4-甲基-2-硫基苯甲醛 | 294674-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 中文名称: 4-甲基-2-硫基苯甲醛
• 英文名称: p-methyl-mercapto-benzaldehyde
• 英文别名: 4-methyl-2-mercaptobenzaldehyde；4-methylmercaptobenzaldehyde；4-Methyl-2-sulfanylbenzaldehyde
• CAS: 294674-97-8
• 化学式: C₈H₈OS
• 分子量: 152.217
• InChiKey: IOBQGBDPPIJYTD-UHFFFAOYSA-N

物化性质

• 沸点：
  268.5±28.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲基-2-硫基苯甲醛 、 β-amino-β-ethoxyacrylic acid ethyl ester 以 乙醇 为溶剂， 以52%的产率得到2-amino-6-ethoxy-4-(4-methylmercaptophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  2-Amino-4,5-dihydropyridine derivatives and process for their preparation

  摘要：

  6-位置被低烷氧基或低硫代烷基取代的2-氨基-4,5-二氢吡啶-3,5-二羧酸酯，可选地在4-位置被低烷基、苯基、取代苯基或杂环基取代，是抗高血压药物和冠状血管扩张剂。这些化合物通过醛和3-氨基丙烯酸酯（在3-位置带有烷氧基或烷硫基团）的缩合制备，其中2-氨基-4-(3-硝基苯基)-6-乙氧基-4,5-二氢吡啶-3,5-二羧酸二乙酯是代表性实施例。

  公开号：

  US03951993A1

文献信息

• Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction
  作者：Rajasekhar Dodda、Joshua J. Goldman、Tanmay Mandal、Cong-Gui Zhao、Grant A. Broker、Edward R. T. Tiekink

  DOI：10.1002/adsc.200700331

  日期：2008.3.7

  Enantioenriched 2,3,4-trisubstituted thiochromanes have been synthesized by using a cupreine-catalyzed tandem Michael addition-Henry reaction between 2-mercaptobenzaldehydes and beta-nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be further improved through a single recrystallization (up to 98% de and> 99% ee).

  通过使用 2-巯基苯甲醛和 β-硝基苯乙烯之间的铜催化串联迈克尔加成-亨利反应合成了对映体富集的 2,3,4-三取代硫代苯并二氢吡喃。标题化合物获得了良好的非对映选择性和对映选择性，可以通过单次重结晶进一步改进（高达 98% de 和 > 99% ee）。
• 2,3,5,6-Tetracarboxy-1,4-dihydropyridine derivatives
  申请人：Bayer Aktiengesellschaft

  公开号：US03943140A1

  公开（公告）日：1976-03-09

  1,4-Dihydropyridines bearing carboxy functions in the 3-, 5- and 6- or 2-, 3-, 5- and 6-positions and being substituted in the 4-position by phenyl, substituted phenyl, naphthyl, phenylalkyl or a heterocyclic group are antihypertensive agents and coronary vessel dilators. The compounds, of which 2-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5,6-tricarboxylic acid triethylester is a representative embodiment, are prepared through condensation of an enamine with an ylidene acid ester, the latter being separately prepared or prepared in situ.

  3-、5-和6-位上带有羧基的1,4-二氢吡啶以及在4-位被苯基、取代苯基、萘基、苯基烷基或杂环基取代的化合物是抗高血压药物和冠脉血管扩张剂。这些化合物的制备通过烯胺与酸酯亚甲基的缩合反应进行，后者可以单独制备或原位制备，其中2-甲基-4-(3-硝基苯基)-1,4-二氢吡啶-3,5,6-三羧酸三乙酯是一个代表性的实施例。
• Chiral Amine Thiourea-Promoted Enantioselective Domino Michael-Aldol Reactions between 2-Mercaptobenzaldehydes and Maleimides
  作者：Liansuo Zu、Hexin Xie、Hao Li、Jian Wang、Wei Jiang、Wei Wang

  DOI：10.1002/adsc.200700158

  日期：2007.8.6

  An organocatalytic, enantioselective domino Michael-aldol reaction of 2-mercaptobenzaldehydes with maleimides has been developed. The process, catalyzed by a bifunctional chiral amine thiourea via a hydrogen-bonding mediated activation mechanism using as low as 1 mol % catalyst loading, affords versatile succinimide-containing benzothiopyrans with the generation of 3 stereogenic centers in one single

  已经开发了2-巯基苯甲醛与马来酰亚胺的有机催化，对映选择性的多米诺迈克尔-醛醇缩合反应。该方法由双官能手性胺硫脲通过氢键介导的活化机制（使用低至1 mol％的催化剂负载量）进行催化，可在一次操作中生成多功能的含琥珀酰亚胺的苯并硫吡喃，并生成3个立体异构中心。
• Facile synthesis of thiochromanyl-spirooxindoles via K 2 CO 3 catalyzed tandem sulfa-Michael/Aldol reaction
  作者：Zhou Sun、Shuangshang Tian、Shilin Li、Yun Liu、Yuan Zhang、Ying Li

  DOI：10.1016/j.tetlet.2017.07.033

  日期：2017.8

  A facile method for the synthesis of thiochromanyl-spirooxindoles via sulfa-Michael/Aldol reaction of 3-ylideneoxindoles with thiosalicylaldehydes has been developed. This tandem reaction, which tolerates a wide variety of functional groups, furnished diverse substituted functional thiochromanyl-spirooxindoles in up to 90% yields with good diastereoselectivities. Furthermore, the reaction system could

  已经开发了一种通过3-亚硝基氧吲哚与硫代水杨醛的磺胺-迈克尔/阿尔道反应合成硫代苯并二氢吡喃基-螺并氧杂多环的简便方法。这种串联反应可耐受多种官能团，可提供高达90％的产率和良好的非对映选择性，从而取代了各种取代的官能团硫代苯并吡喃基-螺并氧杂吲哚。此外，在温和的条件下，该反应体系可以有效地促进至克级。
• Construction of Chiral Isotetronic Acid-Fused Thiochromane via Doubly Annulative Strategy
  作者：Yiran Mo、Xuehuan Zhang、Yongqi Yao、Cong Duan、Ling Ye、Zhichuan Shi、Zhigang Zhao、Xuefeng Li

  DOI：10.1021/acs.joc.0c02878

  日期：2021.3.19

  ctonization cascade reaction has been established to construct isotetronic acid-fused thiochromanes in a highly stereoselective fashion (≥11:1 dr, 35–98% ee). The tricyclic products were obtained in 35–99% isolated yields in the presence of a bifunctional squaramide. Three reactive sites of β,γ-unsaturated α-ketoester, including the less-explored ester carbonyl group, were sequentially utilized to

  已经建立了磺胺-迈克尔/羟醛/内酯化级联反应，以高度立体选择性的方式（≥11：1 dr，35-98％ee）构建等渗酸融合的硫代苯并二氢吡喃。在双功能方酰胺存在下，三环产物的分离产率为35–99％。β，γ-不饱和α-酮酸酯的三个反应位点，包括未开发的酯羰基基团，可通过一锅操作依次用于构建两个稠合的杂环。