4-(benzofuran-2-yl)morpholine | 1195901-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-(benzofuran-2-yl)morpholine
• 英文别名: 4-(1-benzofuran-2-yl)morpholine
• CAS: 1195901-19-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: OETXGKQGMCFMES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-苯并呋喃 在 正丁基锂 、 copper dichloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成 4-(benzofuran-2-yl)morpholine
  参考文献：
  名称：

  Copper-Catalyzed Electrophilic Amination of Heteroarenes via C–H Alumination

  摘要：

  A highly efficient Cu-catalyzed electrophilic amination reaction of readily available heteroarenes with O-benzoyl hydroxylamines via a one-pot C-H alumination is reported. The reactions were catalyzed using 1 mol % of CuCl to afford various heteroaryl amines in good to excellent yields. The direct C-H lithiation/transalumination of heteroarenes and catalytic amination sequence can be performed in a single vessel on gram scales.

  DOI：

  10.1021/acs.joc.5b01863

文献信息

• Copper-Catalyzed Electrophilic Amination of Heteroarenes and Arenes by CH Zincation
  作者：Stacey L. McDonald、Charles E. Hendrick、Qiu Wang

  DOI：10.1002/anie.201311029

  日期：2014.4.25

  Direct amination of heteroarenes and arenes has been achieved in a one‐pot CH zincation/copper‐catalyzed electrophilic amination procedure. This amination method provides an efficient and rapid approach to access a diverse range of heteroaromatic and aromatic amines including those previously inaccessible using CH amination methods. The mild reaction conditions and good functional‐group compatibility

  杂芳烃和芳烃的直接胺化已经在一锅C - H锌化/铜催化的亲电胺化过程中实现。这种胺化方法提供了一种高效、快速的方法来获得各种杂芳胺和芳香胺，包括以前使用 C - H 胺化方法无法获得的胺。温和的反应条件和良好的官能团相容性证明了其在合成重要且复杂的胺类方面的巨大潜力。
• Preparation of Heterocyclic Amines by an Oxidative Amination of Zinc Organometallics Mediated by CuI: A New Oxidative Cycloamination for the Preparation of Annulated Indole Derivatives
  作者：Marcel Kienle、Andreas J. Wagner、Cora Dunst、Paul Knochel

  DOI：10.1002/asia.201000367

  日期：2011.2.1

  Functionalized heterocyclic zinc reagents are easily aminated by an oxidative amination reaction of zinc amidocuprates prepared from various lithium amides. For the oxidation step, PhI(OAc)2 proved to be the best reagent. The required heterocyclic zinc organometallics can be prepared either by direct metalation, by magnesium insertion in the presence of ZnCl2, or by transmetalation of a suitable magnesium

  官能化的杂环锌试剂很容易通过由各种锂酰胺制备的酰胺基铜酸锌的氧化胺化反应进行胺化。对于氧化步骤，PhI（OAc）2被证明是最好的试剂。所需的杂环锌有机金属化合物可通过直接金属化，在ZnCl 2存在下通过镁插入或通过合适的镁试剂的金属转移来制备。此外，我们报道了涉及分子内氧化胺化反应的新的闭环反应。该反应允许制备含有呋喃，噻吩或吲哚环的四环杂环。
• Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters
  作者：Christian A. Malapit、Margarida Borrell、Michael W. Milbauer、Conor E. Brigham、Melanie S. Sanford

  DOI：10.1021/jacs.9b13531

  日期：2020.4.1

  synthetic chemists. This report describes the development of a nickel-catalyzed decarbonylative reaction that couples (hetero)aromatic esters with a broad scope of amines to form (hetero)aryl amine products. The successful realization of this transformation was predicated on strategic design of the cross-coupling partners (phenol esters and silyl amines) to preclude conventional reactivity that forms

  羧酸衍生物与胺反应形成酰胺键是上个世纪有机合成中应用最广泛的转化。它的效用受到起始材料的广泛可用性以及酰胺键形成的动力学和热力学驱动力的驱动。因此，在战略上偏离酰胺键形成的羧酸衍生物和胺之间的新反应的发明对于合成化学家来说既是挑战也是机遇。本报告描述了镍催化脱羰反应的发展，该反应将（杂）芳族酯与多种胺偶联以形成（杂）芳基胺产品。
• BORONIC ACID BEARING LIPHAGANE COMPOUNDS AS INHIBITORS OF P13K- a AND/OR B
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20150051173A1

