tert-butyl 3-(2-bromoethyl)-1H-indole-1-carboxylate | 131829-28-2

• 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: tert-butyl 3-(2-bromoethyl)-1H-indole-1-carboxylate
• 英文别名: N-BOC-3-(2-bromoethyl)indole；tert-butyl 3-(2-bromoethyl)indole-1-carboxylate
• CAS: 131829-28-2
• 化学式: C₁₅H₁₈BrNO₂
• 分子量: 324.217
• InChiKey: UNVROTRVHZAYKF-UHFFFAOYSA-N

物化性质

• 沸点：
  399.7±34.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  tert-butyl 3-(2-bromoethyl)-1H-indole-1-carboxylate 在 potassium carbonate 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 23.0h， 生成 (S)-(2-((2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl)(1-phenylethyl)amino)-2-oxoethyl)dimethylsulfonium bromide
  参考文献：
  名称：

  Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide

  摘要：

  We present here a synthetic route for the access to a series of diverse indoloazocine derivatives through selective epoxidation of chiral sulfonium salt 4, which reacts with diverse aromatic and aliphatic aldehydes to give trans-glycidic amides, followed by an intramolecular electrophilic aromatic substitution promoted by Cu(OTf)(2) giving the desired heterocyclic compound in a high chemical yield. Using this strategy, the total synthesis of (S,R)-(+)-norbalasubramide was achieved. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.068
• 作为产物：
  描述：

  色醇 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl 3-(2-bromoethyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Biomimetic Approach to Perophoramidine and Communesin via an Intramolecular Cyclopropanation Reaction

  摘要：

  Starting from tryptamine 4 and isatin 5, a biomimetic approach to the pentacyclic substructure 1 of perophoramidine and communesin was developed. The key steps were to create a stable three/six bicyclic system 2 on the 2,3-double bond of an indole derivative 3 by an intramolecular cyclopropanation, followed by ring opening of the resulting cyclopropane ring with the in situ generated amine group of an aniline.

  DOI：

  10.1021/ol0607138

文献信息

• Peptidomimetic analogues of an Arg-Trp-x-x-Trp motif responsible for interaction of translocase MraY with bacteriophage ϕX174 lysis protein E
  作者：Rachel V. Kerr、Julia A. Fairbairn、Andrew T. Merritt、Timothy D.H. Bugg

  DOI：10.1016/j.bmc.2021.116502

  日期：2021.12

  also found in several cationic antimicrobial peptides. Analogues of Arg-Trp-octyl ester, found previously to show antimicrobial activity, were tested for antimicrobial activity, with Lys-Trp-oct (MIC50 P. fluorescens 5 µg/mL) and Arg-Trp-decyl ester (MIC50 P. fluorescens 3 µg/mL) showing enhanced antimicrobial activity. Synthesis and testing of α-helix peptidomimetic analogues for this motif revealed

  Translocase MraY 是噬菌体 φX174 裂解蛋白 E 的靶标，它通过大肠杆菌MraY的 Phe-288 和 Glu-287 介导的蛋白质-蛋白质相互作用以及蛋白质 E 上的 Arg-Trp-xx-Trp 基序进行相互作用，在几种阳离子抗菌肽中发现。先前发现显示抗微生物活性的 Arg-Trp-辛酯类似物用 Lys-Trp-oct（MIC 50 P. fluorescens 5 µg/mL）和 Arg-Trp-癸酯（MIC 50 P . fluorescens 3 µg/mL) 显示出增强的抗菌活性。该基序的 α-螺旋拟肽类似物的合成和测试表明其抗菌活性有所提高（MIC 50 大肠杆菌4–7 µg/mL) 用于含有两个芳香族取代基的类似物，模拟 Arg-Trp-xx-Trp 基序，以及一种此类肽模拟物的 MraY 抑制 (IC 50 140 µM)。使用 Alamar Blue
• Dynamic multiligand catalysis: A polar to radical crossover strategy expands alkyne carboboration to unactivated secondary alkyl halides
  作者：Shin-Ho Kim-Lee、Pablo Mauleón、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1016/j.chempr.2021.06.002

  日期：2021.8

  triggers cooperative polar/radical pathways in a single catalytic cycle. This strategy has been applied to address a restricting limitation inherent to Cu-catalyzed B2pin2-carboboration of alkynes—the very low reactivity of the intermediate vinyl-Cu(I) species, which renders conventional methods ineffective with alkyl electrophiles other than simple primary halides. The crossover strategy enabled by

