1-decyl-1H-indole | 163806-31-3

• 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: 1-decyl-1H-indole
• 英文别名: N-n-decylindole；N-decylindole；1H-Indole, 1-decyl-；1-decylindole
• CAS: 163806-31-3
• 化学式: C₁₈H₂₇N
• 分子量: 257.419
• InChiKey: RAOWSRKEACYRLX-UHFFFAOYSA-N

物化性质

• 沸点：
  378.6±11.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-decyl-1H-indole 在 溶剂黄146 作用下， 以 水 、 丙酮 为溶剂， 反应 40.0h， 生成 (1-decyl-1H-indol-3-yl)-N,N,N-trimethylmethanaminium iodide
  参考文献：
  名称：

  Synthesis and evaluation of N1-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands

  摘要：

  In this study thirty-three novel indole derivatives were designed and synthesized based on the structure of deformylflustrabromine B (1), a metabolite isolated from the marine bryozoan Flustra foliacea L. The syntheses were carried out using standard methodologies and in good yields. The molecules were tested for their affinities for the alpha 4 beta 2*, alpha 3 beta 4*, alpha 7* and (alpha 1)(2)beta 1 gamma delta nicotinic acetylcholine receptor (nAChR) sub-types. Binding assays showed that, among these ligands, compound 7c exhibited the highest affinity with K-i = 136.1, 93.9 and 862.4 nM for the alpha 4 beta 2*, alpha 3 beta 4*, and alpha 7* nAChRs subtypes, respectively. These results indicated that the indole core might be a useful scaffold for the development of new potent and selective nAChR ligands. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.050
• 作为产物：
  描述：

  癸醇 在 Pt-loaded HBEA 作用下， 以 邻二甲苯 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 66.0h， 生成 1-decyl-1H-indole
  参考文献：
  名称：

  使用Pt / HBEA催化剂将伯醇与吲哚选择性地进行N-烷基化

  摘要：

  负载铂的HBEA（H +交换的BEA沸石）被发现是一种有效且可重复使用的非均相催化剂，用于在借用氢方法的驱动下在无添加剂的条件下用脂肪族和苄基伯醇对吲哚进行区域选择性N-烷基化。结构和机理研究表明，Pt金属簇上的Pt 0位点和沸石的Brønsted酸位点是一种协同机制，其中Pt 0位点负责脱氢/氢化步骤，而Brønsted酸位点负责区域选择性缩合将带有醛的吲哚制成烯胺中间体。

  DOI：

  10.1039/c4gc01419g

文献信息

• Selective and Efficient Formylation of Indoles (C3) and Pyrroles (C2) Using 2,4,6-Trichloro-1,3,5-Triazine/Dimethylformamide (TCT/DMF) Mixed Reagent
  作者：Nasser Iranpoor、Farhad Panahi、Soodabeh Erfan、Fatemeh Roozbin

  DOI：10.1002/jhet.2652

  日期：2017.3

  one equivalent of 2,4,6‐trichloro‐1,3,5‐triazine (cyanuric chloride) generates an easy handling formylating agent for the efficient formylation of these classes of compounds to give the corresponding aldehydes under mild reaction conditions. This procedure was highly efficient, and a range of formylated indoles and pyrroles were obtained in good to excellent yields.

  这项研究介绍了一种有效的方法，分别在C（3）和C（2）的位置对吲哚和吡咯进行选择性甲酰化。三当量的N，N-二甲基甲酰胺和一当量的2,4,6-三氯-1,3,5-三嗪（氰尿酰氯）的混合物可生成易于处理的甲酰化剂，以有效地将此类化合物甲酰化为在温和的反应条件下得到相应的醛。该方法是高效的，并且以良好至优异的产率获得了一系列甲酰化的吲哚和吡咯。
• An Efficient Ultrasound-Assisted Synthesis of<i>N</i>-Alkyl Derivatives of Carbazole, Indole, and Phenothiazine
  作者：Sanhu Zhao、Jin Kang、Yuting Du、Jingyan Kang、Xiaoni Zhao、Yinfeng Xu、Ruixi Chen、Qianqian Wang、Xitao Shi

  DOI：10.1002/jhet.1652

  日期：2014.5

  Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N‐DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs

