3-styrenylindole | 24620-45-9

• 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: 3-styrenylindole
• 英文别名: 3-styrylindole；ZINC01037115；3-<1-Phenyl-vinyl>-indol；3-(2-Phenylvinyl)-indol；3-styryl-1H-indole；3-(2-phenylethenyl)-1H-indole
• CAS: 24620-45-9
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: DZMBGFYPZAPYOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-styrenylindole 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以75%的产率得到3-(3-indolyl)-2-phenyl-1-benzyl-1,2,3,4-tetrahydrocyclopent[b]indole
  参考文献：
  名称：

  Exploring stereoselectivity of 3-indolyl cyclopent[b]indoles: A parallel synthesis and anti-EGFR study on human cancer cells

  摘要：

  We synthesized a series of novel 3-indolyl cyclopent[b]indoles by trifluoroacetic acid mediated cyclodimerizations. The reaction showed high stereoselectivity and moderate to good yields. The influencing factors for stereoselectivity were systematically analyzed and a stepwise reaction mechanism was proposed. The cell viability tests in two colon and two lung cancer cell lines indicated the 1-benzyl-2phenyl-group in 3-indolyl cyclopent[b]indoles was critical for the observed lower IC(50)s in these compounds. Western blot analysis demonstrated that the compound inhibited the expression and phosphorylation of EGFR through altered HSP90 expression. Further cell cycle and cell cycle check point protein analyses showed expected anti-cellular proliferation and cell cycle arresting properties associated with suppressed EGFR expression and phosphorylation. These data revealed a novel molecular mechanism explaining the observed cytotoxicities for these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.012
• 作为产物：
  描述：

  3-吲哚甲醛 、 苄基三苯基氯化膦 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以3.05 g的产率得到3-styrenylindole
  参考文献：
  名称：

  一种高产酸的磺酰亚胺类光产酸剂

  摘要：

  本发明公开一种高产酸的磺酰亚胺类光产酸剂，具有通式(A)所示结构。该产酸剂对波长300‑450nm特别是365nm(I线)和405nm(H线)的活性能量射线具有高灵敏度，溶解性好且产酸性强的光产酸剂。

  公开号：

  CN112552280A

文献信息

• MOFs Extend the Lifetime of Pd(II) Catalyst for Room Temperature Alkenylation of Enamine-Like Arenes
  作者：Francisco G. Cirujano、Pedro Leo、Jannick Vercammen、Simon Smolders、Gisela Orcajo、Dirk E. De Vos

  DOI：10.1002/adsc.201800817

  日期：2018.10.18

  The synthesis of pharmaceutically relevant scaffolds, such as substituted indoles or uracils, through the alkenylation of the “enamine‐like” aromatic C−H bond is performed at room temperature using catalytic amounts of Pd(OAc)2 in the presence of redox active, stable and reusable metal‐organic microporous frameworks. This is the first time that redox/acid active sites in the porous, non‐toxic and earth

  在室温下，在氧化还原活性物质存在的情况下，使用催化量的Pd（OAc）2，通过“类烯胺”芳族CH键的烯基化反应合成药物相关的支架，例如取代的吲哚或尿嘧啶。稳定且可重复使用的金属有机微孔框架。这是首次在多孔，无毒且富含泥土的坚固MOF-74平台上使用氧化还原/酸活性位点，以避免在环境条件下工作的阳离子Pd物种快速失活。
• Enantioselective Domino Reaction of 3-Vinylindole and <i>p</i>-Quinone Methides Enabled by Chiral Imidodiphosphoric Acids: Asymmetric Synthesis of Multisubstituted 3-Indolyl Cyclopenta[<i>b</i>]indoles
  作者：Ji-Gang Gao、Xu-Kai Guan、Dong-Yang Sun、Heng Zhang、Wen-Hua Mi、Xiang-Shuo Qin、Guang-Liang Zhang、Suoqin Zhang

  DOI：10.1021/acs.orglett.1c01600

  日期：2021.6.18

  development of a stereoselective method for the rapid assembly of structurally complex molecules remains fascinating and challenging in synthetic organic chemistry. Here, we report an enantioselective domino reaction between 3-vinylindole and p-quinone methide for the preparation of 3-indolyl cyclopenta[b]indoles containing multiple chiral centers. Chiral imidodiphosphoric acids enable this cascade asymmetric

