allyl 2-hydroxy-3-nitropropyl ether

• 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: allyl 2-hydroxy-3-nitropropyl ether
• 英文别名: 1-Nitro-3-prop-2-enoxypropan-2-ol；1-nitro-3-prop-2-enoxypropan-2-ol
• 化学式: C₆H₁₁NO₄
• 分子量: 161.158
• InChiKey: YUOOFSVUCXBVLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  烯丙基缩水甘油醚 在 cerium(IV) triflate 、 sodium dodecyl-sulfate 、 sodium nitrite 作用下， 反应 0.17h， 以75%的产率得到allyl 2-hydroxy-3-nitropropyl ether
  参考文献：
  名称：

  Micellar media for the efficient ring opening of epoxides with CN–, N3–, NO3–, NO2–, SCN–, Cl– and Br– catalyzed with Ce(OTf)4

  摘要：

  引入胶束介质以高效地打开环氧化物，使用如CN⁻、N3⁻、NO3⁻、NO2⁻、SCN⁻、Br⁻和Cl⁻等亲核盐，并用Ce(OTf)₄催化。这种方法是在温和反应条件下合成不同β-取代醇的高效程序。与SCN⁻的反应是一种简单的程序，用于高产率制备环氧硫化物。

  DOI：

  10.1039/b211697a

文献信息

• Micellar media for the efficient ring opening of epoxides with CN–, N3–, NO3–, NO2–, SCN–, Cl– and Br– catalyzed with Ce(OTf)4
  作者：Nasser Iranpoor、Habib Firouzabadi、Marzieh Shekarize

  DOI：10.1039/b211697a

  日期：2003.2.11

  Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN−, N3−, NO3−, NO2−, SCN−, Br− and Cl−, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN− is an easy procedure for the high yielding preparation of epoxy sulfides.

  引入胶束介质以高效地打开环氧化物，使用如CN⁻、N3⁻、NO3⁻、NO2⁻、SCN⁻、Br⁻和Cl⁻等亲核盐，并用Ce(OTf)₄催化。这种方法是在温和反应条件下合成不同β-取代醇的高效程序。与SCN⁻的反应是一种简单的程序，用于高产率制备环氧硫化物。
• Synthesis and characterization of a novel nano-Fe3O4-copoly[(styrene/acrylic acid)/grafted ethylene oxide and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azido alcohols and β-nitro alcohols
  作者：Ali Reza Kiasat、Mina Daei、Seyyed Jafar Saghanezhad

  DOI：10.1007/s11164-015-2043-0

  日期：2016.2

  A facile method was developed for the synthesis of β-azido alcohols and β-nitro alcohols in the presence of a novel nano-Fe3O4-copoly[(styrene/acrylic acid)/grafted ethylene oxide (nano-Fe3O4-PS-Co-[PAA-g-PEG]) as a phase-transfer catalyst in water. The catalyst was characterized with IR, SEM, and TGA. This procedure offers several advantages, including excellent regioselectivity, high yields, short reaction times, a recyclable catalyst, easy separation of the catalyst through an external magnet, and easy workup .

  在新型纳米氧化铁-聚[（苯乙烯/丙烯酸）/接枝环氧乙烷（nano-Fe3O4-PS-Co-[PAA-g-PEG]）作为相转移催化剂存在下，开发了一种在水中合成β-叠氮醇和β-硝基醇的简便方法。该催化剂通过红外光谱、扫描电镜和热重分析进行了表征。该方法具有多个优点，包括极佳的区域选择性、产率高、反应时间短、催化剂可回收利用、催化剂易于通过外部磁铁分离以及易于加工。
• <sup>15</sup>N nuclear polarization in the reactions of diallyl ether with nitrogen dioxide
  作者：Robert P. Claridge、Ross W. Millar、John H. Ridd

  DOI：10.1139/cjc-77-5-6-647

  日期：——
• Synthesis and characterization of a novel nanomagnetic phase-transfer catalyst and its application to regioselective synthesis of β-azido and β-nitro alcohols in water
  作者：N. Ayashi、M. Fallah-Mehrjardi、A. R. Kiasat

  DOI：10.1134/s1070428017060069

  日期：2017.6

  Fe3O4 nanoparticles through hexane-1,6-diyldicarbamate linker afforded a powerful and reusable heterogeneous phase-transfer catalysis which was successfully used for regioselective ring opening of epoxides with azide and nitrite anions in aqueous medium. The new catalyst can readily be recovered by simple magnetic decantation and recycled several times without appreciable loss of catalytic activity

  通过己烷-1,6-二基二氨基甲酸酯连接基将聚乙二醇取代的1-甲基咪唑溴化铵固定在磁性Fe 3 O 4纳米颗粒的表面上，提供了有力且可重复使用的异相转移催化，该催化转移反应已成功用于环氧化物的区域选择性开环水性介质中的叠氮化物和亚硝酸根阴离子。通过简单的磁倾析法可以很容易地回收新催化剂，并循环使用几次，而不会明显丧失催化活性。