3-ethyl-1-phenyl-1H-indole | 112817-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-ethyl-1-phenyl-1H-indole
• 英文别名: 3-Ethyl-1-phenylindole
• CAS: 112817-89-7
• 化学式: C₁₆H₁₅N
• 分子量: 221.302
• InChiKey: LEWSDGJTQNMAEU-UHFFFAOYSA-N

物化性质

• 沸点：
  358.6±25.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

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：
  0.12
• 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：

  3-ethyl-1-phenyl-1H-indole 在 三乙基硅烷 、 potassium tert-butylate 作用下， 以 neat (no solvent) 为溶剂， 反应 18.0h， 以66%的产率得到9-ethyl-9-methyl-9,10-dihydroacridine
  参考文献：
  名称：

  Grubbs–Stoltz试剂Et3SiH / KOtBu引发的N-芳基吲哚的新还原重排

  摘要：

  通过与三乙基硅烷和叔丁醇钾加热，N- Arylindoles以一种新型的重排方式转化为二氢ac啶。研究表明，该途径涉及（i）吲哚自由基阴离子的形成，然后吲哚C2-N键的断裂，以及（ii）钾离子依赖性氢原子转移步骤后的闭环反应。事实证明，“自由基陷阱”基片的意外行为非常有助于构建拟议的机制。

  DOI：

  10.1039/d0sc00361a
• 作为产物：
  描述：

  在 zinc(II) chloride 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 3.0h， 以126 mg的产率得到3-ethyl-1-phenyl-1H-indole
  参考文献：
  名称：

  钯催化的胺类脱氢生成胺。通过胺与芳肼的交叉偶联反应获得吲哚的自然路线

  摘要：

  AbstractH‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.magnified image

  DOI：

  10.1002/adsc.201300559

文献信息

• <i>tert-</i> Butyl Iodide Mediated Reductive Fischer Indolization of Conjugated Hydrazones
  作者：Yuta Ito、Masafumi Ueda、Norihiko Takeda、Okiko Miyata

  DOI：10.1002/chem.201504010

  日期：2016.2.18

  available N‐aryl conjugated hydrazones with tert‐butyl iodide has been developed. In this reaction, tert‐butyl iodide is used as anhydrous HI source, and the generated HI acts as a Brønsted acid and a reducing agent. This operationally simple method allows access to various indole derivatives. Furthermore, the procedure can be applied to the synthesis of biologically active compounds.

  已经开发出一种新型的，易于获得的N-芳基共轭与叔丁基碘化物的还原费歇尔吲哚化反应。在该反应中，叔丁基碘化物用作无水HI源，生成的HI用作布朗斯台德酸和还原剂。这种操作简单的方法允许使用各种吲哚衍生物。此外，该方法可以应用于生物活性化合物的合成。
• Divergent Reactivity in Palladium-Catalyzed Annulation with Diarylamines and α,β-Unsaturated Acids: Direct Access to Substituted 2-Quinolinones and Indoles
  作者：Rajesh Kancherla、Togati Naveen、Debabrata Maiti

  DOI：10.1002/chem.201501208

  日期：2015.6.8

  A palladium‐catalyzed CH activation strategy has been successfully employed for exclusive synthesis of a variety of 3‐substituted indoles. A [3+3] annulation for synthesizing substituted 2‐quinolinones was recently developed by reaction of α,β‐unsaturated carboxylic acids with diarylamines under acidic conditions. In the present work, an analogous [3+2] annulation is achieved from the same set of

  钯催化的CH活化策略已成功用于各种3取代的吲哚的独家合成。最近，通过α，β-不饱和羧酸与二芳基胺在酸性条件下反应，开发了一种用于合成取代的2-喹啉酮的[3 + 3]环。在目前的工作中，在基本条件下，从同一组起始原料中获得了类似的[3 + 2]环空，仅生成1,3-二取代的吲哚。机理研究表明，在反应条件下，邻pal合-π-配位-β-迁移插入-β-氢化物消除反应顺序是有效的。
• Synthesis of Indole Derivatives by [2 + 2] Photocycloaddition of Indoline-2-thiones with alkenes and photodesulfurization of indoline-2-thiones
  作者：Takehiko Nishio、Mitsuru Oka

  DOI：10.1002/hlca.19970800205

  日期：1997.3.24

  The photochemical synthesis of indole derivatives starting from the indoline-2-thiones 1 is described. Irradiation of indoline-2-thiones 1 in the presence of alkenes 3 gave 2-alkyl-3H-indoles 4–7 or 2-alkylindoles 8–22 through the ring cleavage of the intermediates, spirocyclic amino-thietanes, initially derived by [2 + 2] cycloaddition of the CS bond of 1 and the CC bond of 3. Irradiation of 1 in

