2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚-1-硫酮 | 91091-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚-1-硫酮
• 英文名称: 2,3,4,9-tetrahydro-1H-β-carboline-1-thione
• 英文别名: 2,3,4,9-tetrahydro-β-carboline-1-thione；3,4-dihydro-2H-β-carboline-1-thione；Ycyysganhbdbsn-uhfffaoysa-；2,3,4,9-tetrahydropyrido[3,4-b]indole-1-thione
• CAS: 91091-03-1
• 化学式: C₁₁H₁₀N₂S
• 分子量: 202.28
• InChiKey: YCYYSGANHBDBSN-UHFFFAOYSA-N

物化性质

• 沸点：
  406.0±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚-1-硫酮 在 sodium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 28.0h， 生成 methyl 2-((4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)amino)benzoate
  参考文献：
  名称：

  生物活性生物碱芸香芸香碱，硫氧鸟嘌呤A，脱氧vasicinone及其杂环同系物的简便实用合成

  摘要：

  从适当的芳香族氨基酸7或相应的芳香族氨基酯8或相应的芳香族氨基酯8和亚氨基硫醚5或6中报告了嘧啶β-咔啉1和2的有效组装，包括生物活性生物碱芸香菜碱，硫氧鸟嘌呤A和脱氧vasicinone（3）。一步顺序以中等到良好的产量。该方法的关键步骤基于甲硫基的分子内氮杂置换，然后进行自发的环脱水。此外，当使用芳族氨基酯8代替氨基酸时，发生串联氨基-甲硫基置换/氨基酯环化。

  DOI：

  10.1016/j.tetlet.2006.01.031
• 作为产物：
  描述：

  2-(吲哚-3-基)乙基异硫氰酸酯 在 polyphosphoric acid 作用下， 反应 2.0h， 以99%的产率得到2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚-1-硫酮
  参考文献：
  名称：

  RUTAECARPINE DERIVATIVES FOR ACTIVATING CYP1A2 IN A SUBJECT

  摘要：

  本文提供的教导通常涉及包含路特卡品衍生物的组合物，通过酶诱导激活CYP1A2。这种衍生物的用途可以包括从受试者中去除咖啡因，改善睡眠，治疗失眠，治疗咖啡因中毒，治疗咖啡因成瘾和戒断症状等。咖啡因只是可以使用本文所教导的衍生物去除的底物的一个例子，其他例子，包括茶碱，在本文中也提供了。

  公开号：

  US20120322816A1

文献信息

• Microwave-assisted synthesis of thioamides with elemental sulfur
  作者：Mátyás Milen、Péter Ábrányi-Balogh、András Dancsó、György Keglevich

  DOI：10.1080/17415993.2011.640329

  日期：2012.2.1

  sodium hydrogen sulfide/diethylamine hydrochloride (8) as the reagent. Thioamides have also been prepared from amides, reacting them with tetraphosphorus decasulfide, either with or without additives (9), or using Lawesson’s reagent (10), ethylaluminum sulfide (11), or boron sulfide (12). Another method for the synthesis of thioamides utilizes elemental sulfur in the Willgerodt–Kindler reaction involving

  硫代酰胺是有机化学中有价值的中间体 (1)。此外，该官能团是一些应用广泛的药效团的重要组成部分 (2)。文献中报道了许多制备硫代酰胺的方法。通常，它们是使用硫代乙酸 (3)、O,O-二烷基二硫代磷酸酯 (4)、二苯基膦二硫代酸 (5)、三甲基硅烷硫醇钠 (6)、Dowex SH (7) 或硫化氢钠/二乙胺盐酸盐（8）为试剂。硫代酰胺也已由酰胺与十硫化四磷反应制备，有或没有添加剂 (9)，或使用劳森试剂 (10)、乙基硫化铝 (11) 或硫化硼 (12)。另一种合成硫代酰胺的方法在涉及胺和醛或酮的 Willgerodt-Kindler 反应中利用元素硫 (13)。在过去的几年中，硫作为一种简单、廉价且通用的试剂已被用于许多有机转化中 (14)。我们的目的是研究各种芳基甲胺衍生物在微波 (MW) 条件下与元素硫的反应。
• A short synthesis of (±)-alloyohimbane via a thioisomünchnone based intramolecular dipolar-cycloaddition reaction
  作者：Todd M. Heidelbaugh、Bing Liu、Albert Padwa

  DOI：10.1016/s0040-4039(98)00901-0

  日期：1998.7

  Thioisomunchnone dipoles were generated by the reaction of bromoalkenoyl chlorides with thioamides. The intramolecular dipolar-cycloaddition reaction was used for a short synthesis of the yohimbanoid alkaloid (+/-)-alloyohimbane. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A One-Pot Bicycloannulation Method for the Synthesis of Tetrahydroisoquinoline Systems
  作者：Albert Padwa、L. Scott Beall、Todd M. Heidelbaugh、Bing Liu、Scott M. Sheehan

  DOI：10.1021/jo991742h

  日期：2000.5.1

  A highly effective method for the synthesis of the core indolo[2,3-a]quinolizidine skeleton found in yohimbine is described. The reaction of N-monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomunchnones as transient 1,3-dipoles that undergo ready intramolecular cycloaddition across the tethered pi-bond to give thio-bicycloannulated products in a one-pot operation. The stereochemical outcome of the intramolecular reaction is the consequence of an endo cycloaddition of the neighboring-bond across the transient thioisomunchnone dipole. A major limitation of the method is that when a hydrogen is present in the alpha-position of the thioamide the initially formed thio-N-acyliminium ion undergoes proton loss to produce a S ,N-ketene acetal at a faster rate than dipole formation. Treatment of tetrahydro-beta-carboline-1-thione with 2-bromooct-7-enoyl chloride followed by reductive removal of sulfur from the cycloadduct resulted in the formation of (+/-)-alloyahimbanone. Attempts to cycloadd the thioisomunchnone dipole across several nucleophilic-bonds failed, and instead, products derived from cyclization of the pi-bond onto the initially formed thio-N-acyliminium ion were formed. The resulting N,S-ketals were further converted into several tetrahydroisoquinoline alkaloids in good yield.
• Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders
  作者：Petr Benovsky、John R Stille

  DOI：10.1016/s0040-4039(97)10297-0

  日期：1997.12

  The aza-annulation of enamino ester substrates has been demonstrated as an efficient alternative to the syntheses of non-benzodiazepine sleep inducers. Enamino ester substrates derived from aryl, thiophene, and indole functionality were prepared from the corresponding ethyl amines by isothiocyanate formation followed by acid catalyzed cyclization. (C) 1997 Elsevier Science Ltd.
• Access to substituted thiapyrrolizidinones and fused pyridones using the domino N-acyliminium-thionium equilibrium/1,3-dipolar cycloaddition/desulfurization cyclization cascade
  作者：Abdulkareem Hamid、Hassan Oulyadi、Adam Daïch

  DOI：10.1016/j.tet.2006.04.032

  日期：2006.6

  Substituted thiapyrrolizidinones and fused pyridones, and quinolizinones were reported efficaciously from suitable thioamides in yields ranging from 30% to 65%. The reaction proceeded in a one-pot procedure as cascade process by the intramolecular 1,3-dipolar cycloaddition of thioisomunchnones followed by desulfurization of the adducts. During these investigations, the mechanistic aspects of the process were also discussed. (c) 2006 Published by Elsevier Ltd.

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