2-(1-allyl-1H-indol-3-yl)-N-methylethan-1-amine | 1344042-89-2

• 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: 2-(1-allyl-1H-indol-3-yl)-N-methylethan-1-amine
• 英文别名: N1-allyl-N10-methyltryptamine；N-methyl-2-(1-prop-2-enylindol-3-yl)ethanamine
• CAS: 1344042-89-2
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: NLUJMYYJDGCCCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  17
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(1-allyl-1H-indol-3-yl)-N-methylethan-1-amine 在 盐酸 、 4-二甲氨基吡啶 、 溶剂黄146 、 二甲基亚砜 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 N-(2-(1-allyl-2-oxoindolin-3-yl)ethyl)-N-methyl-3-oxo-3-phenylpropanamide
  参考文献：
  名称：

  次碘酸胍催化羟吲哚与β-二羰基的分子内氧化偶联反应

  摘要：

  螺[二氢吲哚-3,4'-哌啶]是存在于各种生物活性化合物中的基本基序。在这里，我们报道了在次碘酸胍催化剂存在下，羟吲哚与β-二羰基的分子内氧化偶联反应，以中等至优异的产率提供螺偶联产物。此外，源自手性胍有机催化剂的手性次碘酸盐催化剂对于具有挑战性的不对称碳-碳键形成反应是有效的，提供光学活性的螺[indoline-3,4'-哌啶]。

  DOI：

  10.1021/acs.joc.2c02500
• 作为产物：
  描述：

  N1-allyl-N10-methyl-N10-Boc-tryptamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到2-(1-allyl-1H-indol-3-yl)-N-methylethan-1-amine
  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

文献信息

• Synthesis and evaluation of N1-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands
  作者：Edwin G. Pérez、Bruce K. Cassels、Christoph Eibl、Daniela Gündisch

  DOI：10.1016/j.bmc.2012.04.050

  日期：2012.6

  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.
• Guanidinium Hypoiodite-Catalyzed Intramolecular Oxidative Coupling Reaction of Oxindoles with β-Dicarbonyls
  作者：Kota Sugimoto、Io Mori、Takanari Kato、Koji Yasui、Ban Xu、Choon Hong Tan、Minami Odagi、Kazuo Nagasawa

  DOI：10.1021/acs.joc.2c02500

  日期：——

  Spiro[indoline-3,4′-piperidine] is a fundamental motif present in various biologically active compounds. Here, we report an intramolecular oxidative coupling reaction of oxindoles with β-dicarbonyls in the presence of a guanidinium hypoiodite catalyst, providing spiro-coupling products in moderate to excellent yields. Furthermore, a chiral hypoiodite catalyst derived from the chiral guanidinium organocatalyst

  螺[二氢吲哚-3,4'-哌啶]是存在于各种生物活性化合物中的基本基序。在这里，我们报道了在次碘酸胍催化剂存在下，羟吲哚与β-二羰基的分子内氧化偶联反应，以中等至优异的产率提供螺偶联产物。此外，源自手性胍有机催化剂的手性次碘酸盐催化剂对于具有挑战性的不对称碳-碳键形成反应是有效的，提供光学活性的螺[indoline-3,4'-哌啶]。