  描述了从二氢吲哚-2-硫酮1开始的吲哚衍生物的光化学合成。二氢吲哚-2-硫酮的照射1在烯烃的存在下3，得到2-烷基-3- ħ -indoles 4 - 7或2-烷基吲哚8 - 22穿过中间体的环切割，螺环氨基thietanes，最初由衍生[ [2 + 2]的1个CS键和3的CC键的环加成。在三烷基胺26存在下辐照1可获得脱硫产物27 – 32和意外的3-烷基吲哚33 – 40。Ñ -Acylindoline -2-硫酮11 - p，得到去酰基化的产品，二氢吲哚-2-硫酮1A - b，和乙酯43在CDC1照射时通过γ-H提取由激发硫代酰胺S-原子3 / EtOH或苯/乙醇 氧类似物2a - d也经过分子内H提取，以类似方式得到吲哚2-2-酮2e - f和乙酯43。
• Synthesis of DPIE [2-(1,2-Diphenyl-1H-indol-3-yl)ethanamine] Derivatives and Their Regulatory Effects on Pro-Inflammatory Cytokine Production in IL-1β-Stimulated Primary Human Oral Cells
  作者：Jeongah Lim、Jihyoun Seong、Seunggon Jung、Tae-Hoon Lee、Eunae Kim、Sunwoo Lee

  DOI：10.3390/molecules27030899

  日期：——

  Interleukin-1 beta (IL-1β) has diverse physiological functions and plays important roles in health and disease. In this report, we focus on its function in the production of pro-inflammatory cytokines, including IL-6 and IL-8, which are implicated in several autoimmune diseases and host defense against infection. IL-1β activity is markedly dependent on the binding affinity toward IL-1 receptors (IL-1Rs). Several studies have been conducted to identify suitable small molecules that can modulate the interactions between 1L-1β and 1L-1R1. Based on our previous report, where DPIE [2-(1,2-Diphenyl-1H-indol-3-yl)ethanamine] exhibited such modulatory activity, three types of DPIE derivatives were synthesized by introducing various substituents at the 1, 2, and 3 positions of the indole group in DPIE. To predict a possible binding pose in complex with IL-1R1, a docking simulation was performed. The effect of the chemicals was determined in human gingival fibroblasts (GFs) following IL-1β induction. The DPIE derivatives affected different aspects of cytokine production. Further, a group of the derivatives enabled synergistic pro-inflammatory cytokine production, while another group caused diminished cytokine production compared to DPIE stimulation. Some groups displayed no significant difference after stimulation. These findings indicate that the modification of the indole site could modulate IL-1β:IL1R1 binding affinity to reduce or enhance pro-inflammatory cytokine production.

  白细胞介素-1β（IL-1β）在生理功能中扮演着多种角色，并在健康和疾病中起着重要作用。在这份报告中，我们关注它在产生促炎细胞因子中的功能，包括IL-6和IL-8，这些细胞因子与几种自身免疫疾病和宿主对抗感染有关。IL-1β的活性在很大程度上取决于其与IL-1受体（IL-1Rs）的结合亲和力。已经进行了多项研究，以确定可以调节IL-1β和IL-1R1之间相互作用的合适小分子。根据我们先前的报告，DPIE [2-(1,2-二苯基-1H-吲哚-3-基)乙胺]表现出这种调节活性，通过在DPIE的吲哚基的1、2和3位置引入各种取代基合成了三种DPIE衍生物。为了预测与IL-1R1复合物中可能的结合位姿，进行了对接模拟。在IL-1β诱导后，化学物质的影响在人牙龈成纤维细胞（GFs）中被确定。DPIE衍生物影响细胞因子产生的不同方面。此外，一组衍生物能够促进促炎细胞因子的产生，而另一组与DPIE刺激相比导致细胞因子产生减少。有些组在刺激后显示没有显著差异。这些发现表明，对吲哚位点的修改可以调节IL-1β：IL1R1结合亲和力，从而减少或增强促炎细胞因子的产生。
• Process for Producing an Aromatic Unsaturated Compound
  申请人：Wang Weiqi

  公开号：US20080221337A1

  公开（公告）日：2008-09-11

  The present invention provides a process for producing an aromatic unsaturated compound of the formula (4) wherein Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron withdrawing group, which comprises reacting (a) a compound of the formula (1) Ar—H  (1) wherein Ar has the same meaning as defined above with (b) a compound of the formula (2) wherein Y has the same meaning as defined above, and Z represents a lower alkoxy, or a compound of the formula (3) wherein Y and Z have the same meanings as defined above, in the presence of (c) an acid or a compound which generates a mineral acid by its hydrolysis.

  本发明提供了一种制备公式（4）的芳香不饱和化合物的方法，其中Ar代表可选择取代的芳香基团或可选择取代的杂环芳香基团，Y代表电子提取基团，包括以下步骤：(a)将公式（1）的化合物Ar-H（1）与(b)公式（2）的化合物反应，其中Y具有与上述定义相同的含义，Z代表低级烷氧基，或公式（3）的化合物，其中Y和Z具有与上述定义相同的含义，在(c)酸或通过其水解生成矿酸的化合物的存在下。