5-methoxy-2-methyl-3-(phenylthio)-1H-indole | 98055-12-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-methoxy-2-methyl-3-(phenylthio)-1H-indole
• 英文别名: 5-methoxy-2-methyl-3-(phenylthio)indole；5-Methoxy-2-methyl-3-phenylthioindole；5-methoxy-2-methyl-3-phenylsulfanyl-1H-indole
• CAS: 98055-12-0
• 化学式: C₁₆H₁₅NOS
• 分子量: 269.367
• InChiKey: YQZWMBRAVOHQGU-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  437.7±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-methyl-3-(phenylthio)-1H-indole 在 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 1.5h， 以96%的产率得到5-甲氧基-2-甲基吲哚
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.

  DOI：

  10.1021/jo00100a045
• 作为产物：
  描述：

  4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenol 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.17h， 生成 5-methoxy-2-methyl-3-(phenylthio)-1H-indole
  参考文献：
  名称：

  A novel efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions

  摘要：

  一种通过醌单-O,S-乙缩醛芳构化诱导硫醚化的新型方法被报道出来。

  DOI：

  10.1039/a702912h

文献信息

• Visible-light promoted synthesis of 3-arylthioindoles from indoles and diaryl disulfides
  作者：Lin-miao Ye、Jie Chen、Peng Mao、Xue-jing Zhang、Ming Yan

  DOI：10.1016/j.tetlet.2017.05.090

  日期：2017.7

  3-Arylthioindoles could be synthesized in good yields via the photoirradiation of indoles and disulfides. The reaction is efficiently promoted by the catalytic amount of sodium iodide. A reaction mechanism involving the electrophilic substitution of indoles with arylsulfenyl iodine intermediates is suggested.

  可以通过吲哚和二硫化物的光辐射以高收率合成3-芳硫基吲哚。催化量的碘化钠可有效地促进反应。提出了涉及用芳基亚硫基碘中间体亲电取代吲哚的反应机理。
• Palladium-Catalyzed Oxidative Sulfenylation of Indoles and Related Electron-Rich Heteroarenes with Aryl Boronic Acids and Elemental Sulfur
  作者：Jianxiao Li、Chunsheng Li、Shaorong Yang、Yanni An、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b01428

  日期：2016.9.2

  An efficient and convenient palladium-catalyzed C–H bond oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur has been described. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting

  已经描述了一种有效且方便的钯催化的吲哚和相关的富电子杂芳烃与芳基硼酸和元素硫的C-H键氧化亚磺酰化反应。该方法提供了一种有用且直接的方法，用于从简单易得的起始原料中以中等至极好的收率组装各种结构多样的3-亚硫基杂芳烃。此外，该合成方案适用于N-保护的和未保护的吲哚。值得注意的是，这一转换也一步完成了两个C–S键的构建。
• Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation
  作者：Haonan Xiang、Jie Liu、Jieping Wang、Lvqi Jiang、Wenbin Yi

  DOI：10.1021/acs.orglett.1c03813

  日期：2022.1.14

  A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barrier in the first step of deoxygenation. The mild deoxygenation process enables the reduction of a wide range of functionalized sulfonyl chlorides

  报道了一种通过协同 CTAB 和方酸促进的磺酰基衍生物脱氧对亲核试剂进行亲电（氟烷基）亚磺酰化的方法。机理研究表明，方酸在脱氧的第一步中显着降低了能量屏障。温和的脱氧过程能够还原多种功能化磺酰氯以及磺酸酐。这种新方法代表了一种使用现成试剂的操作简单的协议，并表现出广泛的官能团耐受性。
• Facile and Efficient Sulfenylation Method Using Quinone Mono-<i>O,S</i>-Acetals under Mild Conditions
  作者：Masato Matsugi、Kenji Murata、Kentoku Gotanda、Hisanori Nambu、Gopinathan Anilkumar、Keita Matsumoto、Yasuyuki Kita

  DOI：10.1021/jo001710q

  日期：2001.4.1

  A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.
• Development of a Novel, Highly Efficient Halide-Catalyzed Sulfenylation of Indoles
  作者：Matthew Tudge、Minoru Tamiya、Cecile Savarin、Guy R. Humphrey

  DOI：10.1021/ol052615c

  日期：2006.2.1

  The reaction of a variety of indoles with N-thioalkyl- and N-thioarylphthalimides to produce 3-thioindoles is reported. Catalytic quantities of halide-containing salts are crucial to the success of this reaction. This highly efficient reaction provides sulfenylated indoles from bench-stable, readily available starting materials in good to excellent yields.