甲基烯丙基(萘-1-基甲基)氨基甲酸酯 | 1334031-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 甲基烯丙基(萘-1-基甲基)氨基甲酸酯
• 英文名称: methyl allyl(naphthalen-1-ylmethyl)carbamate
• 英文别名: methyl N-(naphthalen-1-ylmethyl)-N-prop-2-enylcarbamate
• CAS: 1334031-94-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: SERUXCWOVKIOHO-UHFFFAOYSA-N

物化性质

• 沸点：
  394.3±22.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  甲基烯丙基(萘-1-基甲基)氨基甲酸酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium aluminium tetrahydride 、 sodium acetate 作用下， 以 四氢呋喃 、 苯甲腈 为溶剂， 反应 3.5h， 生成 萘替芬
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z
• 作为产物：
  描述：

  (氯甲基)萘 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 24.5h， 生成 甲基烯丙基(萘-1-基甲基)氨基甲酸酯
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z

文献信息

• Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines
  作者：Patrícia Prediger、Laís Ferreira Barbosa、Yves Génisson、Carlos Roque Duarte Correia

  DOI：10.1021/jo201105z

  日期：2011.10.7

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.