tert-butyl (2-(5-methoxy-1-methyl-1H-indol-3-yl)ethyl)carbamate

• 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 (2-(5-methoxy-1-methyl-1H-indol-3-yl)ethyl)carbamate
• 英文别名: tert-butyl N-[2-(5-methoxy-1-methylindol-3-yl)ethyl]carbamate
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: NTMRLPKKWXKNTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-(5-methoxy-1-methyl-1H-indol-3-yl)ethyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 为溶剂， 生成 5-Methoxy-1-N-methyltryptamin
  参考文献：
  名称：

  Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.

  DOI：

  10.1016/j.bmcl.2007.05.070
• 作为产物：
  描述：

  5-methoxy-3-(N,N-dimethylaminomethyl)-N-methylindole 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 ammonium acetate 、 氧气 、 三乙胺 、 苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 131.58h， 生成 tert-butyl (2-(5-methoxy-1-methyl-1H-indol-3-yl)ethyl)carbamate
  参考文献：
  名称：

  可见光介导的 3-(N,N-二甲基氨基甲基)-吲哚α-氧化成醛

  摘要：

  结果：我们使用光氧化还原系统（方案 1）开发了一种可见光介导的吲哚叔胺氧化成相应的醛类。基于Stern-Volmer图，提出了一系列淬火实验机理。上述方法可以获得吲哚醛衍生物，可用于合成具有生物活性特性的天然化合物，如 (-)-Vincorine。 [3]

  DOI：

  10.1002/ejoc.201801335

文献信息

• Nine-Step Enantioselective Total Synthesis of (−)-Vincorine
  作者：Benjamin D. Horning、David W. C. MacMillan

  DOI：10.1021/ja402933s

  日期：2013.5.1

  highly enantioselective total synthesis of the akuammiline alkaloid (-)-vincorine has been accomplished. A key element of the synthesis is a stereoselective organocatalytic Diels-Alder, iminium cyclization cascade sequence, which serves to construct the tetracyclic alkaloid core architecture in one step from simple achiral precursors. The challenging seven-membered azepanyl ring system is installed by way

  已经完成了 akuammiline 生物碱 (-)-vincorine 的简洁且高度对映选择性的全合成。该合成的一个关键要素是立体选择性有机催化 Diels-Alder、亚胺鎓环化级联序列，其用于从简单的非手性前体一步构建四环生物碱核心结构。具有挑战性的七元氮杂环系统是通过从酰基碲化物前体引发的单个电子介导的环化事件安装的。(-)-vincorine 的全合成是通过 9 个步骤和 9% 的总产率从市售起始材料中实现的。
• Diborylmethyl Group as a Transformable Building Block for the Diversification of Nitrogen‐Containing Molecules
  作者：Chiwon Hwang、Yeosan Lee、Minjae Kim、Younggyu Seo、Seung Hwan Cho

  DOI：10.1002/anie.202209079

  日期：2022.9.12

  We established an efficient protocol for the preparation of halo-diborylmethanes and their use in homologative coupling with nitrogen nucleophiles to generate various nitrogen-substituted diborylmethanes. The diborylmethyl group installed onto the nitrogen atom served as a versatile synthetic handle, allowing for the programmed diversification of nitrogen-containing molecules.

  我们建立了一个有效的方案，用于制备卤代二硼基甲烷及其与氮亲核试剂同源偶联以产生各种氮取代的二硼基甲烷。安装在氮原子上的二硼甲基基团可用作多功能合成手柄，允许含氮分子的程序化多样化。
• Chiral Bisamino-Ether Compounds, And Method of Preparation and Use Thereof
  申请人：JINAN UNIVERSITY

  公开号：US20220162219A1

  公开（公告）日：2022-05-26

  The present invention provides novel chiral bisamino-ether compounds, and method of preparation and use thereof. The chiral bisamino-ether compounds have the structure of formula (I). The method of preparation includes: using chiral aminomethanol compounds as starting materials to react with halogenated aryl compounds in the presence of a base to give a variety of chiral bisamino-ether compounds. The novel chiral bisamino-ether compounds can be used for asymmetric fluorocyclization of unsaturated heterocyclic compounds with excellent enantioselectivity and great potentials for industrial applications.
• [EN] CHIRAL BISAMINO-ETHER COMPOUNDS, AND METHOD OF PREPARATION AND USE THEREOF<br/>[FR] COMPOSÉS BISAMINO-ÉTHER CHIRAUX ET PROCÉDÉ DE PRÉPARATION ET D'UTILISATION ASSOCIÉ
  申请人：UNIV JINAN

  公开号：WO2020007017A1

  公开（公告）日：2020-01-09

  The present invention provides novel chiral bisamino-ether compounds, and method of preparation and use thereof. The chiral bisamino-ether compounds have the structure of formula (I). The method of preparation includes: using chiral aminomethanol compounds as starting materials to react with halogenated aryl compounds in the presence of a base to give a variety of chiral bisamino-ether compounds. The novel chiral bisamino-ether compounds can be used for asymmetric fluorocyclization of unsaturated heterocyclic compounds with excellent enantioselectivity and great potentials for industrial applications.
• Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
  作者：John I. Trujillo、Marvin J. Meyers、David R. Anderson、Shridhar Hegde、Matthew W. Mahoney、William F. Vernier、Ingrid P. Buchler、Kun K. Wu、Syaluan Yang、Susan J. Hartmann、David B. Reitz

  DOI：10.1016/j.bmcl.2007.05.070

  日期：2007.8

  A structure-activity relationship study was conducted on a series of tetrahydro-beta-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNF alpha production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity. (c) 2007 Elsevier Ltd. All rialuts reserved.