(2,4-dimethylbenzylidene)malononitrile | 75076-12-9

• 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: (2,4-dimethylbenzylidene)malononitrile
• 英文别名: 2-(2,4-dimethylbenzylidene)malononitrile；2-[(2,4-Dimethylphenyl)methylidene]propanedinitrile
• CAS: 75076-12-9
• 化学式: C₁₂H₁₀N₂
• mdl: MFCD00466526
• 分子量: 182.225
• InChiKey: OCKQQTWVONOSPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C(Solv: isopropanol (67-63-0))
• 沸点：
  321.9±37.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 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：

  白杨素 、 (2,4-dimethylbenzylidene)malononitrile 在 calcium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以80%的产率得到2-amino-4-(2,4-dimethylphenyl)-5-hydroxy-6-oxo-8-phenyl-4H-pyrano[3,2-g]chromene-3-carbonitrile
  参考文献：
  名称：

  Regioselective synthesis and evaluation of 2-amino 3-cyano chromene-chrysin hybrids as potential anticancer agents

  摘要：

  The first example of Ca(OH)(2)-activated p-regioselective synthesis of chrysin-fused chromene was reported through a cascade Michael/cyclization of chrysin and arylidenemalononitrile. The newly synthesized structurally diverse 2-amino 3-cyano chromene-chrysin hybrids 3 were evaluated for their in vitro anticancer activity, and some of the compounds showed stronger anti-proliferative activity against K562, PC-3, A549 and NCI-H1299 than parent compound chrysin, and demonstrated equipotent potency compared with the reference drug of cisplatin. In particular, compound 3h had the highest cytotoxicity towards K562 cells (IC50 = 6.41 mu M). Furthermore, compound 3h induced apoptosis of K562 cells in a concentration-dependent manner, as well as induced the apoptosis possibly through promoting the formation of apoptotic DNA of cancer cell via the intrinsic apoptotic pathway. Thus, our results provide in vitro evidence that compound 3h may be a potential candidate for the development of new anti-tumour drugs.

  DOI：

  10.1016/j.bmcl.2020.127087
• 作为产物：
  描述：

  2,4-二甲氧基苯甲醛 生成 (2,4-dimethylbenzylidene)malononitrile
  参考文献：
  名称：

  Pyridine and pyrimidine derivatives

  摘要：

  本发明提供了化合物的公式（I）1，其中R1、R2、R3、R4和X如规范中所定义，以及其药用盐。这些化合物可用于治疗和/或预防与DPP IV相关的疾病，如糖尿病，特别是非胰岛素依赖型糖尿病和糖耐量受损。

  公开号：

  US20030216382A1

文献信息

• Molybdenum carbide as an efficient and durable catalyst for aqueous Knoevenagel condensation
  作者：Mina Tavakolian、Mohammad Mahdi Najafpour

  DOI：10.1039/c9nj04647j

  日期：——

  and benign catalysts were used for the Knoevenagel condensation reaction. Among the compounds (Mo2C, MoS2, MoB, MoSi2), molybdenum carbide showed efficient performance for the Knoevenagel condensation in aqueous media at room temperature, affording the corresponding products in high yields within a short reaction time. Notably, using this commercially available heterogeneous catalyst, the deaceta

  遵循绿色化学原理，各种经济高效的钼化合物，可商购的非均相和良性催化剂被用于Knoevenagel缩合反应。在化合物（Mo 2 C，MoS 2，MoB，MoSi 2），碳化钼在室温下在水性介质中对Knoevenagel缩合反应表现出有效的性能，可在较短的反应时间内以高收率提供相应的产物。值得注意的是，使用这种可商购的非均相催化剂，苯甲醛二甲基乙缩醛和丙二腈在室温下的脱缩醛-Knoevenagel缩合可以成功地以优异的产率进行。通过操作简单的程序，碳化钼可以回收五次而不会失去活性。
• Facile synthesis of pure non-monoclinic zirconia nanoparticles and their catalytic activity investigations for Knoevenagel condensation
  作者：Reihaneh Malakooti、Hesamaldin Mahmoudi、Rahele Hosseinabadi、Srebri Petrov、Andrea Migliori

  DOI：10.1039/c3ra44682d

  日期：——

  Unlike previous approaches, our synthesis of the catalytically relevant (tetragonal and/or cubic) phase of this material did not require (i) an annealing step to stabilize the tetragonal phase, or (ii) the inclusion of dopants. Furthermore, these high surface area tetragonal zirconia nanoparticles showed a good catalytic activity towards the Knoevenagel condensation.

