化是通过烯醇化形成然后进行质子化实现的。
• CH-activating oxidative hydroxylation of 1-tetralones and related compounds with high regio- and stereoselectivity
  作者：Gheorghe-Doru Roiban、Rubén Agudo、Adriana Ilie、Richard Lonsdale、Manfred T. Reetz

  DOI：10.1039/c4cc04925j

  日期：——

  Mutants of P450-BM3 evolved by directed evolution are excellent catalysts in the CH-activating oxidative hydroxylation of 1-tetralone derivatives and of indanone, with unusually high regio- and enantioselectivity being observed.

  P450-BM3的突变体通过定向进化进化而来，在1-四氢萘衍生物和茚酮的CH活化氧化羟基化反应中是优秀的催化剂，观察到异常高的位置选择性和对映选择性。