4-氰基-2-氟-2-硝基丁酸乙酯 | 110683-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-氰基-2-氟-2-硝基丁酸乙酯
• 英文名称: ethyl 4-cyano-2-fluoro-2-nitrobutyrate
• 英文别名: Ethyl 4-cyano-2-fluoro-2-nitrobutanoate
• CAS: 110683-81-3
• 化学式: C₇H₉FN₂O₄
• 分子量: 204.158
• InChiKey: MPJIEXRJXYAHDD-UHFFFAOYSA-N

物化性质

• 沸点：
  315.9±42.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-氰基-2-氟-2-硝基丁酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-fluoro-4-nitrobutanenitrile
  参考文献：
  名称：

  Chemistry of novel compounds with a multifunctional carbon structure. 5. Molecular design of versatile building blocks for aliphatic monofluoro molecules by manipulation of multifunctional carbon structure

  摘要：

  DOI：

  10.1021/jo00284a017
• 作为产物：
  描述：

  ethyl 4-cyano-2-nitrobutanoate 在 potassium fluoride 、 过氯酰氟 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以100%的产率得到4-氰基-2-氟-2-硝基丁酸乙酯
  参考文献：
  名称：

  The first versatile and practical building blocks equivalent to the synthon of monofluoromethylene dicarbanion

  摘要：

  DOI：

  10.1021/jo00231a053

文献信息

• The first versatile and practical building blocks equivalent to the synthon of monofluoromethylene dicarbanion
  作者：Yoshio Takeuchi、Kazuhiro Nagata、Toru Koizumi

  DOI：10.1021/jo00231a053

  日期：1987.10
• The first general and efficient method for the synthesis of tertiary alkyl fluorides
  作者：Yoshio Takeuchi、Arihiro Kanada、Shunichi Kawahara、Toru Koizumi

  DOI：10.1021/jo00065a005

  日期：1993.6

  The first general and regioselective method for the synthesis of a wide variety of tertiary alkyl fluorides [R1(R2)C(F)R3] has been developed. This novel method involves the successive introduction of three different alkyl groups onto fluorine-bearing prototertiary carbon fragments.
• First Electronic Investigation of the Structure of Alkenes Compatible to Carbon Radicals Bearing a Single Fluorine Atom
  作者：Yoshio Takeuchi、Shun-ichi Kawahara、Takanori Suzuki、Toru Koizumi、Hiroyuki Shinoda

  DOI：10.1021/jo951622j

  日期：1996.1.1

  In order to look into the electronic course of the Michael addition of alpha-fluorocarbon radical to alkenes, theoretical MO calculations and experiments were attempted. The SOMO values and atomic charges for the alpha-carbon radical of ethyl beta-phenylpropionate (4a) and that of the alpha-fluoro analog (4b) and HOMO and LUMO values and atomic charges for three representative alkenes, acrylonitrile (6), styrene (7), and propene (8), were calculated using 6-31G and 6-31G* methods. The results are as follows: (i) In the case of simple radicals such as 4a, interaction between the SOMO of radicals and the LUMO of alkenes seems dominant, and therefore, 4a should react with 6 more readily than 7 or 8. (ii) Those radicals having an electron-withdrawing group (EWG) such as fluorine become more electrophilic, considering the energy level differences between the SOMO of radicals and the HOMO and LUMO of alkenes, (iii) The energy level difference between the SOMO of 4b and the HOMO of 7 is smaller than that between the SOMO of 4b and the HOMO of 6 or 8, and further, the terminal carbon atom in 7 is more negatively charged than that in 6 or 8. Therefore, electrophilic radicals such as 4b should be more reactive toward 7 than 6 or 8, On the basis of these predictions, the denitrative alkylations of alpha-fluoro-alpha-nitroalkanoic esters (1a and 1b) with 7, having no EWG but being conjugated with an aromatic ring, were found to give the alpha-alkylated alpha-nuoro esters (3e and 3d, respectively) in much improved yield when compared with those reactions with 6 having a conjugated EWG. This result provides an important synthetic strategy toward useful monofluoro molecules.
• TAKEUCHI, YOSHIO;NAGATA, KAZUHIRO;KOIZUMI, TORU, J. ORG. CHEM., 54,(1989) N3, C. 5453-5459
  作者：TAKEUCHI, YOSHIO、NAGATA, KAZUHIRO、KOIZUMI, TORU

  DOI：——

  日期：——
• TAKEUCHI, Y.;NAGATA, K.;KOIZUMI, T., J. ORG. CHEM., 52,(1987) N 22, 5061-5063
  作者：TAKEUCHI, Y.、NAGATA, K.、KOIZUMI, T.

  DOI：——

  日期：——