6-chloro-3-(phenylthio)-1H-indole | 92161-72-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-chloro-3-(phenylthio)-1H-indole
• 英文别名: 6-chloro-3-phenylsulfanyl-1H-indole
• CAS: 92161-72-3
• 化学式: C₁₄H₁₀ClNS
• 分子量: 259.759
• InChiKey: WTHWMHJTNMQVFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chloro-3-(phenylthio)-1H-indole 在 Oxone 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 生成 3-(benzenesulfonyl)-6-chloro-1H-indole
  参考文献：
  名称：

  1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-indoles as novel 5-HT6 receptor ligands

  摘要：

  Novel 1-(2-aminoethyl)-3-(arylsulfonyl)-1H-indoles were prepared. Binding assays indicated they are 5-HT6 receptor ligands, among which N,N-dimethyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8t and N-methyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8u showed high affinity for 5-HT6 receptors with K-i = 3.7 and 5.7nM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.003
• 作为产物：
  描述：

  6-氯吲哚 、 苯硫酚 在 碘 、 potassium iodide 作用下， 以 乙醇 为溶剂， 生成 6-chloro-3-(phenylthio)-1H-indole
  参考文献：
  名称：

  1-(2-Aminoethyl)-3-(arylsulfonyl)-1H-indoles as novel 5-HT6 receptor ligands

  摘要：

  Novel 1-(2-aminoethyl)-3-(arylsulfonyl)-1H-indoles were prepared. Binding assays indicated they are 5-HT6 receptor ligands, among which N,N-dimethyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8t and N-methyl-N-{2-[3-(1-naphthylsulfonyl)-1H-indol-1-yl]ethyl}amine 8u showed high affinity for 5-HT6 receptors with K-i = 3.7 and 5.7nM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.003

文献信息

• Iodine-Catalyzed Regioselective Sulfenylation of Indoles with Sulfonyl Hydrazides
  作者：Fu-Lai Yang、Shi-Kai Tian

  DOI：10.1002/anie.201301437

  日期：2013.4.26

  New S in town: Sulfonyl hydrazides smoothly undergo sulfenylation with indoles in the presence of 10 mol % I2 to give structurally diverse indole thioethers in moderate to excellent yields with extremely high regioselectivity. This study paves the way for the use of sulfonyl hydrazides as unique sulfur electrophiles in chemical synthesis.

  城镇中的新S：磺酰肼在10 mol％I 2的存在下与吲哚平稳地进行亚磺酰基化反应，以中等至优异的收率以极高的区域选择性提供结构多样的吲哚硫醚。这项研究为磺酰肼在化学合成中用作独特的硫亲电试剂铺平了道路。
• 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。
• Byproduct promoted regioselective sulfenylation of indoles with sulfinic acids
  作者：Cong-Rong Liu、Liang-Hui Ding

  DOI：10.1039/c4ob02575j

  日期：——

  An unprecedented method to synthesise 3-sulfenylindoles is demonstrated via byproduct promoted sulfenylation of indoles with sulfinic acids.

  展示了一种前所未有的合成3-磺基吲哚的方法，即通过副产物促进的吲哚与亚砜酸的磺化反应。
• Recyclable Cellulose-Derived Fe3O4@Pd NPs for Highly Selective C–S Formation by Heterogeneously C–H Sulfenylation of Indoles
  作者：Shengyi Li、Jinguo Wang、Jianzhong Jin、Jianying Tong、Chao Shen

  DOI：10.1007/s10562-020-03144-9

  日期：2020.8

  An efficient and convenient method was developed for the preparation of 3-sulfenylindoles via a cellulose-derived Fe3O4@Pd NPs catalyzed heterogeneously C–H sulfenylation of indoles. This approach provides an effective synthetic route to an important class of indoles derivatives and features high efficiency, easy operation, good practicality, and environmental friendliness. The recoverable catalyst

  通过纤维素衍生的 Fe3O4@Pd NPs 催化吲哚的非均相 C-H 磺基化，开发了一种有效且方便的方法来制备 3-磺基吲哚。该方法为一类重要的吲哚衍生物提供了一条有效的合成路线，具有高效、易操作、实用性强、环境友好等特点。使用外部磁场将可回收催化剂从反应混合物中分离出来，可循环使用五次，催化性能不会有很大损失。开发了一种通过纤维素衍生的 @Pd NPs 催化吲哚的非均相 C-H 磺基化来制备 3- 磺基吲哚的有效方法。
• CsOH-Promoted Regiospecific Sulfenylation, Selenylation, and Telluration of Indoles in H2O
  作者：Xue-Qiang Wang、Ningbo Li、Shitang Xu、Rongnan Yi、Chunling Zeng、Yue Cui、Xinhua Xu

  DOI：10.1055/a-1879-2521

  日期：2023.1

  Various indole-containing compounds have shown impressive pharmaceutical activities against a variety of diseases. However, the functionalization of indoles usually relies on systems that use organic solvents, which do not meet the criteria for green and sustainable chemical development. To address this issue, regiospecific sulfenylation, selenylation, and telluration of indoles were developed using H2O as solvent. The highly efficient chalcogenylation of indoles was achieved utilizing CsOH as a promoter, thus avoiding the use of expensive transition-metal catalysts. This newly developed protocol is characterized by its outstanding features including simple operation, mild conditions, wide substrate scope, excellent functional group tolerance, and recyclability, leading to the convenient synthesis of 3-chalcogenyl-indoles.

  摘要 各种含吲哚的化合物在治疗多种疾病方面表现出令人印象深刻的药物活性。然而，吲哚的功能化通常依赖于使用有机溶剂的体系，这不符合绿色和可持续化学发展的标准。为解决这一问题，我们以 H2O 为溶剂，开发了吲哚的区域特异性亚硫酰化、硒化和碲化反应。利用 CsOH 作为促进剂实现了吲哚的高效缩醛化，从而避免了使用昂贵的过渡金属催化剂。这一新开发的方案具有操作简单、条件温和、底物范围广、官能团耐受性好和可回收等突出特点，可方便地合成 3-醛基吲哚。