3,3'-二吲哚基二硫醚 | 61830-39-5

• 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: 3,3'-二吲哚基二硫醚
• 英文名称: 3,3'-Diindolyl-disulfid
• 英文别名: 3,3'-Indolyl-disulfid；3,3'-Diindolyl Disulphide；3-(1H-indol-3-yldisulfanyl)-1H-indole
• CAS: 61830-39-5
• 化学式: C₁₆H₁₂N₂S₂
• 分子量: 296.417
• InChiKey: NNBHHSOOWJVMMD-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220°C dec.
• 溶解度：
  二甲基亚砜（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3'-二吲哚基二硫醚 在 氢氧化钾 、 四丁基硫酸氢铵 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.75h， 生成 2,3'-bis(indolyl) sulfide
  参考文献：
  名称：

  3-（芳硫基）吲哚的新途径：在海洋生物碱 Echinosulfone A 的 3,3'-双（吲哚基）砜核心合成中的应用

  摘要：

  基于芳基格氏试剂或锂化杂芳烃与苯磺酰基保护的 3,3'-b ...

  DOI：

  10.1055/s-2006-950427
• 作为产物：
  描述：

  (1H-吲哚-3-基磺酰基)盐酸乙脒碘化氢 在 sodium hydroxide 作用下， 反应 0.5h， 生成 3,3'-二吲哚基二硫醚
  参考文献：
  名称：

  Nagarajan, K.; Arya, V. P.; Parthasarathy, T. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 8, p. 672 - 679

  摘要：

  DOI：

文献信息

• Catalyst-Triggered Highly Selective C−S and C−Se Bond Formation by C−H Activation
  作者：Yong Yang、Wanmei Li、Beibei Ying、Hanxiao Liao、Chao Shen、Pengfei Zhang

  DOI：10.1002/cctc.201600589

  日期：2016.9.21

  Nickel or iron salts catalyzing the selective synthesis of 3,3‐indolyl disulfide (diselenide) and 3,3‐indolyl thioether (selenide) directly from indole through C−H activation are reported. The effect of iodine element was beneficial in the novel metal‐catalyzed circulation system. A wide variety of functional groups could be tolerated under the reaction conditions.

  据报道，镍或铁盐可通过CH活化直接从吲哚催化3,3-吲哚基二硫化物（二硒化物）和3,3-吲哚基硫醚（硒化物）的选择性合成。在新型的金属催化循环系统中，碘元素的作用是有益的。在反应条件下可以容许多种官能团。
• Synthesis of 3-(Arylthio)indoles and Related Compounds by Reactions of Metalated Aromatics or Heterocycles with Protected 3,3′-Dithiobisindoles
  作者：Tomasz Janosik、Hamid Shirani

  DOI：10.1055/s-2007-983818

  日期：2007.9

  An efficient and practical strategy for the synthesis of new 3-(arylthio)indoles and related compounds has been developed, involving cleavage of readily available protected 3,3′-dithiobisindoles with metalated aromatics or heterocycles.

  已经开发了一种用于合成新的 3-(芳硫基)吲哚和相关化合物的有效且实用的策略，包括用金属化芳烃或杂环化合物裂解容易获得的受保护的 3,3'-二硫代双吲哚。
• Tetrathiaporphyrine: A Novel Natural Product from <i>Allium</i> Subgenus <i>Melanocrommyum</i>
  作者：Fabian Rüger、Andreas Heine、Doru Vornicescu、Michael Keusgen

  DOI：10.1002/ejoc.202201481

  日期：2023.5.22

  A novel purple‐red pigment from the plant genus of Allium (onions, leeks), subgenus Melanocrommyum (drumstick onions), is described. Because of this pigment, which reminds of blood, some species of the subgenus Melanocrommyum are used in Southwest and Central Asia as herbal medications, as spices or as vegetables. A proposal for the formation of this structure is provided, which is the first example of a tetrathiaporphyrin in nature. The described substance shows low stability towards thermal stress, light and oxidant; additionally, its symmetric nature made structural elucidation a challenge. It could be shown that, contrary to previous reports, the structure of the red pigment is that of a tetrathiaporphyrin. Full structure elucidation was only possible by X‐ray crystallography and total synthesis of the intended molecule. Further on, the newly discovered red pigment was used for the modification of nanoparticles and monitoring its polymerization events using SPR.

  摘要 描述了一种来自葱属（洋葱、韭菜）植物 Melanocrommyum 亚属（鼓槌洋葱）的新型紫红色色素。由于这种色素让人联想到血液，Melanocrommyum 亚属的一些物种在西南亚和中亚被用作草药、香料或蔬菜。本文提出了这种结构的形成原因，这是自然界中首个四硫代卟啉的实例。所描述的物质对热应力、光和氧化剂的稳定性较低；此外，它的对称性也给结构阐释带来了挑战。结果表明，与之前的报道相反，这种红色素的结构是一种四硫代卟啉。只有通过 X 射线晶体学和对目标分子的全合成，才能完全阐明其结构。此外，新发现的红色素还被用于纳米颗粒的改性，并利用 SPR 技术监测其聚合反应。
• A Route to α-Fluoroalkyl Sulfides from α-Fluorodiaroylmethanes
  作者：Ya-mei Lin、Wen-bin Yi、Wan-zhao Shen、Guo-ping Lu

  DOI：10.1021/acs.orglett.5b03654

  日期：2016.2.5

  alpha,alpha-Difluorodiaroylmethane can be used as a nucleophilic difluoromethylation reagent for generating alpha-thioaryl-alpha,alpha-difluoroacetophenones ((ArCOCF2SAr)-C-1) and difluoromethylthiolated arenes (ArSCF2H) under transition-metal-free conditions. The reaction selectivity is mainly dependent on temperature. The method has also been extended to the synthesis of alpha-thioaryl-alpha-monofluoroacetophenones using alpha-monofluorodibenzoylmethane. Moreover, the benzoyl cation derived from alpha,alpha-difluorodibenzoylmethane can react with nucleophiles to afford the desired products in a one-pot process.
• Gurevich, P. A.; Razumov, A. I.; Komina, T. V., Journal of general chemistry of the USSR, 1985, vol. 55, # 6, p. 1187 - 1190
  作者：Gurevich, P. A.、Razumov, A. I.、Komina, T. V.、Klimentova, G. Yu.、Zykova, T. V.

  DOI：——

  日期：——