1-allyl-4,6-dibromo-3-hydroxyindolin-2-one | 700359-43-9

• 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-allyl-4,6-dibromo-3-hydroxyindolin-2-one
• 英文别名: 4,6-dibromo-3-hydroxy-3-prop-2-enyl-1H-indol-2-one
• CAS: 700359-43-9
• 化学式: C₁₁H₉Br₂NO₂
• 分子量: 347.006
• InChiKey: JBJBDEQSHXDKLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allyl-4,6-dibromo-3-hydroxyindolin-2-one 在 2,6-二甲基吡啶 、 三(二甲氨基)锍二氟三甲基硅酸 、 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 100.5h， 生成 (+/-)-4,6-dibromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole
  参考文献：
  名称：

  Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones

  摘要：

  Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (+/-)-donaxaridine, as well as (+/-)-convolutamydines A and E , was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.031
• 作为产物：
  描述：

  1-acetyl-4,6-dibromo-3-hydroxy-2-methoxy-indoline 在 4 A molecular sieve D(+)-10-樟脑磺酸 、 溴 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 125.5h， 生成 1-allyl-4,6-dibromo-3-hydroxyindolin-2-one
  参考文献：
  名称：

  Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones

  摘要：

  Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (+/-)-donaxaridine, as well as (+/-)-convolutamydines A and E , was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.031

文献信息

• [EN] SIMPLE ORGANIC MOLECULES AS CATALYSTS FOR PRACTICAL AND EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF AMINES AND ALCOHOLS<br/>[FR] MOLÉCULES ORGANIQUES SIMPLES EN TANT QUE CATALYSEURS POUR LA SYNTHÈSE ÉNANTIOSÉLECTIVE PRATIQUE ET EFFICACE D'AMINES ET D'ALCOOLS
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2013131043A1

  公开（公告）日：2013-09-06

  The present invention provides organic molecules and methods thereof for reactions between organoboron reagents and double bonds, such as imines or carbonyls, to stereoselectively provide chiral products including amines and alcohols, entities useful for the preparation of biologically active molecules.

  本发明提供了有机分子及其方法，用于有机硼试剂与双键（如亚胺或羰基）之间的反应，以立体选择性地提供手性产物，包括胺和醇等实体，用于制备具有生物活性的分子。
• SIMPLE ORGANIC MOLECULES AS CATALYSTS FOR PRACTICAL AND EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF AMINES AND ALCOHOLS
  申请人：Trustees of Boston College

  公开号：US20150057451A1

  公开（公告）日：2015-02-26

  The present invention provides organic molecules and methods thereof for reactions between organoboron reagents and double bonds, such as imines or carbonyls, to stereoselectively provide chiral products including amines and alcohols, entities useful for the preparation of biologically active molecules.

  本发明提供了有机分子及其方法，用于有机硼试剂与双键（如亚胺或羰基）之间的反应，以立体选择性地提供手性产物，包括胺和醇等实体，这些实体对于制备生物活性分子非常有用。
• Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis
  作者：Giancarlo Cravotto、Giovanni B. Giovenzana、Giovanni Palmisano、Andrea Penoni、Tullio Pilati、Massimo Sisti、Federica Stazi

  DOI：10.1016/j.tetasy.2006.11.021

  日期：2006.11

  The absolute configuration of (+)-convolutamydine A 1 isolated from Amathia convoluta has been unambiguously established as (R) by enantioselective synthesis, based on chiral auxiliary-directed pi-face discrimination in an allyl metal addition to (1R,2S,5R)-8-phenylmenthyl ester 7. For an independent and unequivocal proof, the absolute stereochemistry of synthetic precursor 11 en route to 1 was determined by X-ray crystallography. (c) 2006 Published by Elsevier Ltd.
• A Hg(ClO₄)₂·3H₂O Catalyzed Sakurai–Hosomi Allylation of Isatins and Isatin Ketoimines Using Allyltrimethylsilane
  作者：Zhong-Yan Cao、Yan Zhang、Cong-Bin Ji、Jian Zhou

  DOI：10.1021/ol202705g

  日期：2011.12.16

  It is reported that Hg(ClO4)(2)center dot 3H(2)O could efficiently activate the cheap but less reactive allyltrimethylsilane for the allylation of isatins or isatin ketoimines, with catalyst loading down to 0.1 mol %. This is the first example of Sakurai-Hosomi allylation of ketoimines using allyltrimethylsilane. A rare example of chiral mercury catalysis is also reported.
• US9328061B2
  申请人：——

  公开号：US9328061B2

  公开（公告）日：2016-05-03