2-(3,4-dichlorobenzyl)-malononitrile | 474759-80-3

• 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-(3,4-dichlorobenzyl)-malononitrile
• 英文别名: 3,4-dichlorobenzylmalonodinitrile；(3,4-Dichlorobenzyl)malononitrile；2-[(3,4-dichlorophenyl)methyl]propanedinitrile
• CAS: 474759-80-3
• 化学式: C₁₀H₆Cl₂N₂
• 分子量: 225.077
• InChiKey: ONTUBZPGRNHELJ-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  400.5±40.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,4-dichlorobenzyl)-malononitrile 、 2-[(三氟甲基)硫代]乙醇 在 二溴亚砜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.33h， 以40%的产率得到2-(3,4-dichloro-benzyl)-2-(2-trifluoromethylsulfanyl-ethyl)-malononitrile
  参考文献：
  名称：

  WO2007/71609

  摘要：

  公开号：
• 作为产物：
  描述：

  3,4-二氯苯甲醛 、 丙二腈 在 二氢吡啶 作用下， 反应 1.5h， 以95%的产率得到2-(3,4-dichlorobenzyl)-malononitrile
  参考文献：
  名称：

  Solvent-free mechanochemical and one-pot reductive benzylizations of malononitrile and 4-methylaniline using Hantzsch 1,4-dihydropyridine as the reductant

  摘要：

  在机械研磨条件下，以 1,4-二氢吡啶为还原剂，实现了芳香醛对丙二腈和 4-甲基苯胺的直接还原苄化。

  DOI：

  10.1039/b502662h

文献信息

• Malononitrile compounds and their use as pesticides
  申请人：——

  公开号：US20040138065A1

  公开（公告）日：2004-07-15

  The present invention relates to malononitrile compounds of formula 1 wherein R 1 and R 2 are the same or different and independently C 1 -C 5 (halo)alkyl, C 1 -C 5 (halo)alkyloxy, C 2 -C 5 (halo)alkenyl, C 2 -C 5 (halo)alkynyl, hydrogen, or cyano; R 3 is C 1 -C 3 haloalkyl, C 2 -C 4 haloalkenyl, or C 2 -C 4 haloalkynyl; m is an integer of 1 to 3; R 3 is halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, or the like; n is an integer of 0 to 4, with the proviso that when n is 2 or more, then R 5 's are the same or different from each other; R 6 is hydrogen, halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, or the like; as well as pesticide compositions containing these compounds as active ingredients. The present invention makes it possible to effectively control pests such as insect pests, acarine pests, and nematode pests.

  本发明涉及公式1的马隆腈化合物，其中R1和R2相同或不同且独立地为C1-C5（卤）烷基，C1-C5（卤）烷氧基，C2-C5（卤）烯基，C2-C5（卤）炔基，氢或氰基；R3为C1-C3卤代烷基，C2-C4卤代烯基或C2-C4卤代炔基；m为1到3的整数；R4为卤素，氰基，硝基，C1-C4（卤）烷基或类似物；n为0到4的整数，但当n为2或更多时，R5相互之间相同或不同；R6为氢，卤素，氰基，硝基，C1-C4（卤）烷基或类似物；以及含有这些化合物作为活性成分的杀虫剂组合物。本发明使得能够有效地控制昆虫害虫、螨虫和线虫害虫。
• Pesticide composition comprising malononitrile compounds
  申请人：——

  公开号：US20040142821A1

  公开（公告）日：2004-07-22

  The present invention relates to use of malononitrile compounds of formula (X): 1 wherein R 1 and R 2 are the same or different and independently C 1 -C 5 (halo)-alkyl, C 1 -C 5 (halo)alkyloxy, C 2 -C 5 (halo)alkenyl, C 2 -C 5 (halo)alkynyl, hydrogen, or cyano; R 3 and R 4 are the same or different and independently C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, or hydrogen, or R 3 and R 4 are taken together to form C 2 -C 6 (halo)alkylene or C 4 -C 6 (halo)alkenylene; R 5 is halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, or the like; n is an integer of 0 to 4; R 6 is halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, or the like; or R 5 and R 6 are taken together to form methylenedioxy; with the provisos that when R 6 is hydrogen, then n is an integer of 1 to 4 and that when n is 2 or more, then R 5 's are different from each other; as pesticides, and to pesticide compositions containing these compounds as active ingredients. The present invention makes it possible to effectively control pests such as insect pests, acarine pests, and nematode pests.

