1-(3-(4-methoxyphenyl)prop-2-yn-1-yl)-1H-indole-2-carbaldehyde | 853052-24-1

• 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-(4-methoxyphenyl)prop-2-yn-1-yl)-1H-indole-2-carbaldehyde
• 英文别名: 1-[3-(4-Methoxyphenyl)prop-2-ynyl]indole-2-carbaldehyde
• CAS: 853052-24-1
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: MKZXCDBJBZVIKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-(4-methoxyphenyl)prop-2-yn-1-yl)-1H-indole-2-carbaldehyde 在 氨 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以65%的产率得到3-(4-methoxy-benzyl)-pyrazino[1,2-a]indole
  参考文献：
  名称：

  Intramolecular Cyclization of δ-Iminoacetylenes:  A New Entry to Pyrazino[1,2-a]indoles

  摘要：

  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.

  DOI：

  10.1021/jo0502246
• 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-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1-(3-(4-methoxyphenyl)prop-2-yn-1-yl)-1H-indole-2-carbaldehyde
  参考文献：
  名称：

  黄金催化的肟-肟重排

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.5b01041

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。
• Gold-Catalyzed Divergent Ring-Closing Modes of Indole-Tethered Amino Allenynes
  作者：Benito Alcaide、Pedro Almendros、Israel Fernández、Fernando Herrera、Amparo Luna

  DOI：10.1002/chem.201705294

  日期：2018.1.26

  Indole‐tethered amino allenynes were chemodivergently cyclized for the controlled preparation of fused polycyclic indoles using gold catalysis. Double cyclization of terminal allenynes afforded hexacyclic 15 H‐indolo[1,2,3‐de]quinolino[3,2,1‐ij]quinoxalines, in which allenynes bearing a substituted alkyne at the terminal end generated 12,13‐dihydro‐7 H‐indolo[3,2‐c]acridines, which are 5‐membered cyclized

  使用金催化化学键合吲哚拴系的氨基艾伦炔，以化学方式控制稠合多环吲哚的制备。末端烯丙炔的双环化提供了六环15  H-吲哚[1,2,3- de ] quinolino [3,2,1- ij ]喹喔啉，其中末端带有取代炔烃的烯丙炔生成12,13-二氢- 7  H-吲哚并[3,2- c ] ac啶，为五元环化加合物。进行密度泛函理论计算以揭示反应性的这种差异。
• 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.
• Gold-Catalyzed Domino Cycloisomerization/Alkoxylation: An Entry to 3,4-Dihydro-1<i>H</i>-[1,4]oxazino[4,3-<i>a</i>]indole
  作者：Aurélien Dupeux、Véronique Michelet

  DOI：10.1021/acs.joc.1c02030

  日期：2021.12.17