1-(4-chlorophenyl)-1-(2-pentynyloxy)-2-nitroethane | 144347-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorophenyl)-1-(2-pentynyloxy)-2-nitroethane
• 英文别名: 1-Chloro-4-(2-nitro-1-pent-2-ynoxyethyl)benzene
• CAS: 144347-58-0
• 化学式: C₁₃H₁₄ClNO₃
• 分子量: 267.712
• InChiKey: PHTLQDCSIBXQSM-UHFFFAOYSA-N

物化性质

• 沸点：
  404.7±45.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-1-(2-pentynyloxy)-2-nitroethane 在 异氰酸苯酯 、 三乙胺 作用下， 以 苯 为溶剂， 以88%的产率得到6-(4-chlorophenyl)-3-ethyl-4H,6H-furo<3,4-c>isoxazole
  参考文献：
  名称：

  A facile synthesis of furo[3,4-c]isoxazoles: precursors to 3,4-disubstituted isoxazoles

  摘要：

  Nitrile oxide-olefin cycloaddition reactions deliver heterocyclic products with a wide variety of functionality and provide a particularly powerful means of preparing substituted isoxazoles by the intermolecular 1,3-dipolar cycloaddition of a nitrile oxide with a monosubstituted alkyne to give a preponderance of the 3,5-disubstituted isoxazole. In this study, an extension of the intramolecular nitrile oxide-olefin cycloaddition reaction is reported for the facile synthesis of furo[3,4-c]isoxazoles (5) which are in tum shown to be useful precursors to 3,4-disubstituted or 3,4,5-trisubstituted isoxazole derivatives (6). The method consists of a high-yield preparation of a broad spectrum of furo[3,4-c]isoxazoles by intramolecular nitrile oxide-alkyne cycloaddition of acetylenic nitro ethers (3), in turn prepared by Michael addition of various propargylic alkoxides (2) to appropriate nitro olefins (1).

  DOI：

  10.1021/jo00050a027
• 作为产物：
  描述：

  2-戊炔-1-醇 、 1-nitro-2-(4-chlorophenyl)ethylene 在 正丁基锂 作用下， 生成 1-(4-chlorophenyl)-1-(2-pentynyloxy)-2-nitroethane
  参考文献：
  名称：

  A facile synthesis of furo[3,4-c]isoxazoles: precursors to 3,4-disubstituted isoxazoles

  摘要：

  Nitrile oxide-olefin cycloaddition reactions deliver heterocyclic products with a wide variety of functionality and provide a particularly powerful means of preparing substituted isoxazoles by the intermolecular 1,3-dipolar cycloaddition of a nitrile oxide with a monosubstituted alkyne to give a preponderance of the 3,5-disubstituted isoxazole. In this study, an extension of the intramolecular nitrile oxide-olefin cycloaddition reaction is reported for the facile synthesis of furo[3,4-c]isoxazoles (5) which are in tum shown to be useful precursors to 3,4-disubstituted or 3,4,5-trisubstituted isoxazole derivatives (6). The method consists of a high-yield preparation of a broad spectrum of furo[3,4-c]isoxazoles by intramolecular nitrile oxide-alkyne cycloaddition of acetylenic nitro ethers (3), in turn prepared by Michael addition of various propargylic alkoxides (2) to appropriate nitro olefins (1).

  DOI：

  10.1021/jo00050a027

文献信息

• A facile synthesis of furo[3,4-c]isoxazoles: precursors to 3,4-disubstituted isoxazoles
  作者：Hyung Jin Kim、Jae Hyun Lee、Marilyn M. Olmstead、Mark J. Kurth

  DOI：10.1021/jo00050a027

  日期：1992.11

  Nitrile oxide-olefin cycloaddition reactions deliver heterocyclic products with a wide variety of functionality and provide a particularly powerful means of preparing substituted isoxazoles by the intermolecular 1,3-dipolar cycloaddition of a nitrile oxide with a monosubstituted alkyne to give a preponderance of the 3,5-disubstituted isoxazole. In this study, an extension of the intramolecular nitrile oxide-olefin cycloaddition reaction is reported for the facile synthesis of furo[3,4-c]isoxazoles (5) which are in tum shown to be useful precursors to 3,4-disubstituted or 3,4,5-trisubstituted isoxazole derivatives (6). The method consists of a high-yield preparation of a broad spectrum of furo[3,4-c]isoxazoles by intramolecular nitrile oxide-alkyne cycloaddition of acetylenic nitro ethers (3), in turn prepared by Michael addition of various propargylic alkoxides (2) to appropriate nitro olefins (1).