3-ethoxy-4-hydroxybenzylidenemalononitrile | 15728-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethoxy-4-hydroxybenzylidenemalononitrile
• 英文别名: (3-ethoxy-4-hydroxy-benzylidene)-malononitrile；(3-Aethoxy-4-hydroxy-benzyliden)-malononitril；2-(4-Hydroxy-3-ethoxy-benzyliden)-malonsaeure-dinitril；(3-Ethoxy-4-hydroxy-benzyliden)-malonsaeure-dinitril；3-Ethoxy-4-hydroxy-benzalmalonitril；(3-Ethoxy-4-hydroxybenzylidene)malononitrile；2-[(3-ethoxy-4-hydroxyphenyl)methylidene]propanedinitrile
• CAS: 15728-34-4
• 化学式: C₁₂H₁₀N₂O₂
• mdl: MFCD00811572
• 分子量: 214.224
• InChiKey: NICBMMKNBWCVPN-UHFFFAOYSA-N

物化性质

• 熔点：
  161.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  390.5±37.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethoxy-4-hydroxybenzylidenemalononitrile 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以45%的产率得到2-[[3-[5-(2,2-Dicyanoethenyl)-3-ethoxy-2-hydroxyphenyl]-5-ethoxy-4-hydroxyphenyl]methylidene]propanedinitrile
  参考文献：
  名称：

  Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents

  摘要：

  Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3 -methoxy-1-(substituted-vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted-vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-alpha, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autaphosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 mu M tamoxifen, suggesting that this compound has estrogen agonist activity.

  DOI：

  10.1021/jm990947f
• 作为产物：
  描述：

  乙基香兰素 、 丙二腈 在 C₄₄H₅₂CuN₈S₄⁽¹⁺⁾*BF₄^(1-) 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以74%的产率得到3-ethoxy-4-hydroxybenzylidenemalononitrile
  参考文献：
  名称：

  使用各种醛和活性亚甲基化合物的高活性铜 (I)-硫属元素酮催化 Knoevenagel 缩合反应

  摘要：

  已经报道了第一个铜 (I) 硫属元素酮催化的 Knoevenagel 缩合反应。没有发现在 Knoevenagel 缩合催化中使用这种铜-硫属元素酮络合物类的说明。因此，铜(I)双(苯并咪唑-2-硫属元素酮)催化剂[Cu( L 1 ) 4 ] + BF 4 - ( 1 ) 和[Cu( L 2 ) 4 ] + BF 4 - ( 2 ) ( L 1  =双(1-异丙基-苯并咪唑-2-selone)-3-乙基；L 2 =双（1-异丙基-苯并咪唑-2-硫酮）-3-乙基）已被用作Knoevenagel缩合反应中的催化剂。这些铜 (I) 硫属元素酮催化剂在芳基醛和活性亚甲基化合物的催化 Knoevenagel 缩合反应中表现出高效率。特别是配合物2表现出最好的催化活性。已经用 22 种不同的分子研究了催化反应的范围。已经描述了具有富电子或缺乏芳基醛的各种类型的底物的优异催化活性。本研究的特点是反应条件

  DOI：

  10.1007/s10562-021-03810-6

文献信息

• Knoevenagel condensation reaction on a new highly-efficient La2O2CO3-TiO2 mixed oxide catalyst: Composition-effects on C C bond formation
  作者：Fei Wang、Kai Hu、Yanshuai Bi、Xuejiao Wei、Bing Xue

  DOI：10.1016/j.chemphys.2020.110942

  日期：2020.11

  due to cooperative interactions between acid and base functional groups present in their active sites. New La2O2CO3-TiO2 mixed oxide catalysts with different La/Ti molar ratios successfully synthesized through a facile solvothermal method were investigated for the Knoevenagel condensation reaction of various carbonyl compounds derivatives with malononitrile. The analytical determinations, including

  一些混合氧化物的高效催化能力是由于其活性位点中存在的酸与碱官能团之间的协同相互作用。通过简便的溶剂热方法成功地合成了具有不同La / Ti摩尔比的新型La 2 O 2 CO 3 -TiO 2混合氧化物催化剂，用于各种羰基化合物衍生物与丙二腈的Knoevenagel缩合反应。X 2，拉曼，HRTEM，CO 2和NH 3的N 2吸附/解吸和TPD的分析测定结果证明了所制备的La 2 O 2 CO的结构特征。3- TiO 2混合氧化物催化剂。具有摩尔比La / La + Ti ＝ 0.09组成的La 2 O 2 CO 3 -TiO 2混合氧化物催化剂（La 2 O 2 CO 3（0.09）-TiO 2）对于苯甲醛与丙二腈的Knoevenagel反应显示出最高的苯甲醛转化率。更重要的是，该催化剂可以成功地用于各种羰基化合物衍生物的Knoevenagel缩合反应，收率高于85％。La 2 O 2 CO
• Sidhu, Anjali; Sharma; Rai, Mangat, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 2, p. 247 - 250
  作者：Sidhu, Anjali、Sharma、Rai, Mangat

  DOI：——

  日期：——
• Notes- Synthesis of Some Aromatic Malononitriles
  作者：Raymond Mariella、Joseph Bauer

  DOI：10.1021/jo01095a623

  日期：1958.1
• Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents
  作者：Geoffrey Wells、Angela Seaton、Malcolm F. G. Stevens

  DOI：10.1021/jm990947f

  日期：2000.4.1

  Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3 -methoxy-1-(substituted-vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted-vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-alpha, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autaphosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 mu M tamoxifen, suggesting that this compound has estrogen agonist activity.
• Highly Active Copper(I)-Chalcogenone Catalyzed Knoevenagel Condensation Reaction Using Various Aldehydes and Active Methylene Compounds
  作者：Maruthupandi Mannarsamy、Ganesan Prabusankar

  DOI：10.1007/s10562-021-03810-6

  日期：2022.8

  have been utilized as catalysts in the Knoevenagel Condensation reactions. These copper(I) chalcogenone catalysts have shown high efficiency for the catalytic Knoevenagel Condensation of aryl aldehydes and active methylene compounds. In particular, complex 2, exhibit the best catalytic activities. The scope of the catalytic reactions has been investigated with 22 different molecules. The excellent

  已经报道了第一个铜 (I) 硫属元素酮催化的 Knoevenagel 缩合反应。没有发现在 Knoevenagel 缩合催化中使用这种铜-硫属元素酮络合物类的说明。因此，铜(I)双(苯并咪唑-2-硫属元素酮)催化剂[Cu( L 1 ) 4 ] + BF 4 - ( 1 ) 和[Cu( L 2 ) 4 ] + BF 4 - ( 2 ) ( L 1  =双(1-异丙基-苯并咪唑-2-selone)-3-乙基；L 2 =双（1-异丙基-苯并咪唑-2-硫酮）-3-乙基）已被用作Knoevenagel缩合反应中的催化剂。这些铜 (I) 硫属元素酮催化剂在芳基醛和活性亚甲基化合物的催化 Knoevenagel 缩合反应中表现出高效率。特别是配合物2表现出最好的催化活性。已经用 22 种不同的分子研究了催化反应的范围。已经描述了具有富电子或缺乏芳基醛的各种类型的底物的优异催化活性。本研究的特点是反应条件