3-methyltetrahydro-4H-thiopyran-4-one | 84583-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 3-methyltetrahydro-4H-thiopyran-4-one
• 英文别名: 3-methyl-4-thianone；3-methylthian-4-one；3-methyldihydro-2H-thiopyran-4(3H)-one；3-methyl-tetrahydro-thiopyran-4-one；3-Methyl-tetrahydro-thiopyran-4-on
• CAS: 84583-08-4
• 化学式: C₆H₁₀OS
• 分子量: 130.211
• InChiKey: RYXJDUOHUJITMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyltetrahydro-4H-thiopyran-4-one 在 sodium azide 、 三氯乙酸 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 88.0h， 生成 3-methyl-4-(2-thienyl)tetrahydro-2H-thiopyran-4-azide
  参考文献：
  名称：

  The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum

  摘要：

  With the aim of obtaining selective ligands of the low affinity binding sites of [H-3]-1-[1-(2-thienyl) cyclohexyl] piperidine ([H-3]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [H-3]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the Lipophilicity and modifying the hetero-aromatic moiety yielded some Ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [H-3]TCP in the rat cerebellum. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80046-4
• 作为产物：
  描述：

  3-Carbomethoxy-3-methyltetrahydrothiopyran-4-one 在 硫酸 作用下， 以 水 为溶剂， 反应 19.0h， 以64%的产率得到3-methyltetrahydro-4H-thiopyran-4-one
  参考文献：
  名称：

  Enzymes in organic synthesis. 27. Horse liver alcohol dehydrogenase-catalyzed oxidoreductions of 3-alkylthiopyran ketones and alcohols

  摘要：

  DOI：

  10.1021/jo00154a007

文献信息

• Phencyclidine derivatives, preparation method and pharmaceutical compositions containing same
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06342511B1

  公开（公告）日：2002-01-29

  The invention concerns novel phenylcyclidine derivatives with selective affinity for low affinity receptors, methods for preparing them, pharmaceutical compositions containing them and their use as protective agents for central or peripheral nervous system cells against acute or chronic degeneration, or as an anticonvulsant.

  这项发明涉及具有选择性亲和力的新型苯环丙胺衍生物，以及用于制备它们的方法、含有它们的药物组合物，以及它们作为中枢或外周神经系统细胞的保护剂对抗急性或慢性退化，或作为抗癫痫药物的用途。
• Construction of Stereogenic α,α-Disubstituted Cycloalkanones via 1° Amine Thiourea Dual Catalysis: Experimental Scope and Computational Analyses
  作者：Jun Yong Kang、Ryne C. Johnston、Kevin M. Snyder、Paul Ha-Yeon Cheong、Rich G. Carter

  DOI：10.1021/acs.joc.6b00280

  日期：2016.5.6

  with a ketone containing pre-existing stereocenters has been demonstrated. Computational analyses of the reaction mechanism are reported. In concert with kinetic isotope effect (KIE) experiments, these computational results provide a detailed understanding of the likely mechanism, including the aspects of the organocatalyst scaffold that are critical for stereoselectivity.

  通过利用双功能1°胺硫脲催化剂体系，对有机催化的不对称Pfau-d'Angelo反应进行了机理探索和扩展的实验讨论。在环状酮部分和α，β-不饱和亲电体上都证明了底物范围的显着宽度。已经证明了使用含有预先存在的立体中心的酮来探索该方法的匹配和不匹配选择性。报告了反应机理的计算分析。与动力学同位素效应（KIE）实验相结合，这些计算结果对可能的机理提供了详细的了解，包括对立体选择性至关重要的有机催化剂支架方面。
• Carbon Acid Induced Mukaiyama Aldol Type Reaction of Sterically Hindered Ketones
  作者：Hikaru Yanai、Yasuhiro Yoshino、Arata Takahashi、Takeo Taguchi

  DOI：10.1021/jo100915e

  日期：2010.8.6

  Brønsted acid precatalysts for the Mukaiyama aldol type reactions of sterically hindered ketones. By using Tf2CHCH2CHTf2 in a range from 0.5 to 2.0 mol %, the vinylogous Mukaiyama aldol reaction of α-substituted cyclohexanones with 2-silyloxyfurans smoothly proceeded to give the aldol products in excellent yield without the loss of diastereoselectivity. Under similar conditions, acyclic ketene silyl acetals

  1,1,3,3-四（三氟甲磺酰基）丙烷（Tf 2 CHCH 2 CHTf 2）是对位阻酮的Mukaiyama aldol型反应最有效的布朗斯台德酸预催化剂之一。通过使用0.5〜2.0摩尔％的Tf 2 CHCH 2 CHTf 2，α-取代的环己酮与2-甲硅烷基氧呋喃的乙烯基类Mukaiyama aldol反应平稳地进行，从而以优异的收率得到了aldol产物，而没有非对映选择性的损失。在类似条件下，无环烯酮甲硅烷基缩醛也可作为对位阻酮的亲核试剂。这些发现表明，Tf 2 CHCH 2 CHTf 2 诱导的Mukaiyama aldol型反应可以克服反应位点之间的空间位阻。
• Enzymes in organic synthesis. 28. Reinvestigation of the horse liver alcohol dehydrogenase-catalyzed reductions of 2-alkylcyclohexanones.Identification of <i>cis</i>-alkylcyclohexanols as minor products
  作者：J. Bryan Jones、Tetsuo Takemura

  DOI：10.1139/v82-423

  日期：1982.12.1

  The formation of cis-2-alkylcyclohexanol products from horse liver alcohol dehydrogenase-catalyzed reductions of 2-alkylcyclohexanones has been detected for the first time. The cis-alcohols are minor (<4%) products, with the isomeric trans-products being heavily predominant under all conditions. cis-Alcohol production can be suppressed by suitable manipulation of the reaction conditions. Exclusive

  首次检测到由马肝醇脱氢酶催化还原 2-烷基环己酮生成顺式-2-烷基环己醇产物。顺式醇是次要的 (<4%) 产物，异构反式产物在所有条件下都占主导地位。顺式醇的产生可以通过适当操作反应条件来抑制。通过在适当的缓冲液（如 Tris-HCl）中在最低 [E]/[S] 和可能的 pH 条件下操作，并通过最大限度地减少反应时间，有利于反式醇的完全形成。结果与先前用类似的 3-烷基四氢噻喃-4-one 底物观察到的顺式醇形成相似。
• Preparation of 3-Substituted 4-Thianones and Their 1,1-Dioxides via Palladium Mediated Deallyloxycarbonylation
  作者：Guy Casy、Alan G. Sutherland、Richard J. K. Taylor、Peter G. Urben

  DOI：10.1055/s-1989-27389

  日期：——

  3-Alkyl-4-thianones 4 (3-alkyl-thiacyclohexan-4-ones) can be conveniently prepared by the alkylation of 3-allyloxycarbonyl-4-thianone (1b) followed by deallyloxycarbonylation mediated by tetrakis (triphenylphosphine)palladium in the presence of morpholine. The corresponding sulphones 9, as well as 2,3-dialkyl 4-thianone derivatives 12 and 13 can be prepared by analogous procedures.

  3- 烷基-4-噻酮 4（3-烷基-硫杂环己烷-4-酮）可以通过 3-烯丙氧羰基-4-噻酮（1b）的烷基化，然后在吗啉存在下，由四（三苯基膦）钯介导的脱烯丙氧羰基化反应方便地制备。相应的砜类化合物 9 以及 2,3-二烷基 4-噻酮衍生物 12 和 13 可通过类似的方法制备。

表征谱图