2-[6-(3-hydroxyprop-1-ynyl)-1,3-benzodioxol-5-yl]acetonitrile | 1365565-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-[6-(3-hydroxyprop-1-ynyl)-1,3-benzodioxol-5-yl]acetonitrile
• 英文别名: 2-(6-(3-hydroxyprop-1-yn-1-yl)benzo[d][1,3]dioxol-5-yl)acetonitrile
• CAS: 1365565-49-6
• 化学式: C₁₂H₉NO₃
• 分子量: 215.208
• InChiKey: UXKHHEUDIGMWLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[6-(3-hydroxyprop-1-ynyl)-1,3-benzodioxol-5-yl]acetonitrile 在 nickel(II) chloride hexahydrate 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 乙酸乙酯 为溶剂， 反应 0.08h， 生成 tert-butyl (2-(6-(3-hydroxypropyl)benzo[d][1,3]dioxol-5-yl)ethyl)carbamate
  参考文献：
  名称：

  Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support

  摘要：

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.

  DOI：

  10.1021/jo2025477
• 作为产物：
  描述：

  5-溴-6-溴甲基-1,3-苯并二氧杂环戊二烯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[6-(3-hydroxyprop-1-ynyl)-1,3-benzodioxol-5-yl]acetonitrile
  参考文献：
  名称：

  Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support

  摘要：

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.

  DOI：

  10.1021/jo2025477

文献信息

• Progress in Carbonylative [2+2+1] Cycloaddition: Utilization of a Nitrile Group as the π Component
  作者：Takashi Iwata、Fuyuhiko Inagaki、Chisato Mukai

  DOI：10.1002/anie.201305729

  日期：2013.10.11

  New tricks, old reactions: The treatment of 2‐(1,2‐propadienyl)phenylacetonitrile derivatives with a catalytic amount of [RhCl(CO)dppp}2] (dppp=1,3‐bis(diphenylphosphanyl)propane) under a CO atmosphere produced benzo[f]oxyindole derivatives (see scheme). This aza‐Pauson–Khand‐type reaction was applicable to aliphatic substrates, thus resulting in the formation of the azabicyclo[3.3.0]octadienone derivatives

  新的技巧，旧的反应：在催化条件下处理催化量为[RhCl（CO）dppp} 2 ]（dppp = 1,3-‐双（二苯基膦基）丙烷的2-（1,2-丙二烯基）苯基乙腈衍生物CO气氛下生成苯并[ f ]氧基吲哚衍生物（参见方案）。该aza-Pauson-Khand型反应适用于脂肪族底物，从而导致形成azabicyclo [3.3.0] octadienone衍生物。
• Synthesis of Dopamine and Serotonin Derivatives for Immobilization on a Solid Support
  作者：Erik Daa Funder、Anne Bjørnskov Jensen、Thomas Tørring、Anne Louise Bank Kodal、Ane Rebolledo Azcargorta、Kurt Vesterager Gothelf

  DOI：10.1021/jo2025477

  日期：2012.4.6

  The two important neurotransmitters dopamine and serotonin are synthesized with short PEG tethers and immobilized on a magnetic solid support. The tether is attached to the aromatic moiety of the neurotransmitters to conserve their original functional groups. This approach causes minimal alteration of the original structure with the aim of optimizing the immobilized neurotransmitters for aptamer selection by SELEX. For the dopamine derivative, the tether is attached to the aromatic core of a dopamine precursor by the Sonogashira reaction. For serotonin, a link to the indole core is introduced by a Claisen rearrangement from the allylated phenol moiety of serotonin. The tethers are azide-functionalized, which enables coupling to alkyne-modified magnetic beads. The coupling to the magnetic beads is quantified by UV spectroscopy using Fmoc-monitoring of the immobilized dopamine and serotonin derivatives.