1-Ethoxycarbonyl-2,3-dihydro-1H-indole | 61589-17-1

• 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-Ethoxycarbonyl-2,3-dihydro-1H-indole
• 英文别名: ethyl indoline-1-carboxylate；Ethyl-indolin-1-carboxylat；2,3-dihydro-indole-1-carboxylic acid ethyl ester；ethyl 2,3-dihydroindole-1-carboxylate
• CAS: 61589-17-1
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD03385555
• 分子量: 191.23
• InChiKey: FEFTZWVEDKFHFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Ethoxycarbonyl-2,3-dihydro-1H-indole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以18%的产率得到吲哚啉
  参考文献：
  名称：

  Mild and selective deprotection of carbamates with Bu4NF

  摘要：

  A new mild method allowing the removal of carbamates using TBAF in THF is reported. Reactions were performed on indole, indoline, N-methyl aniline, aniline and tryptamine derivatives. The observed selectivity according to the carbamates or the substrates is discussed. A mechanism is postulated. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.07.071
• 作为产物：
  描述：

  ethyl 2-iodoethyl(2-iodophenyl)carbamate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三(2-呋喃基)膦 、 caesium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 6.0h， 以82%的产率得到1-Ethoxycarbonyl-2,3-dihydro-1H-indole
  参考文献：
  名称：

  钯催化的Csp2分子内还原性交叉偶联？Csp3键形成

  摘要：

  甲Pd催化的还原效率的交叉偶联反应没有金属还原剂来构造CSP 2  CSP 3键已经报道。Pd IV络合物被认为是关键的中间体，随后通过双氧化加成和双还原性消除，使Pd 0 / II / IV参与一次转化，从而产生交叉偶联产物。从Pd II到Pd IV的氧化加成被部分证明是通过底物的自氧化而没有其他氧化剂的自由基过程。此外，通过XPS分析证明溶剂是该转化的还原剂。

  DOI：

  10.1002/chem.201403093

文献信息

• Studies on Cognitive Enhancing Agents. III. Antiamnestic and Antihypoxic Activities of a Series of l-Bicycloaryl-2-(.OMEGA.-aminoalkoxy)ethanols.
  作者：Satoshi ONO、Tetsuo YAMAFUJI、Hisaaki CHAKI、Hajime MORITA、Yozo TODO、Naomi OKADA、Mutsuko MAEKAWA、Kazunori KITAMURA、Masaru TAI、Hirokazu NARITA

  DOI：10.1248/cpb.43.1492

  日期：——

  2-(2-Aminoethoxy)-1-hydroxyethyl derivatives of bicyclic arenes) naphthalene, thianaphthene, benzofuran, and indole) were prepared and screened for antiamnestic (AA) and antihypoxic (AH) activities which were evaluated by measuring the reversing potency in electroconvulsion-induced amnesia and the protective effect against hypoxia, respectively, in mice. Compound 3o, 1-(benzo[b]thiophen-5-yl)-2-(2-diethylaminoethoxy)ethanol, showed the best AA and AH activity profile, being superior to our prototype compound, 2-(2-dimethylaminoethoxy)-1-phenylethanol (1). Elongation of the ethylene linkage in the side chain of 3o to 3- and 4-carbon moiethies brought about a significant decrease in AH activity. Compound 3o was further investigated for its protective effect against Co2-induced memory impairment and for acute toxicity in mice. It is ten-fold more potent than tacrine in the amnesia-reversal assay and is considerably less toxic than tacrine.

  双环芳烃（萘、噻吊、苯并呋喃和吲哚）的2-(2-氨基乙氧基)-1-羟乙基衍生物被制备并筛选出具有抗遗忘（AA）和抗缺氧（AH）活性的化合物。这些活性通过测定逆转电休克诱导的遗忘和保护小鼠免受缺氧影响的效力来评估。化合物3o，1-(苯并[b]噻吩-5-基)-2-(2-二乙基氨基乙氧基)乙醇，显示出最佳的AA和AH活性特征，优于我们的原型化合物，2-(2-二甲基氨基乙氧基)-1-苯乙醇（1）。在3o的侧链中延长乙烯链接到3-和4-碳单元，显著降低了AH活性。化合物3o进一步研究了其对Co2诱导记忆障碍的保护作用和在小鼠中的急性毒性。在逆转遗忘试验中，其效力是他克林的十倍，并且毒性远低于他克林。
• [EN] ALLOSTERIC BINDING COMPOUNDS<br/>[FR] COMPOSÉS DE LIAISON ALLOSTÉRIQUES
  申请人：UNIV AARHUS

  公开号：WO2010094289A1

  公开（公告）日：2010-08-26

  The present invention relates to allosteric binding compounds of formula (I), especially for the treatment of CNS disorders, together with pharmaceutical compositions and methods of treatment including these compounds.

  本发明涉及具有公式(I)的变构结合化合物，尤其用于治疗中枢神经系统疾病，以及包含这些化合物的药物组合物和治疗方法。
• Chemoselective Synthesis of Carbamates using CO₂as Carbon Source
  作者：Daniel Riemer、Pradipbhai Hirapara、Shoubhik Das

  DOI：10.1002/cssc.201600521

  日期：2016.8.9

  Synthesis of carbamates directly from amines using CO2 as the carbon source is a straightforward and sustainable approach. Herein, we describe a highly effective and chemoselective methodology for the synthesis of carbamates at room temperature and atmospheric pressure. This methodology can also be applied to protect the amino group in amino acids and peptides, and also to synthesize important pharmaceuticals

  使用CO 2作为碳源直接从胺合成氨基甲酸酯是一种简单而可持续的方法。在此，我们描述了一种在室温和大气压下合成氨基甲酸酯的高效且化学选择性的方法。该方法还可用于保护氨基酸和肽中的氨基，也可用于合成重要的药物。
• ALLOSTERIC BINDING COMPOUNDS
  申请人：Neubauer Henrik Amtoft

  公开号：US20120095048A1

  公开（公告）日：2012-04-19

  The present invention relates to allosteric binding compounds of formula (I), especially for the treatment of CNS disorders, together with pharmaceutical compositions and methods of treatment including these compounds.

  本发明涉及具有公式(I)的变构结合化合物，尤其用于治疗中枢神经系统疾病，以及包含这些化合物的药物组合物和治疗方法。
• Cp*Co^III-Catalyzed C(7)–H Bond Annulation of Indolines with Alkynes
  作者：Rajib Mandal、Bholanath Garai、Basker Sundararaju

  DOI：10.1021/acs.joc.1c00713

  日期：2021.7.16

  biologically essential pyrroloquinolinones has been developed under Cp*CoIII catalysis, which involves a cascade reaction of C(7)–H alkenylation with alkynes followed by nucleophilic addition. A wide variety of internal alkynes including enyne, diyne, and ynamide and more challenging terminal alkynes were successfully employed for the annulation in good to excellent yield with high regioselectivity.

  在 Cp*Co III催化下开发了一种合成生物必需吡咯并喹啉酮的有效方案，该方案涉及 C(7)-H 烯基化与炔烃的级联反应，然后是亲核加成。包括烯炔、二炔和炔酰胺在内的多种内部炔烃和更具挑战性的末端炔烃被成功用于环化，收率良好，具有高区域选择性。