1-(1H-indol-2-yl)-3-(4-methoxyphenyl)prop-2-yn-1-one | 1413923-09-7

• 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-(1H-indol-2-yl)-3-(4-methoxyphenyl)prop-2-yn-1-one
• CAS: 1413923-09-7
• 化学式: C₁₈H₁₃NO₂
• 分子量: 275.307
• InChiKey: VXPCERYRVQVDLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 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：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1H-indol-2-yl)-3-(4-methoxyphenyl)prop-2-yn-1-one 在 三氟甲磺酸 、 caesium carbonate 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 (Z)-(1,2-diphenyl-3H-cyclopenta[b]quinolin-3-ylidene)(4-methoxyphenyl)methanol
  参考文献：
  名称：

  Brønsted-Acid-Promoted C2–N1选择性C2-N1环膨胀吲哚对环戊二烯[b]喹啉的反应

  摘要：

  已经开发了一种新的布朗斯台德酸促进的吲哚选择性 C2-N1 扩环反应，为稠合喹啉的制备提供了一种快速有效的方案。以高产率获得了多种相应的喹啉。对照实验表明，C2-螺二氢吲哚可能是这种 C2-N1 扩环反应的中间体。该工艺的显着优势包括出色的产率、良好的官能团耐受性和操作简单。

  DOI：

  10.1021/acs.orglett.1c04332
• 作为产物：
  描述：

  吲哚-2-羧酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(1H-indol-2-yl)-3-(4-methoxyphenyl)prop-2-yn-1-one
  参考文献：
  名称：

  Synthesis and evaluation of indole-containing 3,5-diarylisoxazoles as potential pro-apoptotic antitumour agents

  摘要：

  A series of novel indole-containing diarylisoxazoles has been synthesised, based on our previous work on the synthesis and pro-apoptotic antitumour activity of indole-based diaryl 1,2,4-oxadiazoles. Concise synthetic routes to both 3-(indol-2-yl)-5-phenylisoxazoles and 5-(indol-2-yl)-3-phenylisoxazoles have been developed with full regiochemical control, bearing substituents on the indole ring, indole nitrogen, and/or phenyl group. Additionally a series of the related 5-(1H-indol-5-yl)-3-phenylisoxazoles has been prepared. In vitro evaluation in human cancer cell lines Colo320 (colon) and Calu-3 (lung) revealed preferential antiproliferative activity within the 5-(indol-5-yl)-3-phenylisoxazole series (low micromolar IC50). Further analysis revealed the ability of the indol-5-yl series to induce expression of effector caspases-3 and -7, and retention of viability of the human bronchial smooth muscle cell (BSMC) control cell population (particularly for compounds 18c and 18e). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.009

文献信息

• Selective Synthesis of Pyrano[3,2-<i>b</i>]indoles or Cyclopenta[<i>b</i>]indoles Tethered with Medium-Sized Rings via Cascade C–C σ-Bond Cleavage and C–H Functionalization
  作者：Mengdan Wang、Yajie Yang、Liqiang Yin、Ye Feng、Yanzhong Li

  DOI：10.1021/acs.joc.0c02310

  日期：2021.1.1

  atom-economical tandem reactions have been developed for the synthesis of pyrano[3,2-b]indoles or cyclopenta[b]indoles tethered with 7-, 8-, or 9-membered rings. These reactions first undergo a carbon–carbon σ-bond cleavage reaction of cyclic β-ketoesters. Next, in the presence of CuCl2 and Ag2CO3, intramolecular O–H/C–H coupling occurs to give pyrano[3,2-b]indoles. This is the first example for capture of the enoloxyl

  已经开发出高度原子经济的串联反应，用于合成与7、8或9元环连接的吡喃并[3,2- b ]吲哚或环戊[ b ]吲哚。这些反应首先经历环状β-酮酸酯的碳-碳σ键裂解反应。接下来，在CuCl 2和Ag 2 CO 3的存在下，发生分子内O–H / C–H偶联，生成吡喃并[3,2- b ]吲哚。这是捕获分子内C–O键形成反应的烯氧基自由基的第一个例子，而C3亲核加成反应使用TsOH·H 2 O提供了环戊[ b ]吲哚。
• Synthesis and evaluation of indole-containing 3,5-diarylisoxazoles as potential pro-apoptotic antitumour agents
  作者：Siti Farah Md Tohid、Noha I. Ziedan、Fabio Stefanelli、Stefano Fogli、Andrew D. Westwell

  DOI：10.1016/j.ejmech.2012.08.009

  日期：2012.10

  A series of novel indole-containing diarylisoxazoles has been synthesised, based on our previous work on the synthesis and pro-apoptotic antitumour activity of indole-based diaryl 1,2,4-oxadiazoles. Concise synthetic routes to both 3-(indol-2-yl)-5-phenylisoxazoles and 5-(indol-2-yl)-3-phenylisoxazoles have been developed with full regiochemical control, bearing substituents on the indole ring, indole nitrogen, and/or phenyl group. Additionally a series of the related 5-(1H-indol-5-yl)-3-phenylisoxazoles has been prepared. In vitro evaluation in human cancer cell lines Colo320 (colon) and Calu-3 (lung) revealed preferential antiproliferative activity within the 5-(indol-5-yl)-3-phenylisoxazole series (low micromolar IC50). Further analysis revealed the ability of the indol-5-yl series to induce expression of effector caspases-3 and -7, and retention of viability of the human bronchial smooth muscle cell (BSMC) control cell population (particularly for compounds 18c and 18e). (C) 2012 Elsevier Masson SAS. All rights reserved.
• Brønsted-Acid-Promoted Selective C2–N1 Ring-Expansion Reaction of Indoles toward Cyclopenta[<i>b</i>]quinolines
  作者：Yajie Yang、Yilin Zhu、Liqiang Yin、Lu Cheng、Chengyu Wang、Yanzhong Li

  DOI：10.1021/acs.orglett.1c04332

  日期：2022.1.28

  A novel Brønsted-acid-promoted selective C2–N1 ring-expansion reaction of indoles has been developed that provides a rapid and efficient protocol for the preparation of fused quinolines. A variety of corresponding quinolines were obtained in high yields. Controlled experiments revealed that C2-spiroindolenines might be intermediates of this C2–N1 ring-expansion reaction. The notable advantages of this

  已经开发了一种新的布朗斯台德酸促进的吲哚选择性 C2-N1 扩环反应，为稠合喹啉的制备提供了一种快速有效的方案。以高产率获得了多种相应的喹啉。对照实验表明，C2-螺二氢吲哚可能是这种 C2-N1 扩环反应的中间体。该工艺的显着优势包括出色的产率、良好的官能团耐受性和操作简单。