2-(3-fluorobenzyl)malononitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-fluorobenzyl)malononitrile
• 英文别名: 2-[(3-Fluorophenyl)methyl]propanedinitrile
• 化学式: C₁₀H₇FN₂
• 分子量: 174.177
• InChiKey: MJCKEPFXEULRBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-fluorobenzyl)malononitrile 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以44%的产率得到4-(3-fluorobenzyl)-1H-pyrazole-3,5-diamine
  参考文献：
  名称：

  The Synthesis of Some Derivatives Based on the 4-Benzyl-1H-pyrazole-3,5-diamine Core

  摘要：

  The three-step synthesis of 4-benzyl-1H-pyrazole-3,5-diamines 2 from commercially available aldehydes 3 is given. The Knoevenagel condensation was utilized to assemble the initial carbon framework, resulting in the benzylidenemalononitriles 4 which were directly transformed by the reduction of the electron deficient C=C bond to benzylmalononitriles 5. Subsequent cycloaddition of hydrazine with 5 afforded the desired pyrazoles 2. Due to the high similarity with 4-arylazo-1H-pyrazole-3,5-diamines, the biological activities of the 4-benzyl-1H-pyrazole-3,5-diamines 2 were evaluated while focusing on the inhibition of cyclin-dependent kinases (CDKs), but no significant results were obtained.

  DOI：

  10.3987/com-10-12101
• 作为产物：
  描述：

  ((3-氟苯基)亚甲基)甲烷-1,1-二甲腈 在 polysiloxane-supported 1-benzyl-1,4-dihydronicotinamide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到2-(3-fluorobenzyl)malononitrile
  参考文献：
  名称：

  聚硅氧烷负载的NAD（P）H模型1-苄基-1,4-二氢烟酰胺：合成及其在还原活性烯烃中的应用。

  摘要：

  设计并合成了一种新型的聚硅氧烷支撑的NAD（P）H模型，即1-苄基-1,4-二氢烟酰胺，可在温和条件下有效还原许多活化烯烃。这种新型的聚硅氧烷支持的还原剂的最大优势在于：（i）易于处理和分离反应产物；（ii）还原剂具有良好的回收利用潜力，这使得这种新型的聚硅氧烷支持的NAD（P）H模型成为在研究实验室和工业过程中都有希望的替代方法。

  DOI：

  10.1021/jo020319x

文献信息

• Novel Pyrimidine- And Triazine-Hepcidine Antagonists
  申请人：Dürrenberger Franz

  公开号：US20120202806A1

  公开（公告）日：2012-08-09

  The present invention relates to new hepcidin antagonists, pharmaceutical compositions containing them and the use thereof as a drug, in particular for the treatment of iron metabolism disorders such as, in particular, iron deficiency diseases and anaemia, in particular anaemia associated with chronic inflammatory disease (ACD: anaemia of chronic disease and AI: anaemia of inflammation).

  本发明涉及新的肝铁蛋白拮抗剂，包含它们的药物组合物以及将其用作药物的用途，特别是用于治疗铁代谢紊乱，如特别是铁缺乏病和贫血，特别是与慢性炎症性疾病相关的贫血（ACD：慢性疾病性贫血和AI：炎症性贫血）。
• Polysiloxane-Supported NAD(P)H Model 1-Benzyl-1,4-dihydronicotinamide:  Synthesis and Application in the Reduction of Activated Olefins
  作者：Baolian Zhang、Xiao-Qing Zhu、Jin-Yong Lu、Jiaqi He、Peng G. Wang、Jin-Pei Cheng

  DOI：10.1021/jo020319x

  日期：2003.4.1

  A new polysiloxane-supported NAD(P)H model, 1-benzyl-1,4-dihydronicotinamide, was designed and synthesized, which can efficiently reduce many activated olefins under mild conditions. The most advantageous features of this new polysiloxane-supported reductant are (i) easy workup and separation of the reaction products and (ii) good potential for recycling use of the reductant, which makes this new

  设计并合成了一种新型的聚硅氧烷支撑的NAD（P）H模型，即1-苄基-1,4-二氢烟酰胺，可在温和条件下有效还原许多活化烯烃。这种新型的聚硅氧烷支持的还原剂的最大优势在于：（i）易于处理和分离反应产物；（ii）还原剂具有良好的回收利用潜力，这使得这种新型的聚硅氧烷支持的NAD（P）H模型成为在研究实验室和工业过程中都有希望的替代方法。
• Asymmetric Mannich Reaction of N-Boc Imines with Alkylmalononitriles Catalyzed by Dinuclear PhosphoiminoBINOL-Pd Complex
  作者：Takayoshi Arai、Ayu Nakamura

  DOI：10.1055/s-0037-1611842

  日期：2019.7

  PhosphoiminoBINOL-Pd2(OAc)2 complex catalyzed asymmetric Mannich reaction of N-Boc imines with alkyl malononitriles, with assistance of Zn(OAc)2 gave chiral amines with adjacent all-carbon quaternary carbon centers in up to 99% yield with 94% ee.

  PhosphoiminoBINOL-Pd2(OAc)2 配合物催化 N-Boc 亚胺与烷基丙二腈的不对称曼尼希反应，在 Zn(OAc)2 的帮助下得到具有相邻全碳季碳中心的手性胺，产率高达 99%，ee 为 94% .
• Chiral Dinuclear Benzyliminobinaphthoxy‐Palladium Catalyst for Asymmetric Mannich Reaction of Aldimines and Isatin‐Derived Ketimines with Alkylmalononitriles
  作者：Ayu Nakamura、Satoru Kuwano、Junchuan Sun、Kensuke Araseki、Eri Ogino、Takayoshi Arai

  DOI：10.1002/adsc.202000447

  日期：2020.8.4

  A newly developed dinuclear bis(benzylimino)binaphthol (BIB )−Pd complex showed good catalytic activity for the Mannich reaction of aldimines and isatin‐derived ketimines with alkylmalononitriles to give the products in a highly enantioselective manner.

  一种新开发的双核双（苄基亚氨基）联萘酚（BIB）-Pd络合物对醛亚胺和源自靛红的酮亚胺与烷基丙二腈的曼尼希反应具有良好的催化活性，从而以高度对映选择性的方式提供了产物。
• Zhu, Xiao-Qing; Zou, Hong-Ling; Yuan, Ping-Wei, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 9, p. 1857 - 1861
  作者：Zhu, Xiao-Qing、Zou, Hong-Ling、Yuan, Ping-Wei、Cao, Lei、Cheng, Jin-Pei

  DOI：——

  日期：——