isopentylmalonitrile | 153597-70-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: isopentylmalonitrile
• 英文别名: isopentylmalononitrile；(3-methylbutyl)malononitrile；2-cyano-5-methylhexanenitrile；2-(3-Methylbutyl)propanedinitrile
• CAS: 153597-70-7
• 化学式: C₈H₁₂N₂
• mdl: MFCD06215017
• 分子量: 136.197
• InChiKey: SBQFSZUDZNNUFG-UHFFFAOYSA-N

物化性质

• 沸点：
  243.5±13.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isopentylmalonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 13.0h， 以31%的产率得到3,5-diamino-4-isopentylpyrazole
  参考文献：
  名称：

  4-烷基吡唑类肝醇脱氢酶抑制剂的合成

  摘要：

  通过对一组 4-烷基吡唑的范德华表面分子静电势进行形状分析的理论研究预测，4-异戊基衍生物是肝醇脱氢酶的良好抑制剂。因此，新的 4-异戊基和已知的 4-辛基吡唑已通过新的路线制备。异戊基衍生物已被测试为马肝醇脱氢酶的抑制剂，给出了理论研究预测的结果。

  DOI：

  10.1002/ardp.19943270507
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 五氯化磷 作用下， 生成 isopentylmalonitrile
  参考文献：
  名称：

  Hessler, Journal of the American Chemical Society, 1913, vol. 35, p. 991

  摘要：

  DOI：

文献信息

• Sodium Borohydride as the Only Reagent for the Efficient Reductive Alkylation­ of Malononitrile with Ketones and Aldehydes
  作者：Robert E. Sammelson、Jason C. Dunham、Adam D. Richardson

  DOI：10.1055/s-2006-926307

  日期：——

  malononitriles has been developed. In this method, sodium borohydride in isopropanol has a catalytic effect on the initial condensation between malononitrile and aldehydes or ketones at 0 °C. The sodium borohydride also simultaneously acts as a reagent and reduces the unsaturated intermediate formed in situ by the condensation. This simple reductive alkylation method effectively consumes all malononitrile

  开发了一种高效、简便的单取代丙二腈的合成方法。在该方法中，异丙醇中的硼氢化钠对丙二腈与醛或酮在0℃下的初始缩合具有催化作用。硼氢化钠还同时充当试剂并还原通过缩合原位形成的不饱和中间体。这种简单的还原烷基化方法有效地消耗了所有丙二腈并选择性地仅生产单取代的丙二腈。通过这些单取代衍生物的烷基化制备不对称二取代丙二腈。
• Potassium tert-Butoxide Mediated Arylation of 2-Substituted Malononitriles Using Diaryliodonium Salts
  作者：Jianwei Han、Limin Wang、Xiaofei Qian、Bowen Xu

  DOI：10.1055/s-0036-1589061

  日期：2017.10

  Direct arylation of 2-substituted malononitriles using diaryliodonium salts without involving transition-metal catalysts was developed. By using potassium tert-butoxide as a promoter, the desired 2-substituated α-arylmalononitriles derivatives were synthesized in good to excellent yields of 55–96%. This synthetic method provided an efficient way to prepare a variety of 2-substituted arylmalononitriles

  开发了使用二芳基碘鎓盐直接芳基化 2-取代丙二腈而不涉及过渡金属催化剂。通过使用叔丁醇钾作为促进剂，合成了所需的 2-取代 α-芳基丙二腈衍生物，产率高达 55-96%。该合成方法为制备多种可用于农用化学品的2-取代芳基丙二腈提供了一种有效的方法。
• A Convenient Heterogeneous Reduction of Knoevenagel Product by Hantzsch Ester and Its Development into Reductive Alkylation of Malononitrile
  作者：Yong-Qing Yang、Zheng Lu

  DOI：10.1002/cjoc.201400144

  日期：2014.7

  Poor solubility of Hantzsch ester is used as indicator in the reduction of methylidene malononitrile. The Knoevenagel reaction is integrated to develop a reductive alkylation of malononitrile with aryl and aliphatic aldehyde as the carbonyl substrate.

  Hantzsch酯的溶解性差可作为还原亚甲基丙二腈的指标。整合Knoevenagel反应，以芳基和脂族醛为羰基底物，开发丙二腈的还原烷基化反应。
• Phosphoramidites Are Efficient, Green Organocatalysts for the Michael Reaction. Mechanistic Insights into the Phosphorus-Catalyzed Michael Reaction of Alkynones and Implications for Asymmetric Catalysis
  作者：Robert B. Grossman、Sébastien Comesse、Ravindra M. Rasne、Kazuyuki Hattori、Matthew N. Delong

  DOI：10.1021/jo026425g

  日期：2003.2.1

  Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, (x-cyano, esters, beta-keto esters, and nitro compounds. The relatively nontoxic, easily hydrolyzed HMPT catalyzes the Michael reaction within seconds at room temperature in the absence of a solvent, and the reaction is worked up simply by removing the catalyst in vacuo. The Michael reactions of alkynones, unlike those of alkenones, are shown to be irreversible. The implications for asymmetric catalysis are discussed.
• Echevarria Aurea, Martin Manuel, Perez Concepcion, Rozas Isabel, Arch. Pharm, 327 (1994) N 5, S 303-305
  作者：Echevarria Aurea, Martin Manuel, Perez Concepcion, Rozas Isabel

  DOI：——

  日期：——