2-methyl-2-nitro-3-propyloxirane | 1434076-21-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-methyl-2-nitro-3-propyloxirane
• CAS: 1434076-21-7
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: XYPSRBJPPDVWQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2-nitro-3-propyloxirane 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以89%的产率得到2,5-dimethyl-3,6-dipropylpyrazine
  参考文献：
  名称：

  Nitroepoxides as Versatile Precursors to 1,4-Diamino Heterocycles

  摘要：

  Nitroepoxides are easily transformed into 1,4-diamino heterocycles such as quinoxalines and pyrazines by treatment with 1,2-benzenediamines and ammonia, respectively. Additionally, related saturated heterocycles, such as piperazines and tetrahydroquinoxalines, can be accessed by treatment with 1,2-diamines and a reducing agent. These transformations are efficient, provide access privileged, bioactive structures, and produce minimal waste.

  DOI：

  10.1021/ol500444z
• 作为产物：
  描述：

  (E)-2-nitrohex-2-ene 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 以68%的产率得到2-methyl-2-nitro-3-propyloxirane
  参考文献：
  名称：

  Nitroepoxides as Versatile Precursors to 1,4-Diamino Heterocycles

  摘要：

  Nitroepoxides are easily transformed into 1,4-diamino heterocycles such as quinoxalines and pyrazines by treatment with 1,2-benzenediamines and ammonia, respectively. Additionally, related saturated heterocycles, such as piperazines and tetrahydroquinoxalines, can be accessed by treatment with 1,2-diamines and a reducing agent. These transformations are efficient, provide access privileged, bioactive structures, and produce minimal waste.

  DOI：

  10.1021/ol500444z

文献信息

• One-pot three-component protocol for the synthesis of substituted 2-aminothiazoles
  作者：Shanshan Guo、Donghong Zhao、Yue Zhu、Yongping Yu、Wenteng Chen、Guolin Zhang

  DOI：10.1080/00397911.2017.1350275

  日期：2017.10.2

  ABSTRACT Substituted 2-aminothiazoles have been synthesized from α-nitro-epoxides, cyanamide, and sodium sulfide through a facile, three-component, and ecofriendly protocol with good to excellent yields. This reaction was achieved at room temperature without any additives. A possible mechanism has also been proposed. GRAPHICAL ABSTRACT

  摘要 由 α-硝基环氧化物、氰胺和硫化钠通过简便、三组分和环保的方案合成了取代的 2-氨基噻唑，收率良好。该反应是在室温下完成的，没有任何添加剂。还提出了一种可能的机制。图形概要
• A multi-component synthesis of <i>N</i>-substituted 2-amino-3-cyano pyrroles <i>via</i> ring-opening of nitroepoxides
  作者：Xingyu Liu、Zhuang Nie、Jiaan Shao、Wenteng Chen、Yongping Yu

  DOI：10.1039/c7nj04584k

  日期：——

  A multi-component synthesis of N-substituted 2-amino-3-cyano pyrroles from nitroepoxides, amines and malononitrile has been demonstrated. The reaction proceeded well for a wide range of nitroepoxides and amines under mild conditions without transition metal catalysis via the formation of three new bonds.

  已经证明了由硝基环氧化物，胺和丙二腈多组分合成N-取代的2-氨基-3-氰基吡咯。对于各种硝基环氧化物和胺，该反应在温和条件下进行得很好，而没有通过形成三个新键的过渡金属催化。
• Efficient and facile strategy to substituted 2-aminothiazoles via ring opening of α-nitroepoxides
  作者：Yue Zhu、Qilin Wang、Haofan Luo、Guolin Zhang、Yongping Yu

  DOI：10.1016/j.tet.2018.09.005

  日期：2018.12

  A novel and efficient reaction has been developed to synthesize a set of substituted 2-aminothiazoles from α-nitroepoxides and ammonium thiocyanate. This reaction could proceed smoothly at mild condition, to afford products for a wide range of substrates with good to excellent yields. A possible mechanism has also been proposed.

  已经开发了一种新颖而有效的反应，以由α-硝基环氧化物和硫氰酸铵合成一组取代的2-氨基噻唑。该反应可以在温和的条件下平稳进行，从而以良好或优异的产率提供用于多种底物的产物。还提出了一种可能的机制。
• Facile, efficient synthesis of polysubstituted thiazoles via α-nitroepoxides and thioureas
  作者：Donghong Zhao、Shanshan Guo、Xiao Guo、Guolin Zhang、Yongping Yu

  DOI：10.1016/j.tet.2016.05.010

  日期：2016.9

  An efficient synthesis of 2,4,5-trisubstituted thiazoles via the reaction of α-nitroepoxides and thioureas under mild conditions has been developed. This reaction proceeded well at room temperature, to afford products in excellent yields for a wide range of substrate, and a possible mechanism has also been proposed.

  已经开发了在温和条件下通过α-硝基环氧化物与硫脲反应有效合成2,4,5-三取代噻唑的方法。该反应在室温下进行得很好，从而为广泛的底物提供了具有优异收率的产物，并且还提出了一种可能的机理。
• A three-component one-pot synthesis of penta-substituted pyrroles via ring opening of α-nitroepoxides
  作者：Donghong Zhao、Yue Zhu、Shanshan Guo、Wenteng Chen、Guolin Zhang、Yongping Yu

  DOI：10.1016/j.tet.2017.03.074

  日期：2017.5

  A novel and facile one-pot reaction has been developed to synthesize a variety of penta-substituted pyrroles from α-nitroepoxides, primary amines and dialkyl acetylenedicarboxylates under the conditions without catalyst. Furthermore, the controlled experiments has been performed and a possible mechanism has also been proposed.

  已经开发了新颖且简便的一锅反应，以在无催化剂的条件下由α-硝基环氧化物，伯胺和乙酰二羧酸二烷基酯合成多种五取代的吡咯。此外，已经进行了受控实验并且还提出了可能的机制。