1-methyl-5-vinyl-1H-indole | 85654-51-9

• 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: 1-methyl-5-vinyl-1H-indole
• 英文别名: 1-methyl-5-vinylindole；1H-Indole, 5-ethenyl-1-methyl-；5-ethenyl-1-methylindole
• CAS: 85654-51-9
• 化学式: C₁₁H₁₁N
• 分子量: 157.215
• InChiKey: GPHGDOPLVTVWBU-UHFFFAOYSA-N

物化性质

• 沸点：
  150-155 °C(Press: 7.5 Torr)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-methyl-5-vinyl-1H-indole 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 为溶剂， 反应 12.0h， 生成 (3-benzofuran-3-yl)-4-(5-cyclopropyl-1-methyl-1H-indol-3-yl)pyrrole-2,5-dione
  参考文献：
  名称：

  Structure-Based Design Leads to the Identification of Lithium Mimetics That Block Mania-like Effects in Rodents. Possible New GSK-3β Therapies for Bipolar Disorders

  摘要：

  More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3 beta (GSK-3 beta) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3 beta inhibitors. The best ligand in this series (having a K-i value of 4.6 nM against GSK-3 beta) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3 beta inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.

  DOI：

  10.1021/ja068969w
• 作为产物：
  描述：

  1-methyl-5-ethylindole 在 K-16 作用下， 以 苯 为溶剂， 生成 1-methyl-5-vinyl-1H-indole
  参考文献：
  名称：

  Zeiberlikh, F. N.; Starostenko, N. E.; Pavlova, L. V., Journal of Organic Chemistry USSR (English Translation), 1983, p. 388 - 392

  摘要：

  DOI：

文献信息

• Interrogating Pd(II) Anion Metathesis Using a Bifunctional Chemical Probe: A Transmetalation Switch
  作者：John J. Molloy、Ciaran P. Seath、Matthew J. West、Calum McLaughlin、Neal J. Fazakerley、Alan R. Kennedy、David J. Nelson、Allan J. B. Watson

  DOI：10.1021/jacs.7b11180

  日期：2018.1.10

  Ligand metathesis of Pd(II) complexes is mechanistically essential for cross-coupling. We present a study of halide→OH anion metathesis of (Ar)PdII complexes using vinylBPin as a bifunctional chemical probe with Pd(II)-dependent cross-coupling pathways. We identify the variables that profoundly impact this event and allow control to be leveraged. This then allows control of cross-coupling pathways

  Pd(II) 配合物的配体复分解对于交叉偶联在机械上是必不可少的。我们使用vinylBPin作为具有Pd（II）依赖性交叉偶联途径的双功能化学探针，对（Ar）PdII复合物的卤化物→OH阴离子复分解进行了研究。我们确定了对这一事件产生深远影响的变量，并允许利用控制权。然后，这允许通过促进或抑制有机硼金属转移来控制交叉偶联途径，从而产生 Suzuki-Miyaura 或 Mizoroki-Heck 产品。我们展示了这种金属转移开关如何用于级联交叉偶联/Diels-Alder 反应中的合成增益，提供硼酸化或非硼酸化碳环，包括类固醇类支架。
• Visible Light Induced Brønsted Acid Assisted Pd‐Catalyzed Alkyl Heck Reaction of Diazo Compounds and <i>N</i> ‐Tosylhydrazones
  作者：Ziyan Zhang、Nikita Kvasovs、Anastasiia Dubrovina、Vladimir Gevorgyan

  DOI：10.1002/anie.202110924

  日期：2022.1.3

  mild visible light-induced palladium-catalyzed alkyl Heck reaction of diazo compounds and N-tosylhydrazones is reported. This method features Brønsted acid assisted generation of hybrid palladium C(sp3)-centered radical intermediate and broad reaction scope, highlighting the diverse applicability and the potential utility of this protocol in late-stage functionalization.

  报道了重氮化合物和N-甲苯磺酰腙的温和可见光诱导的钯催化烷基 Heck 反应。该方法具有布朗斯台德酸辅助生成杂化钯C(sp 3 )中心自由基中间体和广泛的反应范围，突出了该方案在后期功能化中的多样化适用性和潜在效用。
• Iron-Catalyzed, Markovnikov-Selective Hydroboration of Styrenes
  作者：Xu Chen、Zhaoyang Cheng、Zhan Lu

  DOI：10.1021/acs.orglett.7b00227

  日期：2017.3.3

  A highly Markovnikov-selective, iron-catalyzed hydroboration of styrenes is reported using available oxazolinylphenyl picolinamide as the ligand to afford the branched hydroboration products with up to >50/1 b/l. This reaction is operationally simple and could be carried out in gram scale.

  据报道，使用可用的恶唑啉基苯基吡啶甲酸酰胺作为配体，对苯乙烯进行了高度马尔科夫尼科夫选择性铁催化的硼氢化反应，以提供最高> 50/1 b / l的支链硼氢化产物。该反应操作简单，可以以克为单位进行。
• Visible-Light-Driven Iron-Promoted Thiocarboxylation of Styrenes and Acrylates with CO₂
  作者：Jian-Heng Ye、Meng Miao、He Huang、Si-Shun Yan、Zhu-Bao Yin、Wen-Jun Zhou、Da-Gang Yu

  DOI：10.1002/anie.201707862

  日期：2017.11.27

  nest: The first thiocarboxylation of styrenes and acrylates with CO2 to generate important β-thioacids was realized by using visible light as a driving force and catalytic iron salts as promoters. This multicomponent reaction features broad substrate scope, mild reaction conditions, and high regio-, chemo-, and diasteroselectivity. Mechanistic studies indicate that a radical pathway can account for the

  一个人飞过了COO  - COOH的巢穴：利用可见光作为驱动力，并用催化铁盐作为促进剂，实现了苯乙烯和丙烯酸酯与CO 2的第一次硫代羧化反应，生成重要的β-硫代酸。这种多组分反应具有广泛的底物范围，温和的反应条件以及高的区域选择性，化学选择性和非对映选择性。机理研究表明，自由基途径可以解释异常的区域选择性。
• Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism
  作者：Wen Zhang、Song Lin

  DOI：10.1021/jacs.0c08532

  日期：2020.12.9

  variety of alkene functionalization reactions, most of which proceed via an anodic oxidation pathway. In this report, we further expand the scope of electrochemistry to the reductive functionalization of alkenes. In particular, the strategic choice of reagents and reaction conditions enabled a radical-polar crossover pathway wherein two distinct electrophiles can be added across an alkene in a highly

  电化学允许以受控方式直接访问反应中间体（自由基和离子），以实现选择性有机转化。这一特征已在各种烯烃官能化反应中得到证实，其中大部分是通过阳极氧化途径进行的。在本报告中，我们将电化学的范围进一步扩展到烯烃的还原功能化。特别是，试剂和反应条件的战略选择实现了自由基-极性交叉途径，其中可以以高度化学和区域选择性的方式将两种不同的亲电子试剂添加到烯烃上。具体来说，我们在分子间碳甲酰化、抗马尔科夫尼科夫加氢烷基化、烯烃的羧基化反应——文献中罕见的先例——通过电还原生成烷基自由基和碳负离子中间体。这些反应使用容易获得的起始材料（烷基卤化物、烯烃等）和简单、无过渡金属的条件，并显示出广泛的底物范围和良好的官能团耐受性。通过简单地改变反应介质，可以使用统一的方案来实现所有三种转化。这一发展为构建 Csp3-Csp3 键提供了新的途径。通过简单地改变反应介质，可以使用统一的方案来实现所有三种转化。这一发展为构建