trifluoroacetohydroximoyl bromide etherate | 14533-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trifluoroacetohydroximoyl bromide etherate
• 英文别名: ethoxyethane;2,2,2-trifluoro-N-hydroxyethanimidoyl bromide
• CAS: 14533-30-3
• 化学式: C₂HBrF₃NO*C₄H₁₀O
• 分子量: 266.058
• InChiKey: LKRAGWPHKJJTLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trifluoroacetohydroximoyl bromide etherate 在 sodium methylate 作用下， 生成 三氟乙腈氧化物
  参考文献：
  名称：

  Tanaka, Kiyoshi; Suzuki, Takashi; Maeno, Seiji, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1535 - 1538

  摘要：

  DOI：
• 作为产物：
  描述：

  trifluoroacetaldehyde oxime 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 trifluoroacetohydroximoyl bromide etherate
  参考文献：
  名称：

  Tanaka, Kiyoshi; Suzuki, Takashi; Maeno, Seiji, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1535 - 1538

  摘要：

  DOI：

文献信息

• Exo/Endo Stereoselectivity in 1,3-Dipolar Cycloaddition of Trifluoroacetonitrile Oxide and -nitrilimine with Bicyclic Olefins
  作者：Kiyoshi Tanaka、Hideyuki Masuda、Keiryo Mitsuhashi

  DOI：10.1246/bcsj.59.3901

  日期：1986.12

  their cycloadditions with norbornadienes. The nitrile oxide was subjected to the cycloaddition with 2,3-disubstituted norbornadienes to evaluate the effect of the substituents on the exo/endo stereoselectivity. The electron-withdrawing substituents tend to favor the formation of the exo-adducts.

  三氟乙腈氧化物和 N-苯基-C-（三氟甲基）腈亚胺与降冰片烯环加成，导致外加合物的唯一形成，而在它们与降冰片二烯的环加成中观察到内加合物的伴随形成。将腈氧化物与 2,3-二取代降冰片二烯进行环加成，以评估取代基对外/内立体选择性的影响。吸电子取代基倾向于有利于外加合物的形成。
• An Unusual Cyclization of Trifluoroacetohydroximoyl and -hydrazonoyl Bromides with Malononitrile
  作者：Kiyoshi Tanaka、Takashi Suzuki、Seiji Maeno、Keiryo Mitsuhashi

  DOI：10.1246/bcsj.60.4480

  日期：1987.12

  Trifluoroacetohydroximoyl bromide etherate (1) reacted with an excess of malononitrile in the presence of sodium methoxide, giving a fused isoxazolopyridine 3, participated by two molecules of malononitrile, along with the conventional isoxazole 2. Similar concomitant formation of 7 and the fused pyrazolopyridines 8 was also recognized from the hydrazonoyl bromides 6 and their product ratio was found to depend on the reaction conditions, particularly on the concentration of malononitrile used.

  在甲醇钠存在下，三氟乙酰基溴羟亚甲酰醚（1）与过量的丙二腈反应，生成了由两分子丙二腈参与的融合异噁唑吡啶 3 和传统的异噁唑 2。从肼基溴化物 6 中也同样生成了 7 和融合的吡唑并吡啶 8，而且发现它们的产物比例取决于反应条件，特别是所用丙二腈的浓度。
• A Competition between 1,3-Dipolar Cycloaddition and Substitution of Trifluoroacetonitrile Oxide
  作者：Kiyoshi Tanaka、Hideyuki Masuda、Keiryo Mitsuhashi

  DOI：10.1246/bcsj.58.2061

  日期：1985.7

  Trifluoroacetonitrile oxide reacted with conjugated olefins such as styrenes, indenes, and acyclic conjugated dienes to give not only the cycloadduct but also its linear isomeric oxime. Methyl or phenyl group attached to the unsaturated carbon of the dipolarophiles was found to favor the formation of oxime. Such a concomitant reaction was interpreted in terms of a competition between a concerted cycloaddition

  三氟乙腈氧化物与共轭烯烃如苯乙烯、茚和无环共轭二烯反应，不仅生成环加合物，还生成其线性异构肟。发现与亲偶极体的不饱和碳相连的甲基或苯基有利于肟的形成。这种伴随反应被解释为协同环加成和通过氧化腈的亲电攻击进行的两步取代之间的竞争。还研究了环状共轭二烯的类似竞争，发现产品的竞争比例取决于环的大小。