  咔唑，吲哚和吩噻嗪等带有氮原子的酸性氢原子杂环化合物可以在氢氧化钾为碱的情况下，在DMSO或N，N -DMF中有效地烷基化。在几乎所有情况下，都会大大缩短反应时间，并明显提高产率，同时提高产品质量。
• An approach to functionalized carbazoles from <i>Z</i>-enoate propargylic alcohols. A unified total synthesis of <i>N</i>-Me-carazostatin, <i>N</i>-Me-carbazoquinocin C and <i>N</i>-Me-lipocarbazole A4
  作者：Debayan Roy、Prabhakararao Tharra、Beeraiah Baire

  DOI：10.1039/d2cc03526j

  日期：——

  of an acid catalyzed, intramolecular benzannulation of indoles for the synthesis of functionalized carbazoles has been reported. The indole appended Z-enoate propargylic alcohols have been employed. The N-EDG-indoles involve the 5-exo-dig cyclization followed by 1,2-migration to give the carbazole-butenoates, whereas the N-EWG-indoles undergo the Z-enoate assisted Meyer–Schuster rearrangement to give

  据报道，开发了一种酸催化的吲哚分子内苯并环化，用于合成官能化咔唑。已使用吲哚附加的Z-烯酸炔丙醇。N -EDG-吲哚涉及 5 - exo-dig环化，然后是 1,2-迁移以产生咔唑-丁烯酸酯，而N -EWG-吲哚经历Z-烯酸酯辅助的 Meyer-Schuster 重排以产生二氢咔唑- 4-氧代丁酸。利用 2-甲基-咔唑-丁醛（从相应的咔唑-丁酸酯中获得）作为关键中间体，我们开发了一种有效合成N-Me-carazostatin、N -Me-carbazoquinocin C 和N -Me-lipocar​​bazole A4。
• Efficient thiocyanation of aromatic compounds using NH4SCN, DMSO and H2SO4
  作者：Mohammad Abbasi、Najmeh Nowrouzi、Hamed Sedaghat

  DOI：10.1016/j.tetlet.2022.153929

  日期：2022.7

  A simple, efficient, and smooth thiocyanation of indoles, phenols and aniline derivatives using NH4SCN, DMSO and H2SO4 in DMF is introduced. Using this procedure, diverse indoles and N-alkyl indoles are selectively thiocyanated at the C-3 position. para-free anilines, N-alkyl anilines and phenols undergo thiocyanation at the para position selectively.

  介绍了在 DMF 中使用 NH 4 SCN、DMSO 和 H 2 SO 4对吲哚、苯酚和苯胺衍生物进行简单、高效、平稳的硫氰化反应。使用该程序，多种吲哚和N-烷基吲哚在 C-3 位被选择性硫氰化。无对位苯胺、N-烷基苯胺和苯酚在对位选择性地进行硫氰化。
• Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using N-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents
  作者：Xiao Yun Chen、Yaonan Tang、Xinran Xiang、Yisong Tang、Mingyang Huang、Shaojun Zheng、Cuifeng Yang

  DOI：10.3390/molecules28083380

  日期：——

  A green one-pot 2,3,6-trifunctionalization of N-alkyl/aryl indoles was achieved by adding three equivalents of N-Br sulfoximine to the indole solution. A variety of 2-sulfoximidoyl-3,6-dibromo indoles were prepared with 38–94% yields using N-Br sulfoximines as both brominating and sulfoximinating reagents. Based on the results of controlled experiments, we propose that a radical substitution involving 3,6-dibromination and 2-sulfoximination occurs in the reaction process. This is first time that 2,3,6-trifunctionalization of indole in one pot has been achieved.

  通过在吲哚溶液中加入三当量的 N-Br 亚磺酰亚胺，实现了 N-烷基/芳基吲哚的 2,3,6-三官能团化。使用 N-Br 亚磺酰亚胺作为溴化和亚磺酰亚胺化试剂，制备了多种 2-亚磺酰亚胺基-3,6-二溴吲哚，收率为 38-94%。根据对照实验的结果，我们认为在反应过程中发生了涉及 3,6-二溴和 2-亚磺酰亚胺的自由基取代反应。这是首次在一锅中实现吲哚的 2,3,6-三官能化。