  用于快速组装结构复杂分子的立体选择性方法的开发在合成有机化学中仍然具有吸引力和挑战性。在这里，我们报告了 3-乙烯基吲哚和对-醌甲基化物之间的对映选择性多米诺反应，用于制备含有多个手性中心的 3-吲哚基环戊 [ b ] 吲哚。手性亚胺二磷酸实现了这种级联不对称过程，提供了一系列具有优异收率 (≤99%)、对映选择性 (≤99%) 和非对映选择性 (≤20:1 dr) 的产品。
• Diastereo- and Enantioselective Construction of Dihydrobenzo[<i>e</i>]indole Scaffolds via Catalytic Asymmetric [3 + 2] Cycloannulations
  作者：Can Li、Dan-Ni Xu、Chun Ma、Guang-Jian Mei、Feng Shi

  DOI：10.1021/acs.joc.8b01217

  日期：2018.8.17

  The first catalytic asymmetric construction of chiral dihydrobenzo[e]indole scaffolds has been established in a highly diastereo- and enantioselective mode (30 examples, up to 99% yield, >95:5 dr, >99% ee), which makes use of chiral phosphoric acid-catalyzed [3 + 2] cycloannulations of azonaphthalene derivatives with 3-vinylindoles. This reaction also represents the first catalytic asymmetric cycloannulation

  手性二氢苯并[ e ]吲哚骨架的第一个催化不对称结构已经建立在高度非对映和对映选择性的模式下（30个实例，产率高达99％，> 95：5 dr，> 99％ee），它利用了手性磷酸与3-乙烯基吲哚的偶氮萘衍生物的[3 + 2]环环化反应。该反应也代表了氮杂萘衍生物与烯烃的首次催化不对称环环化，这不仅为构建对映体富集的二氢苯并[ e ]吲哚骨架提供了有用的方法，而且还促进了氮杂萘衍生物催化不对称反应的化学反应。
• Enantioselective gold-catalyzed intermolecular [2+2] <i>versus</i> [4+2]-cycloadditions of 3-styrylindoles with <i>N</i>-allenamides: observation of interesting substituent effects
  作者：Yidong Wang、Peichao Zhang、Yuan Liu、Fei Xia、Junliang Zhang

  DOI：10.1039/c5sc01827g

  日期：——

  The cycloaddition mode ([2+2] vs. [4+2]) can be unexpectedly switched by the simple modification of the N-substituent of the 3-styrylindoles.

  环加成模式（[2+2] vs. [4+2]）可以通过对3-苯乙烯基吲哚的N-取代基进行简单修改而意外地切换。
• Pd(II) supramolecular cage-catalyzed successive oxidative coupling: One-pot and regioselective synthesis of functionalized carbazoles from indoles
  作者：Xi-Ren Wu、He-Long Peng、Lian-Qiang Wei、Li-Ping Li、Su-Yang Yao、Bao-Hui Ye

  DOI：10.1016/j.catcom.2019.02.023

  日期：2019.5

  compound in pharmaceuticals and functional materials. A new Pd(II) supramolecular cage-catalyzed protocol for the synthesis of multifunctional carbazoles from indoles is described through regioselective successive oxidative Heck reactions. This new protocol is highly efficient, with a low Pd (2.4 mol%) catalyst loading and good compatibility for both N-H free and N-protected indole substrates. Moreover, it

  咔唑是药物和功能材料中的重要化合物。通过区域选择性连续氧化Heck反应描述了一种新的Pd（II）超分子笼催化的方案，用于从吲哚合成多功能咔唑。该新方案非常高效，具有低Pd（2.4 mol％）的催化剂负载量，并且对无NH和受N保护的吲哚底物都具有良好的相容性。而且，它可以通过一锅两步法用于合成具有各种官能团的咔唑。优异的催化活性可以归因于超分子笼状结构在笼状表面上均匀分布和定义明确的Pd（II）活性中心中的独特特性。