4-fluoro-4-nitrobut-1-ene | 1355020-79-9

• 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: 4-fluoro-4-nitrobut-1-ene
• 英文别名: 4-Fluoro-4-nitrobut-1-ene
• CAS: 1355020-79-9
• 化学式: C₄H₆FNO₂
• 分子量: 119.096
• InChiKey: PXYSKNVZBDCGBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-fluoro-4-nitrobut-1-ene 、 1-苯基-2-丙烯基-1-酮 在 [RuH2(PPh3)4] 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以42%的产率得到4-fluoro-4-nitro-1-phenylhept-6-en-1-one
  参考文献：
  名称：

  [RuH2(PPh3)4]-Catalyzed Michael Addition Reaction of α-Fluoronitroalkanes

  摘要：

  The Michael addition reactions of alpha-fluoronitroalkanes with various electron-deficient olefins were realized by catalysis of low-valence ruthenium species through C-sp3-H activation, providing a useful way to construct a fluorinated quaternary carbon center. The reactions were carried out under neutral conditions, affording the desired products in moderate to excellent yields.

  DOI：

  10.1055/s-0032-1317526
• 作为产物：
  描述：

  4-nitrobut-1-ene 在 potassium hydroxide 、 Selectfluor 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 1.17h， 以73%的产率得到4-fluoro-4-nitrobut-1-ene
  参考文献：
  名称：

  氟化硝基化合物的亨利反应

  摘要：

  据报道，氟化硝基化合物与各种芳族醛和氟化脂肪族醛的亨利（硝基醛醇）反应生成带有氟化季碳中心的β-氟-β-硝基醇。通过X射线单晶分析确定2-氟-2-硝基-1-（4-硝基苯基）-3-苯基丙醇（5bf）的主要非对映异构体的相对构型。

  DOI：

  10.1016/j.jfluchem.2011.09.004

文献信息

• Henry reaction of fluorinated nitro compounds
  作者：Huawei Hu、Yangen Huang、Yong Guo

  DOI：10.1016/j.jfluchem.2011.09.004

  日期：2012.1

  The Henry (nitroaldol) reaction of fluorinated nitro compounds with various aromatic aldehydes and a fluorinated aliphatic aldehyde to give β-fluoro-β-nitroalcohols which bearing a fluorinated quaternary carbon center was reported. The relative configuration of the major diastereoisomer of 2-fluoro-2-nitro-1-(4-nitrophenyl)-3-phenylpropanol (5bf) was determined by X-ray single crystal analysis.

  据报道，氟化硝基化合物与各种芳族醛和氟化脂肪族醛的亨利（硝基醛醇）反应生成带有氟化季碳中心的β-氟-β-硝基醇。通过X射线单晶分析确定2-氟-2-硝基-1-（4-硝基苯基）-3-苯基丙醇（5bf）的主要非对映异构体的相对构型。
• Michael Addition Reaction of Fluorinated Nitro Compounds
  作者：Feng Huan、Huawei Hu、Yangen Huang、Qingyun Chen、Yong Guo

  DOI：10.1002/cjoc.201100412

  日期：2012.4

  The Michael addition reactions of fluorinated nitro compounds with electron deficient olefins to give γ‐fluoro‐γ‐nitro‐esters, nitriles and ketones which bear a fluorinated quaternary carbon center were reported. The reactions were promoted by TMG, affording the desired adducts in acceptable to good yields.

  据报道，氟化硝基化合物与缺电子的烯烃的迈克尔加成反应生成了带有氟化季碳中心的γ-氟-γ-硝基酯，腈和酮。通过TMG促进反应，以可接受的收率至良好的收率提供所需的加合物。
• [RuH2(PPh3)4]-Catalyzed Michael Addition Reaction of α-Fluoronitroalkanes
  作者：Xianjin Yang、Yong Guo、Qi Wang、Qing-Yun Chen

  DOI：10.1055/s-0032-1317526

  日期：——

  The Michael addition reactions of alpha-fluoronitroalkanes with various electron-deficient olefins were realized by catalysis of low-valence ruthenium species through C-sp3-H activation, providing a useful way to construct a fluorinated quaternary carbon center. The reactions were carried out under neutral conditions, affording the desired products in moderate to excellent yields.
• Enantioselective Synthesis of <i>cis</i>- and <i>trans</i>-Cycloheptyl β-Fluoro Amines by Sequential aza-Henry Addition/Ring-Closing Metathesis
  作者：Jade A. Bing、Jeffrey N. Johnston

  DOI：10.1021/acs.orglett.2c04285

  日期：2023.2.17

  The synthesis of 7-membered carbocyclic β-fluoroamines is accomplished by a combination of the enantioselective aza-Henry reaction of aliphatic N-Boc imines and ring-closing metathesis. Use of reductive denitration gives both diastereomers of the β-fluoro amine carbocycle, each with high enantiomeric excess.

  7元碳环β-氟胺的合成是通过脂肪族N -Boc亚胺的对映选择性氮杂-亨利反应和闭环复分解反应的结合来完成的。使用还原脱硝得到β-氟胺碳环的两种非对映体，每种都具有高对映体过量。