sodium salt of 2-ethylmalononitrile | 34916-52-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: sodium salt of 2-ethylmalononitrile
• 英文别名: sodium ethylmalononitrile；sodium;2-ethylpropanedinitrile
• CAS: 34916-52-4
• 化学式: C₅H₅N₂*Na
• 分子量: 116.098
• InChiKey: UPURNILMSOILOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.58
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  sodium salt of 2-ethylmalononitrile 、 (E)-3-chloro-4-methyl-1-p-nitrophenylpent-1-ene 在 N,N-di-tert-butylnitroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 21.0h， 以73%的产率得到2-ethyl-2-<(E)-4'-methyl-1'-p-nitrophenylpent-2'-enyl>malononitrile
  参考文献：
  名称：

  Barker, Steven D.; Norris, Robert K., Australian Journal of Chemistry, 1983, vol. 36, # 3, p. 527 - 544

  摘要：

  DOI：
• 作为试剂：
  描述：

  9,10-二碘蒽 在 硝酸 、 sodium salt of 2-ethylmalononitrile 作用下， 以 氘代二甲亚砜 、 乙酸酐 、 甲苯 为溶剂， 反应 48.83h， 生成 9-iodo-2-nitro-9,10-dihydro-9,10-ethanoanthracene
  参考文献：
  名称：

  Reduction of Bridgehead Halogens by an Intramolecular Electron Transfer Radical Mechanism

  摘要：

  Reactions of 9,10-dibromo- and 9,10-diiodo-2-nitro-9,10-ethano-9,10-dihydroanthracene (10 and 11, respectively) with the tertiary carbanions, 1, 3, 5, and 7-9, proceed exclusively by reduction at the bridgehead with no substitution products being observed. It is proposed that the reduction process occurs by a radical chain mechanism including an intramolecular electron transfer step and beta-hydrogen abstraction from alkyl substituents on the participating carbanions. These ethanoanthracenes contain halogens at bridgehead positions that are meta- and para-benzylic relative to an aromatic nitro group, thus allowing the determination of the relative reactivities of the two benzylic sites within the same molecule. Quantitative studies on the reaction of 11 with sodium salts of 2-ethylmalononitrile and diethyl 2-ethylmalonate reveal that the reduction process is regioselective, with reduction occurring more readily at the benzylic bridgehead position para to the nitro group than at the corresponding meta-benzylic position. The ratio of meta:para reduction products, determined for the reaction of the diiodide 11 with several carbanions, was in the range 1:(1.6 +/- 0.2). This ratio contrasts with the differences in rate constants (approximately 2 orders of magnitude) determined for other nitrobenzylic systems, known to undergo S(RN)1 substitution reactions with the same nucleophiles. These differences in the ratio of rate constants of regioselective reduction compared with those observed for substitution reactions is discussed in terms of the C-X bond at a bridgehead position lying orthogonal to the plane of the nitroaryl group. As a result of this geometry, the rate of intramolecular electron transfer is significantly reduced and the ratio of para-benzylic to meta-benzylic reactivity differs only by a factor of less than 2.

  DOI：

  10.1021/jo00122a030

文献信息

• Steric and electronic limitations of the SRN1 reaction between p-nitrobenzylic substrates and tertiary carbanions
  作者：Bruce D Jacobs、Soon-Jae Kwon、Leslie D Field、Robert K Norris、David Randles、Karen Wilson、Timothy A Wright

  DOI：10.1016/s0040-4039(00)98673-8

  日期：1985.1
• Barker, Steven D.; Norris, Robert K., Australian Journal of Chemistry, 1983, vol. 36, # 1, p. 81 - 95
  作者：Barker, Steven D.、Norris, Robert K.

  DOI：——

  日期：——