2-(2-fluorobenzyl)malononitrile | 338965-16-5

• 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-(2-fluorobenzyl)malononitrile
• 英文别名: 2-[(2-Fluorophenyl)methyl]propanedinitrile
• CAS: 338965-16-5
• 化学式: C₁₀H₇FN₂
• mdl: MFCD00231635
• 分子量: 174.177
• InChiKey: BPZXOWTXLOQRJA-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  339.5±27.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

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-(2-fluorobenzyl)malononitrile 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以67%的产率得到4-(2-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：

  2-[(2-氟苯基)亚甲基]丙二腈 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以0.6 g的产率得到2-(2-fluorobenzyl)malononitrile
  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

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）。
• 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。
• Chiral Primary Amine Catalyzed Asymmetric Michael Addition of Malononitrile to α-Substituted Vinyl Ketone
  作者：Niankai Fu、Long Zhang、Sanzhong Luo

  DOI：10.1021/ol503566a

  日期：2015.1.16

  The first efficient and highly enantioselective Michael addition–protonation reaction of malononitriles to α-substituted vinyl ketones has been developed by using a chiral primary amine as the organocatalyst. With a Hantzsch ester as the hydride source, an enantioselective tandem reduction, Michael addition–protonation reaction of benzylidenemalononitrile has also been achieved with good yields and

  通过使用手性伯胺作为有机催化剂，开发了丙二腈向α-取代的乙烯基酮的第一个高效且高度对映选择性的迈克尔加成-质子化反应。以Hantzsch酯为氢化物源，可实现对映选择性串联还原，还实现了苄基丙二腈的迈克尔加成-质子化反应，收率高，对映选择性高。
• PYRIMIDINE ALS HEPCIDIN-ANTAGONISTEN
  申请人：VIFOR (INTERNATIONAL) AG

  公开号：EP2473486B1

  公开（公告）日：2015-10-28