3-(benzylsulfanyl)-2-methyl-1H-indole | 501018-03-7

• 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
• 英文名称: 3-(benzylsulfanyl)-2-methyl-1H-indole
• 英文别名: 3-(benzylthio)-2-methyl-1H-indole；ZINC01869964；2-methyl-3-(phenylmethylthio)-1H-indole；3-benzylsulfanyl-2-methyl-1H-indole
• CAS: 501018-03-7
• 化学式: C₁₆H₁₅NS
• 分子量: 253.368
• InChiKey: LONJHSQLGJHHKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 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：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 二苄基二硫 在 氟硼酸钠 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以72%的产率得到3-(benzylsulfanyl)-2-methyl-1H-indole
  参考文献：
  名称：

  碘化钾介导的二硫化物对吲哚的电化学磺酰化

  摘要：

  A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions. (C) 2018 The Electrochemical Society.

  DOI：

  10.1149/2.0071807jes

文献信息

• Iron(III) Chloride: A Versatile Catalyst for the Practical Synthesis of 3-Sulfenylindoles
  作者：Jhillu Yadav、Basi Reddy、Yerabolu Reddy、Karanam Praneeth

  DOI：10.1055/s-0028-1088035

  日期：——

  The direct sulfenylation of indoles with aromatic thiols has been accomplished in the presence of 20 mol% of FeCl3 in refluxing acetonitrile to produce 3-arylthioindoles in relatively good to excellent yields and with high selectivity. This method works even with 2-unsubstituted indoles. thiolation - indoles - thiols - 3-arylthioindoles

  在芳族硫醇的存在下，在回流的乙腈中存在20 mol％的FeCl 3时，吲哚直接被亚磺酰基化，从而以相对较高的产率，优异的选择性和较高的选择性生产3-芳基硫代吲哚。该方法甚至适用于2-未取代的吲哚。 硫醇化-吲哚-硫醇-3-芳基硫代吲哚
• [EN] BINDING FUNCTION3 (BF3) SITE COMPOUNDS AS THERAPEUTICS AND METHODS FOR THEIR USE<br/>[FR] COMPOSÉS DE SITE DE (BF3) AYANT UNE FONCTION 3 DE LIAISON UTILISÉS EN TANT QU'AGENTS THÉRAPEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2015154169A1

  公开（公告）日：2015-10-15

  This invention provides compound having a structure of Formulas: Uses of such compounds for treatment of various indications, including prostate cancer as well as methods of treatment involving such compounds are also provide.

  这项发明提供了具有以下结构的化合物：这些化合物的用途包括治疗各种症状，包括前列腺癌，还提供了涉及这些化合物的治疗方法。
• A tetra-n-butylammonium iodide mediated reaction of indoles with Bunte salts: efficient 3-sulfenylation of indoles under metal-free and oxidant-free conditions
  作者：Jian Li、Zhong-Jian Cai、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c6ob01528j

  日期：——

  A highly efficient tetra-n-butylammonium iodide (TBAI) triggered procedure for 3-sulfenylation of indoles with Bunte salts is demonstrated. This protocol provides a simple strategy to prepare 3-alkylthioindoles and 3-arylthioindoles from the corresponding indoles under metal-free and oxidant-free conditions.

  证明了一种高效的四正丁基碘化铵（TBAI）引发的用布恩特盐将吲哚进行3-磺酰化的方法。该方案提供了一种简单的策略，可以在无金属和无氧化剂的条件下，由相应的吲哚制备3-烷基硫代吲哚和3-芳基硫代吲哚。
• Binding function 3 (BF3) site compounds as therapeutics and methods for their use
  申请人：THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：US10351527B2

  公开（公告）日：2019-07-16

  This invention provides compound having a structure of Formulas: Uses of such compounds for treatment of various indications, including prostate cancer as well as methods of treatment involving such compounds are also provide.

  本发明提供了具有式结构的化合物：本发明还提供了此类化合物在治疗包括前列腺癌在内的各种适应症方面的用途，以及涉及此类化合物的治疗方法。
• Binding Function 3 (BF3) site compounds as therapeutics and methods for their use
  申请人：THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：US10633338B2

  公开（公告）日：2020-04-28

  This invention provides compound having a structure of Formulas: Uses of such compounds for treatment of various indications, including prostate cancer as well as methods of treatment involving such compounds are also provide.

  本发明提供了具有以下结构式的化合物： 本发明还提供了此类化合物在治疗包括前列腺癌在内的各种适应症方面的用途，以及涉及此类化合物的治疗方法。