  氧化锆纳米颗粒是在油胺和油酸存在下，通过八水合氯化锆的非水解热分解合成的。通过XRD、HR-TEM和EDAX技术对纳米颗粒进行表征。TEM观察证实纳米颗粒具有近似球形，平均尺寸为3-4 nm，具有非单斜结构。与以前的方法不同，我们合成该材料的催化相关（四方和/或立方）相不需要（i）退火步骤来稳定四方相，或（ii）包含掺杂剂。此外，这些高表面积四方氧化锆纳米颗粒对 Knoevenagel 缩合表现出良好的催化活性。
• Bis-Functionalization of 1,3-Dienes through 1,4-Conjugate Addition of Amphiphilic Bis-π-Allyl and Related Palladium Intermediates
  作者：K. Radhakrishnan、Yoshinori Yamamoto、T. Baiju、Ajesh Vijayan、Nayana Joseph、Preethanuj Preethalayam、E. Suresh

  DOI：10.1055/s-0033-1340171

  日期：——

  three-component coupling of allylstannane, allyl chloride and a functionalized diene is described. Regioselective 1,4-functionalization of the Michael acceptor 1,3-diene is accomplished by the amphiphilic bis-π-allylpalladium complex. To the best of our knowledge, this is the first time a functionalized 1,3-butadiene has been used as a Michael acceptor. The scope of the present strategy is further extended to 1

  描述了钯催化的烯丙基锡烷、烯丙基氯和官能化二烯的三组分偶联。迈克尔受体 1,3-二烯的区域选择性 1,4-官能化由两亲性双-π-烯丙基钯配合物完成。据我们所知，这是第一次使用功能化的 1,3-丁二烯作为迈克尔受体。本策略的范围进一步扩展到功能化二烯的 1,4-烯丙基化-氧基烯丙基化。
• Oxygen Switch in Visible-Light Photoredox Catalysis: Radical Additions and Cyclizations and Unexpected C–C-Bond Cleavage Reactions
  作者：Shaoqun Zhu、Arindam Das、Lan Bui、Hanjun Zhou、Dennis P. Curran、Magnus Rueping

  DOI：10.1021/ja309580a

  日期：2013.2.6

  oxygen, a radical addition/cyclization reaction occurred which resulted in the formation of tetrahydroquinoline derivatives in good yields under mild reaction conditions. The intramolecular version of the radical addition led to the unexpected formation of indole-3-carboxaldehyde derivatives. Mechanistic investigations of this reaction cascade uncovered a new photoredox catalyzed C-C bond cleavage reaction

  已经开发出可见光光氧化还原催化的叔胺的分子间和分子内 CH 官能化反应。发现氧气作为化学开关触发两种不同的反应途径，并从相同的起始材料中获得两种不同类型的产物。在没有氧气的情况下，N,N-二甲基-苯胺与缺电子烯烃的分子间加成以良好到高产率提供了γ-氨基腈。在氧气存在下，发生自由基加成/环化反应，导致在温和的反应条件下以良好的产率形成四氢喹啉衍生物。自由基加成的分子内形式导致了 indole-3-carboxaldehyde 衍生物的意外形成。
• Metal-free, atom and redox-economical construction of C–C bonds enabled by oligofluorene-containing hypercrosslinked polymers
  作者：Feng Lan、Cen Zhou、Xiaozhou Huang、Bohang An、Xiao Zhang

  DOI：10.1039/d2gc00107a

  日期：——

  A metal-free, atom and redox-economical approach for the assembly of C–C bonds has been developed using oligofluorene-based hypercrosslinked polymers as the recoverable and reusable photocatalysts under visible-light irradiation.

  已开发出一种无金属、原子和氧化还原经济的方法，利用基于寡萤光烯的超交联聚合物作为可回收和可重复使用的光催化剂，在可见光照射下组装C-C键。