  公开（公告）日：2015-02-19

  Compounds with unique liphagane meroterpenoid scaffold having boronic acid functionality in the skeleton are described (formula 1) together with pharmacological potential of these compounds as anticancer agents. A method of preparation and inhibiting the activity of phosphoinositide-3-kinase (PI3K-alpha and beta) has been presented. In particular, the invention describes a method of inhibiting PI3K isoforms, wherein the compounds are novel structures based on liphagane scaffold with unique boronic acid functionality. The methods and uses thereof are described herein this invention.

  描述了具有硼酸功能性的独特脂肪环萜类化合物骨架的化合物（式1），以及这些化合物作为抗癌药物的药理潜力。提出了一种制备方法和抑制磷脂酰肌醇-3-激酶（PI3K-alpha和beta）活性的方法。具体而言，本发明描述了一种抑制PI3K同工型的方法，其中这些化合物是基于脂肪环萜类骨架具有独特硼酸功能性的新结构。本发明描述了这些方法及其用途。
• [EN] PBD ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTÉRIENS DE TYPE PBD
  申请人：KING'S COLLEGE LONDON

  公开号：WO2017098257A1

  公开（公告）日：2017-06-15

  The invention relates to pyrrolobenzodiazepines compounds (PBDs) and to pharmaceutically acceptable salts thereof, which are useful as medicaments, in particular, to treat bacterial infections. The PBDs are compounds of formula (I): and salts and solvates thereof; wherein: dotted lines indicates the optional presence of a double bond; X, X1, X2, X3 and X4 are connecting functional groups; L is C1-12 alkylene; R4, R5 and R6 are independently selected from phenylene, cyclopentanylene, cyclohexanylene, 5 - to 9 -membered heteroarylene and 5 - to 6-membered hetereocyclylene groups, and these groups are optionally substituted with up to three optional substituent groups; R7 is selected from N(C1-6 alkyl)(C1-6alkyl), 5 - to 6-membered nitrogen-containing hetereocyclyl groups, a monosaccharide moiety and an amino monosaccharide moiety wherein these groups are optionally substituted; and R8 and R9 either together form a double bond, or are selected from H and OR14, or R8 is a prodrug moiety and R9 is OR14; m is 0 or 1; with the proviso that when X4 is C(O)NH then the up to three optional substituents of R7 are not selected from (CH2)k -CO2R12; with the proviso that when X4 is (CH2)tO then R4 is not phenylene, m is 1 and R6 is not a 5 - to 9 -membered heteroarylene; and with the proviso that when X4 is C(O)NH or NHC(O) that R4 and/or R6 is not 5 - to 9 -membered heteroarylene.

  该发明涉及吡咯苯二氮杂环烷化合物（PBD）及其药用可接受盐，其作为药物具有治疗细菌感染的功效。PBD是具有以下结构式（I）的化合物：及其盐和溶剂化物；其中：虚线表示双键的可选存在；X、X1、X2、X3和X4是连接的功能基团；L为C1-12烷基；R4、R5和R6分别选自苯环、环戊烷基、环己烷基、5-至9-成员杂芳烃基和5-至6-成员杂环烷基，这些基团可选地被高达三个可选取代基团取代；R7选自N（C1-6烷基）（C1-6烷基）、5-至6-成员含氮杂环基团、单糖基团和氨基单糖基团，其中这些基团可选地被取代；R8和R9要么一起形成双键，要么选自H和OR14，或者R8是前药基团且R9是OR14；m为0或1；但是当X4为C（O）NH时，R7的高达三个可选取代基团不选自（CH2）k-CO2R12；但是当X4为（ ）tO时，R4不是苯环，m为1且R6不是5-至9-成员杂芳烃基；但是当X4为C（O）NH或NHC（O）时，R4和/或R6不是5-至9-成员杂芳烃基。