4-bromo-pent-4-enylamine | 484027-09-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 4-bromo-pent-4-enylamine
• 英文别名: 5-amino-2-bromo-1-pentene；4-Bromopent-4-en-1-amine
• CAS: 484027-09-0
• 化学式: C₅H₁₀BrN
• 分子量: 164.045
• InChiKey: WBZRFRTZKGKSBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-pent-4-enylamine 在 18-冠醚-6 、 2,6-二叔丁基-4-甲基苯酚 、 双(三甲基硅烷基)氨基钾 、 sodium sulfate 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 27.33h， 生成 methyl (Z)-3-[(3aR,7aR)-1-(4-bromopent-4-enyl)-2-oxo-3,3a,6,7-tetrahydroindol-7a-yl]prop-2-enoate
  参考文献：
  名称：

  Total synthesis of (±)-isophellibiline

  摘要：

  The total synthesis of (+/-)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of amidodioxin, an intramolecular Heck reaction and a 6 pi-electrocyclic ring closure of a dienoic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.161
• 作为产物：
  描述：

  2-(4-bromo-pent-4-enyl)-isoindole-1,3-dione 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以97%的产率得到4-bromo-pent-4-enylamine
  参考文献：
  名称：

  自由基介导的乙烯基胺化：温和的一般吡咯烷基烯胺合成

  摘要：

  描述了自由基介导的乙烯基胺化的完整范围，使用了乙烯基自由基对偶氮甲碱氮的5-外-trig环化。焦点主要集中在N，N-二烷基烯胺上，因为它们的亲核性使其成为使用氧化还原条件合成最具挑战性的烯胺。这些研究为该策略的广泛应用建立了一些令人鼓舞的先例。

  DOI：

  10.1016/j.tet.2003.04.003

文献信息

• Free radical-mediated vinyl amination: a mild, general pyrrolidinyl enamine synthesis
  作者：Benjamin M. Nugent、Amie L. Williams、E.N. Prabhakaran、Jeffrey N. Johnston

  DOI：10.1016/j.tet.2003.04.003

  日期：2003.11

  The complete scope of free radical-mediated vinyl amination is described, using 5-exo-trig cyclizations of vinyl radicals to the nitrogen of azomethines. The focus is primarily on N,N-dialkyl enamines since their nucleophilicity renders them the most challenging enamines to synthesize using redox conditions. These studies establish several encouraging precedents for the broader application of this

  描述了自由基介导的乙烯基胺化的完整范围，使用了乙烯基自由基对偶氮甲碱氮的5-外-trig环化。焦点主要集中在N，N-二烷基烯胺上，因为它们的亲核性使其成为使用氧化还原条件合成最具挑战性的烯胺。这些研究为该策略的广泛应用建立了一些令人鼓舞的先例。
• Free Radical-Mediated Vinyl Amination:  Access to <i>N,N</i>-Dialkyl Enamines and Their β-Stannyl and β-Thio Derivatives
  作者：Erode N. Prabhakaran、Benjamin M. Nugent、Amie L. Williams、Kristen E. Nailor、Jeffrey N. Johnston

  DOI：10.1021/ol027064u

  日期：2002.11.1

  The first examples of free radical-mediated vinyl amination are described by nonconventional vinyl radical addition to azomethine nitrogen. This new vinyl amination protocol is mild and provides convenient synthetic access to nonstabilized N,N-dialkyl enamines and tandem bond-forming processes.
• Enantioselective Halocyclization Using Reagents Tailored for Chiral Anion Phase-Transfer Catalysis
  作者：Yi-Ming Wang、Jeffrey Wu、Christina Hoong、Vivek Rauniyar、F. Dean Toste

  DOI：10.1021/ja305795x

  日期：2012.8.8

  A chiral anion phase-transfer system for enantioselective halogenation is described. Highly insoluble, ionic reagents were developed as electrophilic bromine and iodine sources, and application of this system to o-anilidostyrenes afforded halogenated 4H-3,1-benzoxazines with excellent yield and enantioselectivity.
• Total synthesis of (±)-isophellibiline
  作者：Raymond L. Funk、Johannes Belmar

  DOI：10.1016/j.tetlet.2011.10.161

  日期：2012.1

  The total synthesis of (+/-)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of amidodioxin, an intramolecular Heck reaction and a 6 pi-electrocyclic ring closure of a dienoic acid. (C) 2011 Elsevier Ltd. All rights reserved.