  我们描述了基于前所未有的动态多配体配位池的 Cu 催化的双重策略，该池在单个催化循环中触发合作的极性/自由基途径。该策略已被应用于解决 Cu 催化的 B 2 pin 2固有的限制性限制-炔烃的碳硼化——中间体乙烯基-Cu(I) 物质的反应性非常低，这使得传统方法对烷基亲电试剂无效，而不是简单的伯卤化物。通过有机金属中间体中的配体交换实现的交叉策略克服了这一反应性问题，将碳硼化的范围扩大到未活化的仲烷基卤化物，并开辟了获得立体定义的四取代乙烯基硼酸酯的新途径。该方法具有区域选择性和立体选择性，显示出优异的官能团耐受性，并允许在任一反应伙伴处掺入复杂的碳环和杂环片段。
• Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex
  作者：Jin Xie、Jian Li、Vanessa Weingand、Matthias Rudolph、A. Stephen K. Hashmi

  DOI：10.1002/chem.201602939

  日期：2016.8.26

  A practical protocol for a photocatalyzed alkyl‐Heck‐like reaction of unactivated alkyl bromides and different alkenes promoted by dinuclear gold photoredox catalysis in the presence of an inorganic base is reported. Primary, secondary, and tertiary unactivated alkyl bromides with β‐hydrogen can be applied. Esters, aldehydes, ketones, nitriles, alcohols, heterocycles, alkynes, alkenes, ethers, and

  报导了在无机碱存在下，由双核金光氧化还原催化促进的未活化烷基溴和不同烯烃的光催化烷基-Heck-样反应的实用方案。可以使用带有β-氢的伯，仲和叔未活化烷基溴。酯，醛，酮，腈，醇，杂环，炔烃，烯烃，醚和卤素部分均具有良好的耐受性。除1,1-二芳基烯烃外，还可以使用甲硅烷基醚和烯酰胺，这进一步增加了反应的合成潜力。温和的反应条件，广泛的底物范围和出色的官能团耐受性为合成化学家提供了理想的工具，甚至可以用于挑战复杂天然产物的后期修饰。
• Somatostatin analogue compounds
  申请人：——

  公开号：US20040019069A1

  公开（公告）日：2004-01-29

  Compounds having somatostatin activity of the following Formula I, 1 wherein, R 1 is aryl, substituted-aryl, and aryl-(lower-alkyl)-; R 2 is lower alkyl, amino substituted lower alkyl, -carboxy-(lower-alkyl), -carbamic acid-(lower-alkyl) and -carboxy-(lower-alkyl)-aryl; and R 3 and R 4 are independently, lower-alkyl, aryl, substituted-aryl, (substituted-aryl)-(lower-alkyl)-, heteroaryl, (heteroaryl)-(lower-alkyl)-, substituted-heteroaryl, (substituted heteroaryl)-(lower-alkyl)-, heterocyclic, heterocyclic-(lower-alkyl)-, substituted-heterocyclic, (substituted-heterocylic)-(lower alkyl)-, -carboxy-(lower-alkyl), and -carboxy-(lower-alkyl)-aryl; or a pharmaceutically acceptable, ester, ether, or salt thereof; methods for their use; and preparation.

  具有生长抑素活性的化合物，其具有以下公式I， 1 其中， R 1 是芳基，取代芳基，和芳基-(低碳烷基)-； R 2 是低碳烷基，氨基取代低碳烷基，-羧基-(低碳烷基)，-氨基甲酸-(低碳烷基)和-羧基-(低碳烷基)-芳基；和 R 3 和 R 4 是独立地，低碳烷基，芳基，取代芳基，(取代芳基)-(低碳烷基)-，杂芳基，(杂芳基)-(低碳烷基)-，取代杂芳基，(取代杂芳基)-(低碳烷基)-，杂环，杂环-(低碳烷基)-，取代杂环，(取代杂环)-(低碳烷基)-，-羧基-(低碳烷基)，和-羧基-(低碳烷基)-芳基；或其药用可接受的，酯，醚，或盐；其使用方法；及其制备。
• Application of a novel design paradigm to generate general nonpeptide combinatorial scaffolds mimicking beta turns: synthesis of ligands for somatostatin receptors
  作者：Dona Chianelli、Yong-Chul Kim、Dmitriy Lvovskiy、Thomas R Webb

  DOI：10.1016/j.bmc.2003.08.022

  日期：2003.11

  practical method for the design of scaffolds exhibiting drug-like properties that are suitable for the display of peptide pharmacophores. The synthesis of various synthons of 7'-hydroxy-2',3'-dihydro-1'H,2H,5H-spiro[imidazolidine-4,4'-quinoline]-2,5-dione (1) and methods for the introduction of several mimics of amino acid side-chains are described. This method is exemplified by derivatives that show

  模仿生物活性肽的非肽化合物对于许多临床适应症是理想的。我们报告了一种新型的实用方法，用于设计展示药物样特性的支架，该特性适合于肽药效团的展示。7'-羟基-2'，3'-二氢-1'H，2H，5H-螺[咪唑烷-4,4'-喹啉] -2,5-二酮的各种合成子的合成（1）及其制备方法描述了几种氨基酸侧链模拟物的引入。该方法以对生长抑素2型受体表现出激动剂活性的衍生物为例。