  本发明涉及使用式（X）的丙二腈化合物：其中R1和R2相同或不同且独立地为C1-C5（卤）烷基，C1-C5（卤）烷氧基，C2-C5（卤）烯基，C2-C5（卤）炔基，氢或氰基；R3和R4相同或不同且独立地为C1-C10烷基，C2-C10烯基，C2-C10炔基或氢，或者R3和R4结合形成C2-C6（卤）烷基或C4-C6（卤）烯基；R5为卤素，氰基，硝基，C1-C4（卤）烷基或类似物；n为0至4的整数；R6为卤素，氰基，硝基，C1-C4（卤）烷基或类似物；或者R5和R6结合形成亚甲二氧基；但当R6为氢时，n为1至4的整数，且当n为2或更多时，R5不相同；作为杀虫剂，以及含有这些化合物作为活性成分的杀虫剂组合物。本发明使得能够有效地控制害虫，例如昆虫害虫，螨虫害虫和线虫害虫。
• Malononitrile Compounds
  申请人：Pohlman Matthias

  公开号：US20090326012A1

  公开（公告）日：2009-12-31

  Compounds of formula I wherein X is O or S(═O) n ; n is 0, 1 or 2; R 1 is optionally substituted alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, cycloalkenyl, halocycloalkenyl, phenyl, hetaryl, phenylalkyl, hetaryl alkyl, optionally fused to phenyl, hetaryl or heterocyclyl; A is —NR b 2 , —C(=G)GR b , —C(=G)NR b 2 , —C(═NOR b )R b , C(=G)[N═SR b 2 ], —C(=G)NR b —NR 2 , C 2 -C 6 -alkandiyl, C 2 -C 6 -alkenediyl, C 1 -C 3 -alkyl-G-C 1 -C 3 -alkyl, wherein R b is as defined in the description, or optionally substituted phenyl, hetaryl, heterocyclyl, optionally fused to phenyl or heterocyclyl; B is an optionally substituted saturated or partially unsaturated hydrocarbon chain with 1 to 3 carbon chain atoms; D is an optionally substituted saturated or partially unsaturated hydrocarbon chain with 1 to 5 carbon chain atoms or C 3 -C 6 -cycloalkyl; G is oxygen or sulfur; or the enantiomers or diastereomers or salts or N-oxides thereof, processes for preparing the compounds I, pesticidal compositions and synergistic mixtures comprising compounds I, methods for the control of insects, acarids or nematodes by contacting the pests or their food supply, habitat or breeding grounds with a pesticidally effective amount of compounds formula I, and a method for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of compounds of formula I.

  公式I的化合物，其中X为O或S（═O）n; n为0、1或2; R1是可选取代的烷基、卤代烷基、烯基、卤代烯基、炔基、卤代炔基、环烷基、卤代环烷基、环烯基、卤代环烯基、苯基、杂环基、苯基烷基、杂环基烷基，可选择与苯基、杂环基或杂环基融合; A为—NRb2、—C（=G）GRb、—C（=G）NRb2、—C（═NORb）Rb、C（=G）[N═SRb2]、—C（=G）NRb—NR2、C2-C6-烷二基、C2-C6-烯二基、C1-C3-烷基-G-C1-C3-烷基，其中Rb在描述中定义，或可选取代的苯基、杂环基、杂环基，可选择与苯基或杂环基融合; B为可选取代的饱和或部分不饱和的碳链，具有1至3个碳链原子; D为可选取代的饱和或部分不饱和的碳链，具有1至5个碳链原子或C3-C6-环烷基; G为氧或硫; 或其对映体或顺反异构体或盐或N-氧化物，制备化合物I的过程，包含化合物I的杀虫剂组合物和协同混合物，通过将化合物公式I的杀虫剂有效量与害虫或其食物供应、栖息地或繁殖场所接触的方法来控制昆虫、螨或线虫的方法，以及治疗、控制、预防或保护动物免受寄生虫侵袭或感染的方法，其中包括口服、局部或肌肉注射或应用化合物I的寄生虫有效量。
• 10.1021/acs.orglett.4c01415
  作者：Zhou, Yangkun、Huang, Hanmin

  DOI：10.1021/acs.orglett.4c01415

  日期：——

  efficient reductive dicarbofunctionalization of unactivated alkenes with alkyl halides and malononitriles. The combination of Ni electron-shuttle catalysis with Eu(OTf)3, a non-redox-type Lewis acid, effectively activates the iminyl radicals, enabling the direct formation of the C(sp3)–C(sp3) bond and β-ketonitrile functionality across a variety of C═C double bonds. This reaction allows for the expedient

  开发了一种二元 Ni/Eu 催化系统，该系统能够利用烷基卤和丙二腈对未活化的烯烃进行有效的还原双碳官能化。 Ni电子穿梭催化与非氧化还原型路易斯酸Eu(OTf) 3的结合，有效激活亚胺基自由基，从而能够直接形成C(sp 3 )–C(sp 3 )键和β -酮腈官能团跨越各种C=C双键。该反应可以方便地合成带有全碳四元中心的密集官能化环状β-酮腈。
• EP1385377A1
  申请人：——

  公开号：EP1385377A1

  公开（公告）日：2004-02-04