1-(3-phenylprop-2-yn-1-yl)-1H-indole-2-carbaldehyde | 600727-40-0

• 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-(3-phenylprop-2-yn-1-yl)-1H-indole-2-carbaldehyde
• 英文别名: 1-(3-phenylprop-2-ynyl)-1H-indole-2-carbaldehyde；1-(3-Phenylprop-2-ynyl)indole-2-carbaldehyde
• CAS: 600727-40-0
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: FMRKOEANWFNLNY-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  464.2±25.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-phenylprop-2-yn-1-yl)-1H-indole-2-carbaldehyde 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以61%的产率得到3-bromo-1-(3-phenylprop-2-yn-1-yl)-1H-indole-2-carbaldehyde
  参考文献：
  名称：

  Gold-Catalyzed Domino Cycloisomerization/Alkoxylation: An Entry to 3,4-Dihydro-1H-[1,4]oxazino[4,3-a]indole

  摘要：

  DOI：

  10.1021/acs.joc.1c02030
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 在 copper(l) iodide 、 palladium diacetate 、 sodium hydride 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-dimethyl-d₆-formamide 为溶剂， 反应 9.5h， 生成 1-(3-phenylprop-2-yn-1-yl)-1H-indole-2-carbaldehyde
  参考文献：
  名称：

  N-炔丙基化的吡咯和吲哚-甲醛与氨，烷基胺和支链胺反应的机理研究：合成和理论研究

  摘要：

  TOC文本：研究了N-炔丙基化吡咯和吲哚甲醛与不同类型胺的反应。产品的性质取决于所用胺的类型。与烷基胺的反应形成了相应的吡嗪酮衍生物，而支链胺导致了吲哚嗪衍生物的形成。通过计算方法研究了反应机理。

  DOI：

  10.1002/ejoc.201900084

文献信息

• Gold-Catalyzed Oxime–Oxime Rearrangement
  作者：Sinem Guven、Merve Sinem Ozer、Serdal Kaya、Nurettin Menges、Metin Balci

  DOI：10.1021/acs.orglett.5b01041

  日期：2015.6.5

  The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one

  研究了具有炔丙基连接到氮原子上的吡咯和吲哚肟的金催化反应。在金催化剂的存在下，对于末端炔烃观察到环化的选择性6 -endo-dig模式，引起吡嗪N-氧化物的形成。然而，与取代炔烃的反应通过7-内-挖-环化过程将肟官能团从一个碳原子分子内转移到另一个碳原子上。这种转变在文献中是空前的，被称为肟－肟重排。
• Silver-catalyzed synthesis of pyrrolopiperazine fused with oxazine/imidazole <i>via</i> a domino approach: evaluation of anti-cancer activity
  作者：K. Shiva Kumar、N. Praveen Kumar、Bandari Rajesham、Gugulothu Kishan、Sravani Akula、Rama Krishna Kancha

  DOI：10.1039/c7nj03608f

  日期：——

  domino synthesis of pyrrolopiperazine fused with oxazine/imidazole by the reaction of pyrrole-derived δ-alkynyl aldehydes and nucleophilic amines was performed. This domino strategy involves the formation of two new C–N bonds and one C–O/C–N bond, resulting in the formation of two new interesting fused heterocycles. Some of the synthesized compounds exhibit promising growth inhibitory activity against

  通过吡咯衍生的δ-炔醛与亲核胺的反应进行银催化的吡咯并哌嗪与恶嗪/咪唑融合的多米诺骨牌合成。这种多米诺骨牌策略涉及形成两个新的C–N键和一个C–O / C–N键，从而导致两个新的有趣的稠合杂环的形成。一些合成的化合物对白血病和乳腺癌细胞系显示出有希望的生长抑制活性。
• Copper catalyzed synthesis of fused benzimidazolopyrazine derivatives via tandem benzimidazole formation/annulation of δ-alkynyl aldehyde
  作者：Subburethinam Ramesh、Suman Kr Ghosh、Rajagopal Nagarajan

  DOI：10.1039/c3ob41044g

  日期：——

  A novel route to synthesize the biologically active benzimidazolopyrazine core is outlined. The reaction proceeds via tandem benzimidazole formation/annulations of indole, pyrrole and aliphatic δ-alkynyl aldehydes in the presence of copper salts and green solvents with moderate to good yields.

  概述了合成具有生物活性的苯并咪唑并吡嗪核心的新路线。在铜盐和绿色溶剂存在下，该反应通过吲哚、吡咯和脂肪族 δ-炔基醛的串联苯并咪唑形成/环化进行，产率中等至良好。
• Domino addition/annulation of δ-alkynylaldehydes and oxygen nucleophiles: a new entry to [1,4]oxazino[4,3-a]indoles
  作者：Giorgio Abbiati、Valentina Canevari、Solange Caimi、Elisabetta Rossi

  DOI：10.1016/j.tetlet.2005.08.102

  日期：2005.10

  The unusual [1,4]oxazino[4,3-a]indole nucleus was prepared, under mild reaction conditions, by reacting 1-alkynyl-1H-indole-2-carbaldehydes with various alkoxides, generated in situ from the corresponding alkyl, benzyl, allyl and propargyl alcohols. (c) 2005 Elsevier Ltd. All rights reserved.
• Intramolecular Cyclization of δ-Iminoacetylenes:  A New Entry to Pyrazino[1,2-<i>a</i>]indoles
  作者：Giorgio Abbiati、Antonio Arcadi、Alessandra Bellinazzi、Egle Beccalli、Elisabetta Rossi、Simona Zanzola

  DOI：10.1021/jo0502246

  日期：2005.5.1

  The synthesis of the pyrazino[1,2-alpha]indole nucleus was achieved by intramolecular cyclization of several 2-carbonyl-1-propargylindoles in the presence of ammonia. The reaction conditions were optimized using microwave heating and a pool of catalysts. Cyclization of 1-alkynylindole-2-carbaldehydes was easily accomplished under standard heating conditions, whereas microwave heating contributed to reduced reaction times and improved overall yields. Moreover, a fine-tuning of the microwave irradiation time made possible the selective synthesis of both pyrazino[1,2-alpha]indole isomers. TiCl4 proved the catalytic system of choice to achieve pyrazinoindoles in satisfactory yields starting from 1-alkynyl-2-acetylindoles and 1-alkynyl-2-benzoylindole derivatives. Also in these cases, microwave heating contributed to faster reactions and improved yields. The uncatalyzed versus catalyzed reaction mechanism is discussed.